Category: 37480-41-4

Rubin, Martin; Wishinsky, Henry published an article in 1946, the title of the article was 1-Methyl-3-ethyl-4-(p-hydroxyphenyl)-Δ3-cyclohexenylethylcarbinol, an “open model” of estradiol.COA of Formula: C9H14O3 And the article contains the following content:

Johnson and Offenhauer (C.A. 39, 4067.1) have suggested 4-(p-hydroxyphenyl)hexahydropropio-phenone as an “open model” of estrone; [1-methyl-3-ethyl-4-(p-hydroxyphenyl)-3-cyclohexenyl]ethylcarbinol (I) is now proposed as an open model of estradiol. γ-Methyl-γ-carboxypimelic acid (II) yields 80% of the Et ester, b0.1 128-31°, which is cyclized (75%) to Et 1-methyl-3-carbethoxy-4-ketocyclohexanecarboxylate (II), b0.2 125-30°, gives a violet color with FeCl3. II (10 g.) in 20 cc. AcOH, 5 cc. concentrated HCl, and 3 cc. H2O, refluxed 5 h., gives 78% of 1-methyl-4-ketocyclohexanecarboxylic acid (III), b0.5 130-5°, m. 78-9°. III results in 47% yield by refluxing 15 g. I and 30 g. Ac2O for 4 h. and heating the residue at 200-20°/30 mm. until CO2 evolution ceases. The Me ester (IV) of III b0.2 80-3°. II (130 g.), added to 11.5 g. Na in 300 cc. PhMe and refluxed until the Na has reacted, the solution treated with 100 g. EtI, and refluxed for 14 h., gives 92% of the 3-Et homolog of II, b0.1 120-5°; 130 g. in 400 cc. AcOH, 80 cc. concentrated HCl, and 32 cc. H2O, refluxed 18 h., gives 88% of the 3-Et homolog (V) of III, b0.1 140-50°; Me ester, b0.05 95°. The reaction product of 32 g. of V with p-MeOC6H4MgBr (from 35 g. p-MeO-C6H4Br) in ether (refluxing 2 h.), decomposed with dilute H2SO4, the ether layer extracted with 5% NaOH, the alk. extract acidified, extracted with ether, and the residue treated with CH2N2, gives 13 g. of the carbinol (with some dehydrated product), C18H26O4, b0.1 150-60°; dehydration with SOCl2-C5H5N and saponification with 10% NaOH in 50% MeOH give 15% of 1-methyl-3-ethyl-4-(p-methoxyphenyl)-3-cyclohexene-1-carboxylic acid (VI), m. 123-4°; this is resistant to catalytic hydrogenation over active Pt at room temperature and 30 lb. H pressure. VI (7 g.) in 50 cc. C6H6, treated with 10 cc. SOCl2 and a drop of C5H5N, allowed to stand overnight at room temperature, the residue in PhMe treated at 0-5° with an excess of Et2Zn in PhMe, the mixture allowed to warm to room temperature, and after 4 h. decomposed with EtOH and dilute HCl, gives 7 g. of 1-methyl-1-propionyl-3-ethyl-4-(p-methoxyphenyl)-3-cyclohexene, b0.1 150-5° (not anal. pure); this is not stable to acidic demethylation reagents but 5 g. with 5 g. KOH and 150 cc. C2H4-(OH)2, refluxed 4 h., gives 60% of I, pale yellow glass, b0.1 175-80° (p-nitrobenzoate, m. 127-8°). IV (34 g.) and p-MeOC6H4MgBr give 12 g. of 1-methyl-4-(p-methoxy-phenyl)-3-cyclohexene-1-carboxylic acid, (VII), m. 137-7.5°, and 6 g. of the lactone of 1-methyl-4-hydroxy-4-(p-methoxyphenyl)cyclohexanecarboxylic acid, m. 114-15°; the latter can be converted to VII by saponification with aqueous alkali, followed by distillation of the H2O in vacuo, then by heating with KHSO4 and tetralin for 1 h. Catalytic reduction of VII in AcOH over Pt oxide at room temperature and a pressure of 2 atm. gives 1-methyl-4-(p-methoxyphenyl)cyclohexane-carboxylic acid (VIII), m. 112-15°; Me ester, b0.1 140-5°. Reaction of the acid chloride of VIII with Et2Zn gives a crude 1-methyl-1-propionyl-4-(p-methoxyphenyl)cyclohexane, b0.03 140-5°; refluxed with 40% HBr in glacial AcOH, it yields 60% of 1-methyl-4-(p-hydroxyphenyl)-hexahydropropiophenone, m. 142-3°, purified through the benzoate, m. 96-7°. The experimental process involved the reaction of Methyl 1-methyl-4-oxocyclohexanecarboxylate(cas: 37480-41-4).COA of Formula: C9H14O3

Methyl 1-methyl-4-oxocyclohexanecarboxylate(cas:37480-41-4) belongs to ethers. Oxygen is more electronegative than carbon, thus the alpha hydrogens of ethers are more acidic than those of simple hydrocarbons. They are far less acidic than alpha hydrogens of carbonyl groups (such as in ketones or aldehydes), however. COA of Formula: C9H14O3

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Nazarov, I. N.; Zav’yalov, S. I. published an article in 1952, the title of the article was Acetylene derivatives. CXXVII. Synthesis of polycyclic compounds related to steroids. 15. Structure of products of condensation of 2-methoxy-1, 3-butadiene with 2-methyl-2-cyclohexen-1-one and methyl methacrylate.Reference of Methyl 1-methyl-4-oxocyclohexanecarboxylate And the article contains the following content:

cf. C.A. 44, 3458i; 46, 2088f; 47, 5366c; 9969b. Condensation of H2C:C(OMe)CH:CH2 with 2-methyl-2-cyclohexen-1-one as described earlier (loc. cit.) gave 8a-methyl-6-methoxy-Δ6-1-octalone, b0.1 88-9°, nD20 1.5089. This (10 g.) refluxed 3 h. with MeMgI, from 13 g. MeI, gave 4.8 g. 1, 8a-dimethyl-1-hydroxy-6-oxodecalin (I), b0.05 118-20°, nD20 1.5140, which on distillation tends to lose H2O, yielding the unsaturated ketone, 1, 8a-dimethyl-6-oxo-Δ1-octahydronaphthalene (II). I with powd. KHSO4 at 160° in vacuo gave some 66% (II), b4 104-8°, nD20 1.5099; semicarbazone, m. 172-4° (from MeOH). II with MeMgI gave some 90% 1,6,8a-trimethyl-6-hydroxy-Δ1-octahydronaphthalene (III), b3 100-5°, nD20 1.5104, which with KHSO4 at 165-75° gave 50% 1,6,8a-trimethyl-Δ1,6-hexahydronaphthalene (IV), b. 229-31°, nD20 1.5035, which, passed over Pd-C at 330°, gave 1,6-C10H6Me2, b13 130-3°, nD20 1.6078; picrate, m. 108-10°. MeMgI with hexahydro-8a-methyl-1,6-(2H, 5H)-naphthalenedione gave after 3 h. refluxing some 90% decahydro-1,6,8a-trimethyl-1, 6-naphthalenediol (V), b0.05 113-16°, nD20 1.5115. This with KHSO4 at 150-5° at 100 mm. gave 60% of a mixture of IV and the corresponding 1,6-oxide; the mixture over Pd-C as above gave 1,6-C10H6Me2. Heating 4 g. CH2:C(OMe)CH:CH2 with 4.8 g. CH2:CMeCO2H in the presence of a little pyrogallol in C6H6 3 h. in an ampul at 219-20° gave 5.2 g. Me 1-methyl-4-methoxy-3-cyclohexene-1-carboxylate (VI), b12 107-8°, nD20 1.4722, which, shaken with 1% HCl 4 h. gave Me 1-methyl-4-oxocyclohexanecarboxylate (VII), b7 99-101°, nD20 1.4610; semicarbazone, m. 166-8°; 2, 4-dinitrophenylhyrazone, m. 125-7° (cf. Rubin and Wishinsky, C.A. 40, 2117.7). This refluxed 6 h. with aqueous AcOH and concentrated HCl gave the free acid (VIII), m. 77-8°, b2 145-8°. Cyclization of MeO2CCMe(CH2CH2CO2Me)2 (loc. cit.) gave Me 1-methyl-4-oxo-1,3-cyclohexanedicarboxylate, b3 130-2°, nD20 1.4859, which, shaken 2-3 min. with 5% NaOH and let stand 8 h., gave the free acid, decompose 104-6° decarboxylated at 120° to VIII, m. 76-8°. With CH2N2 this gave VII. VI (10 g.) treated in CCl4 with ice cooling with 8.4 g. Br over 1 h., then shaken 15 min. with 62 mL. H2O, and the organic layer dried, evaporated, treated with 9.5 g. PhNEt2 at 150° 1 h., made acid to Congo red, with 1:1 HCl and extracted with C6H6 gave 4 g. Me 2-methyl-4-oxo-2-cyclohexene-1-carboxylate, b7 107-10°, nD20 1.4775; semicarbazone, m. 157-8°. This (4 g.) with NaCH(CO2Et)2 from 15 g. CH2(CO2Et)2 after 7 h. at 70-6° and acidification with 1:1 HCl, gave 2.2 g. di-Et 2-carbomethoxy-2-methyl-4-oxocyclopentanemalonate, b1.5 155-7°, nD20 1.4888. The experimental process involved the reaction of Methyl 1-methyl-4-oxocyclohexanecarboxylate(cas: 37480-41-4).Reference of Methyl 1-methyl-4-oxocyclohexanecarboxylate

Methyl 1-methyl-4-oxocyclohexanecarboxylate(cas:37480-41-4) belongs to ethers. Oxygen is more electronegative than carbon, thus the alpha hydrogens of ethers are more acidic than those of simple hydrocarbons. They are far less acidic than alpha hydrogens of carbonyl groups (such as in ketones or aldehydes), however. Reference of Methyl 1-methyl-4-oxocyclohexanecarboxylate

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

On September 22, 1976, Miki, Tosaku; Ineoka, Mari; Isoda, Yoshiro; Okano, Junji published a patent.COA of Formula: C9H14O3 The title of the patent was Active amino acid. And the patent contained the following:

The methylcyclohexanecarboxylic acids I (R = 1-, 2-, or 3-Me), prepared in 5 steps from the oxo esters II (R1 = Me, Et) via treatment with HOCMe2CN, dehydration, hydrogenation, hydrolysis, and reduction, were isomerized on treating with p-MeC6H4SO3H (III) followed by a weakly basic ion exchange resin. Thus, treating a mixture of cis- and trans-I (R = 1-Me) with III in H2O 1 h at room temperature gave cis-I (R = Me).4-MeC6H4SO3H which was eluted through Amberlite IR-45 (OH form) to give cis-I (R = Me). The experimental process involved the reaction of Methyl 1-methyl-4-oxocyclohexanecarboxylate(cas: 37480-41-4).COA of Formula: C9H14O3

The Article related to methylcyclohexanecarboxylic acid isomerization, aminomethylcyclohexanecarboxylic acid, cyclohexanecarboxylic acid aminomethyl, Alicyclic Compounds: Cyclohexanes and other aspects.COA of Formula: C9H14O3

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Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

On November 30, 1979, Isoda, Sumiro; Hirata, Miyoshi published an article.Reference of Methyl 1-methyl-4-oxocyclohexanecarboxylate The title of the article was Medicinal chemical studies on antiplasmin drugs. III. 4-Aminomethylcyclohexanecarboxylic acid and its derivatives having a methyl group. And the article contained the following:

The 1-, 4-, and α-Me derivatives of cis- and trans-4-(aminomethyl)cyclohexanecarboxylic acid (I) were prepared None of the products showed a more potent antiplasmin activity (no data) than trans-I. NMR studies showed that the CH2NH3 group has a conformational free energy ΔG° = -1.4 kcal/mol. Biol. active trans-I has both ring substituents in the equatorial positions, whereas cis-I exists mainly in the axial CH2N+H3-equatorial CO2- form. The experimental process involved the reaction of Methyl 1-methyl-4-oxocyclohexanecarboxylate(cas: 37480-41-4).Reference of Methyl 1-methyl-4-oxocyclohexanecarboxylate

The Article related to aminomethylcyclohexanecarboxylic acid preparation antiplasmin, conformation aminomethylcyclohexanecarboxylic acid, cyclohexanecarboxylic acid aminomethyl, Alicyclic Compounds: Cyclohexanes and other aspects.Reference of Methyl 1-methyl-4-oxocyclohexanecarboxylate

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

On May 26, 2021, Saito, Masato; Kawamata, Yu; Meanwell, Michael; Navratil, Rafael; Chiodi, Debora; Carlson, Ethan; Hu, Pengfei; Chen, Longrui; Udyavara, Sagar; Kingston, Cian; Tanwar, Mayank; Tyagi, Sameer; McKillican, Bruce P.; Gichinga, Moses G.; Schmidt, Michael A.; Eastgate, Martin D.; Lamberto, Massimiliano; He, Chi; Tang, Tianhua; Malapit, Christian A.; Sigman, Matthew S.; Minteer, Shelley D.; Neurock, Matthew; Baran, Phil S. published an article.Recommanded Product: Methyl 1-methyl-4-oxocyclohexanecarboxylate The title of the article was N-Ammonium Ylide Mediators for Electrochemical C-H Oxidation. And the article contained the following:

Herein, a rationally designed platform that provides a step toward this challenge using N-ammonium ylides e.g., acetamidotrimethylazanium-tetrafluoroboranuide as electrochem. driven oxidants for site-specific, chemoselective C(sp3)-H oxidn was presented. By taking a first-principles approach guided by computation, these new mediators were identified and rapidly expanded into a library using ubiquitous building blocks and trivial synthesis techniques. The ylide-based approach to C-H oxidation exhibits tunable selectivity that is often exclusive to this class of oxidants and can be applied to real-world problems in the agricultural and pharmaceutical sectors. The experimental process involved the reaction of Methyl 1-methyl-4-oxocyclohexanecarboxylate(cas: 37480-41-4).Recommanded Product: Methyl 1-methyl-4-oxocyclohexanecarboxylate

The Article related to ketone preparation regioselective chemoselective, aldehyde preparation regioselective chemoselective, hydrocarbon electrochem oxidation, ammonium ylide preparation, General Organic Chemistry: Synthetic Methods and other aspects.Recommanded Product: Methyl 1-methyl-4-oxocyclohexanecarboxylate

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Fraser, Robert R.; Raby, Bruce F. published an article in 1972, the title of the article was Substituent effect on geminal coupling constants in allylic methylene groups.Product Details of 37480-41-4 And the article contains the following content:

The geminal proton-proton coupling constants were determined for the allylic methylene protons in a series of selectively deuterated cyclohexene derivatives The effect of substituents β to the methylene group on 2J agrees with theoretical calculations Electron-withdrawing substituents cause a neg. shift and electron-donating substituents cause a pos. shift in 2J, the total variation being 2.9 Hz. This effect is larger than that exerted by para substituents in benzylic systems as would be expected for a more polarizable double bond. The 2J’s correlate poorly with the existing substituent parameters but correlate well with the shift of the olefinic protons adjacent to the double bond. This correlation is interpreted as evidence that the change in 2J is produced primarily by a resonance interaction of the substituent with the double bond resulting in a change in the hyperconjugative withdrawal of electrons from the adjacent methylene group. The experimental process involved the reaction of Methyl 1-methyl-4-oxocyclohexanecarboxylate(cas: 37480-41-4).Product Details of 37480-41-4

The Article related to substituent effect nmr allylic methylene, Physical Organic Chemistry: Spectral and Related Studies and other aspects.Product Details of 37480-41-4

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

On December 10, 2015, Kumaravel, Gnanasambandam; Peng, Hairuo; Xin, Zhili published a patent.Application In Synthesis of Methyl 1-methyl-4-oxocyclohexanecarboxylate The title of the patent was Preparation of dihydropyrazolopyridine derivatives for use as ATX modulators. And the patent contained the following:

Title compounds I [A = (un)substituted Ph, cyclohexyl, or heteroaryl; X = C(O), C(O)2, C(O)NH, or C(O)N(alkyl); Z = bond or alkylenyl; R2 = H, halo, CN, (un)substituted alkyl; R3 = CH3, CH3OCH3, (un)substituted carbocyclyl, etc.], and their pharmaceutically acceptable salts, are prepared and disclosed as ATX modulators. Thus, e.g., II was prepared by a multistep procedure (preparation given). I were evaluated in ATX activity assays, e.g., II demonstrated an IC50 value of no greater than 100 nM. The experimental process involved the reaction of Methyl 1-methyl-4-oxocyclohexanecarboxylate(cas: 37480-41-4).Application In Synthesis of Methyl 1-methyl-4-oxocyclohexanecarboxylate

The Article related to dihydropyrazolopyridine preparation atx modulator, Heterocyclic Compounds (More Than One Hetero Atom): Pyrazoles and other aspects.Application In Synthesis of Methyl 1-methyl-4-oxocyclohexanecarboxylate

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

On June 28, 2018, Liu, Phillip C.; Volgina, Alla; Wynn, Richard; Zolotarjova, Nina; Wu, Liangxing; Xiao, Kaijiong; Mei, Song; Lu, Liang; Zhu, Wenyu; Ye, Yingda; Wang, Haisheng; Qian, Ding-Quan; Yao, Wenqing published a patent.Computed Properties of 37480-41-4 The title of the patent was Synthesis of tetrahydroimidazo[4,5-c]pyridine derivatives as PD-L1 internalization inducers. And the patent contained the following:

Compositions of tetrahydroimidazo[4,5-c]pyridine derivatives I [Z = 5 to 14-membered heteroaryl, 4 to 14-membered heterocycloalkyl, C6-10 aryl, C3-10 cycloalkyl,m etc., L = bond, NH, O, C(O)NH, C(:NOH)NH, etc., R21, R22 = halo, C1-6 alkyl, CN, R23 = H, C1-6 alkyl, C1-6 haloalkyl, X = (R25)n, R25 = C1-4 alkyl, C1-4 alkoxy, C1-4 haloalkyl, etc., Y = (R26)m, R26 = C1-4 alkyl, CN, halo, OH, CO2H, etc., Z = (R27)p, R27 = H, halo, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, etc., n = 0-3, m = 0-3, p = 1-6, dotted bond = single or double bond to maintain the 5-membered imidazole ring aromaticity] and methods for inducing PD-L1 internalization are disclosed. The methods include reducing the amount of cell surface PD-L1 by contacting a cell expressing PD-L1 with a compound that binds to the cell surface PD-L1 and induces PD-L1 internalization. Compounds that induce PD-L1 internalization can be used to enhance, stimulate and/or increase an immune response and treat a PD-1-related disease or condition. The experimental process involved the reaction of Methyl 1-methyl-4-oxocyclohexanecarboxylate(cas: 37480-41-4).Computed Properties of 37480-41-4

The Article related to imidazopyridine preparation pd l1 internalization antitumor immunomodulator, Heterocyclic Compounds (More Than One Hetero Atom): Imidazoles and other aspects.Computed Properties of 37480-41-4

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

On January 16, 2014, Bentley, Jonathan Mark; Brookings, Daniel Christopher; Brown, Julien Alistair; Cain, Thomas Paul; Chovatia, Praful Tulshi; Foley, Anne Marie; Gallimore, Ellen Olivia; Gleave, Laura Jane; Heifetz, Alexander; Horsley, Helen Tracey; Hutchings, Martin Clive; Jackson, Victoria Elizabeth; Johnson, James Andrew; Johnstone, Craig; Kroeplien, Boris; Lecomte, Fabien Claude; Leigh, Deborah; Lowe, Martin Alexander; Madden, James; Porter, John Robert; Quincey, Joanna Rachel; Reed, Laura Claire; Reuberson, James Thomas; Richardson, Anthony John; Richardson, Sarah Emily; Selby, Matthew Duncan; Shaw, Michael Alan; Zhu, Zhaoning published a patent.Synthetic Route of 37480-41-4 The title of the patent was Imidazopyridine derivatives as modulators of TNF activity and their preparation. And the patent contained the following:

A series of imidazo[1,2-a]pyridine derivatives of formula I, being potent modulators of human TNFα activity, are accordingly of benefit in the treatment and/or prevention of various human ailments. Compounds of formula I wherein E is a bond, O, S, SO, SO2, etc.; Q is a bond, O, S, SO, SO2, NH and derivatives, etc.; Y is (un)substituted C3-7 cycloalkyl, (un)substituted aryl, (un)substituted heteroaryl, and (un)substituted C3-7 heterocyclyl; Z is H, halo, CF3, (un)substituted C1-6 alkyl, etc.; R1, R2, R3 and R4 are independently H, halo, CN, NO2, OH, etc.; and N-oxides, pharmaceutically acceptable salts, solvates, glucuronide derivatives and co-crystals thereof, are claimed. Example compound II was prepared by cyclocondensation of 5-(6-methoxypyridin-3-yl)pyridin-2-amine with acetaldehyde and 1,4-dichloro-2-isocyanobenzene. The invention compounds were evaluated for their TNFα modulatory activity. From the assay, it was determined that the tested example compounds all exhibited IC50 values of 50 μM or better. The experimental process involved the reaction of Methyl 1-methyl-4-oxocyclohexanecarboxylate(cas: 37480-41-4).Synthetic Route of 37480-41-4

The Article related to imidazopyridine preparation tnf modulator, Heterocyclic Compounds (More Than One Hetero Atom): Imidazoles and other aspects.Synthetic Route of 37480-41-4

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

On June 30, 1984, Sohda, Takashi; Meguro, Kanji; Kawamatsu, Yutaka published an article.Category: esters-buliding-blocks The title of the article was Studies on antidiabetic agents. IV. Synthesis and activity of the metabolites of 5-[4-(1-methylcyclohexylmethoxy)benzyl]-2,4-thiazolidinedione (ciglitazone). And the article contained the following:

5-[4-(1-Methylcyclohexylmethoxy)benzyl]-2,4-thiazolidinedione (ciglitazone) analogs I [RR1 = COCH2CH2, CH(OH)CH2CH2, CH2COCH2, CH2CH(OH)CH2, CH2CH2CO, CH2CH2CHOH] were synthesized to clarify the structure of the metabolites of I [RR1 = (CH2)3] and for studies of their pharmacol. properties. Of the metabolites identified, 5-[4-(t-3-hydroxy-1-methyl-r-1-cyclohexylmethoxy)benzyl]-2,4-thiazolidinedione exhibited extremely potent antidiabetic activity compared to I [RR1 = (CH2)3]. Stereoselective syntheses of 3- or 4-hydroxy-1-methylcyclohexanecarboxylic acids required for the preparation of 3′- or 4′-hydroxylated compounds are described. The experimental process involved the reaction of Methyl 1-methyl-4-oxocyclohexanecarboxylate(cas: 37480-41-4).Category: esters-buliding-blocks

The Article related to ciglitazone metabolite preparation, cyclohexylmethoxybenzylthiazolidinone oxo hydroxy, thiazolidinone cyclohexylmethoxybenzyl oxo hydroxy, Heterocyclic Compounds (More Than One Hetero Atom): Thiazoles, Isothiazoles and other aspects.Category: esters-buliding-blocks

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics