Category: 5205-11-8

Yasui, Kengo published the artcileUnsymmetrical Ketone Synthesis via a Three-Component Connection Reaction of Organozincs, Allylating Agents, and Carbon Monoxide, Name: 3-Methylbut-2-en-1-yl benzoate, the publication is Journal of Organic Chemistry (1995), 60(5), 1365-80, database is CAplus.

A wide variety of organozincs [diethylzinc, alkylzinc halides, IZn(CH₂)_nCO₂Et [n = 2, 3 (5)], and IZn(CH₂)_nCN (n = 2-6)] undergo a three-component connection reaction with carbon monoxide and allylic benzoates or phosphates to furnish unsym. ketones in good yields under 1 atm of carbon monoxide at ambient temperature by catalysis of tetrakis(triphenylphosphine)palladium in THF/HMPA. The regio- and stereoselectivities of the carbonylation show marked contrast to those reported for the palladium-catalyzed carbonylation of unsym. allylic substrates. For example, the reaction of crotyl benzoate with octylzinc iodide provides all the possible stereo- and regioisomers, i.e., cis- and trans-2-butenyl and 1-methyl-2-propenyl octyl ketones in comparable amounts The carbonylative coupling of trans- and cis-carvyl di-Et phosphates and 5 is stereospecific and proceeds with inversion of configuration at the allylic stereocenters to furnish cis- and trans-carvyl γ-(ethoxycarbonyl)propyl ketone, resp., as single diastereomers. In the absence of HMPA, the reaction feature changes dramatically and lactones and sym. keto diesters are formed in varying ratios depending on the reaction conditions. The synthetic scope of the unsym. ketones and mechanistic rationale for these unique and unprecedented reaction behaviors are discussed.

Journal of Organic Chemistry published new progress about 5205-11-8. 5205-11-8 belongs to esters-buliding-blocks, auxiliary class Alkenyl,Benzene,Ester, name is 3-Methylbut-2-en-1-yl benzoate, and the molecular formula is C9H9BN2O3, Name: 3-Methylbut-2-en-1-yl benzoate.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Lu, Lingxiang published the artcileThree-Component Chlorophosphinoylation of Alkenes via Anodically Coupled Electrolysis, Name: 3-Methylbut-2-en-1-yl benzoate, the publication is Synlett (2019), 30(10), 1199-1203, database is CAplus.

Authors report the development of an electrocatalytic protocol for the chlorophosphinoylation of simple alkenes. Driven by electricity and mediated by a Mn catalyst, the heterodifunctionalization reaction takes place with high efficiency and regioselectivity. Cyclic voltammetry data are consistent with a mechanistic scenario based on anodically coupled electrolysis in which the generation of two distinct radical intermediates occur simultaneously on the anode and are both mediated by the Mn catalyst.

Synlett published new progress about 5205-11-8. 5205-11-8 belongs to esters-buliding-blocks, auxiliary class Alkenyl,Benzene,Ester, name is 3-Methylbut-2-en-1-yl benzoate, and the molecular formula is C12H14O2, Name: 3-Methylbut-2-en-1-yl benzoate.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Andreev, V. M. published the artcileThe synthesis of esters of 2-methyl-2-buten-4-ol (prenol) and 2-methyl-1-buten-4-ol (isobutenyl carbinol), Recommanded Product: 3-Methylbut-2-en-1-yl benzoate, the publication is Pishchevaya Promyshlennost (Moscow, Russian Federation) (1992), 22, database is CAplus.

Perfumes RCO₂R’ (RCO₂ = benzoate, cinnamate, salicylate, isobutyrate, phenylacetate, phenoxyacetate, nicotinate; R’ = prenyl, isobutenylcarbinyl) were prepared in ≤79% yield in the K₂CO₃-catalyzed transesterification of RCO₂Me with R’OH. The odors were evaluated.

Pishchevaya Promyshlennost (Moscow, Russian Federation) published new progress about 5205-11-8. 5205-11-8 belongs to esters-buliding-blocks, auxiliary class Alkenyl,Benzene,Ester, name is 3-Methylbut-2-en-1-yl benzoate, and the molecular formula is C12H14O2, Recommanded Product: 3-Methylbut-2-en-1-yl benzoate.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Brokl, Michal published the artcileImprovement of ylang-ylang essential oil characterization by GC × GC-TOFMS, Product Details of C12H14O2, the publication is Molecules (2013), 1783-1797, database is CAplus and MEDLINE.

A single fraction of essential oil can often contain hundreds of compounds Despite of the tech. improvements and the enhanced selectivity currently offered by the state-of-the-art gas chromatog. (GC) and mass spectrometry (MS) instruments, the complexity of essential oils is frequently underestimated. Comprehensive two-dimensional GC coupled to time-of-flight MS (GC × GC-TOFMS) was used to improve the chem. characterization of ylang-ylang essential oil fractions recently reported in a previous one-dimensional (1D) GC study. Based on both, the enhanced chromatog. separation and the mass spectral deconvolution, 161 individual compounds were identified and labeled as potentially characteristic analytes found in both low and high boiling fractions issued from distillation of mature ylang-ylang flowers. Compared to the most recent full GC-MS characterization, this represents 75 new compounds, essentially consisting of terpenes, terpenoid esters, and alcs.

Molecules published new progress about 5205-11-8. 5205-11-8 belongs to esters-buliding-blocks, auxiliary class Alkenyl,Benzene,Ester, name is 3-Methylbut-2-en-1-yl benzoate, and the molecular formula is C12H14O2, Product Details of C12H14O2.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Sipes, I. G. published the artcileBenzyl derivatives, Product Details of C12H14O2, the publication is WHO Food Additives Series (2011), 189-206, database is CAplus.

The Committee evaluated eight addnl. flavoring agents belonging to the group of benzyl derivatives that was previously evaluated. The structural feature common to all members of the group is a primary oxygenated functional group bonded directly to a benzene ring or a functional group metabolized to a benzyl alc. or benzoic acid derivative Generally, the Committee concluded that these eight flavoring agents, which are additions to the group of benzyl derivatives evaluated previously, would not give rise to safety concerns at current estimated dietary exposures.

WHO Food Additives Series published new progress about 5205-11-8. 5205-11-8 belongs to esters-buliding-blocks, auxiliary class Alkenyl,Benzene,Ester, name is 3-Methylbut-2-en-1-yl benzoate, and the molecular formula is C20H12N2O2, Product Details of C12H14O2.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Sun, Ye-zhi published the artcileStudy on the quantitative structure-toxicity relationships of benzoic acid derivatives in rats via oral LD₅₀, Application of 3-Methylbut-2-en-1-yl benzoate, the publication is Medicinal Chemistry Research (2009), 18(9), 712-724, database is CAplus.

Quant. structure-toxicity relationship (QSTR) studies play an important role in toxicity forecasting, which is widely used in the study of modern compounds Benzoic acid derivatives are an important type of organic chems. Most of them may cause serious public health and environmental problems. The effect of quantum-chem. parameters on the toxicity of benzoic acid derivatives in rats via oral 50% LD (LD₅₀) was studied by QSTR, and a model to predict the toxicity of benzoic acid derivatives was constructed. In order to obtain an accurate model, cross factors were considered and a model for predicting the toxicity of benzoic acid derivatives in rats via oral LD₅₀ was built using a linear regression method (correlation 0.990). The novel model is -log^toxi = 0.144 LogP -0.0269SAG + 0.0000127HoF – 0.000377PE, R² = 0.990, C(p) = 4.000, mean square error (MSE) = 0.785. The model demonstrated good forecasting ability.

Medicinal Chemistry Research published new progress about 5205-11-8. 5205-11-8 belongs to esters-buliding-blocks, auxiliary class Alkenyl,Benzene,Ester, name is 3-Methylbut-2-en-1-yl benzoate, and the molecular formula is C10H13NO2, Application of 3-Methylbut-2-en-1-yl benzoate.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Ramnauth, Jailall published the artcilePhotochemical preparation of cyclopropanes from cyclobutanones, Formula: C12H14O2, the publication is Canadian Journal of Chemistry (2001), 79(2), 114-120, database is CAplus.

A general method for the preparation of cyclopropanes is reported. Triplet-photosensitized reactions of cyclobutanones give cyclopropanes as the major product. Part 1 describes the synthesis of substituted cyclobutanones used. In Part 2, the photo-reactions of cyclobutanones are reported. Triplet-sensitized reactions of cyclobutanones using acetone as a sensitizer give cyclopropanes as the major nonpolar products. The extent of photodecarbonylation seems to be dependent on α-substitution. Electron-donating groups promote decarbonylation while electron-withdrawing groups favor cycloelimination.

Canadian Journal of Chemistry published new progress about 5205-11-8. 5205-11-8 belongs to esters-buliding-blocks, auxiliary class Alkenyl,Benzene,Ester, name is 3-Methylbut-2-en-1-yl benzoate, and the molecular formula is C12H14O2, Formula: C12H14O2.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Maguet, Louis published the artcileEsterification of 3-methyl-1,3-butanediol, Category: esters-buliding-blocks, the publication is Bulletin de la Societe Chimique de France (1965), 3262-6, database is CAplus.

A method is described for the diesterification of Me₂C(OH)CH₂CH₂OH (I) by organic acid anhydrides without the dehydration of the tertiary OH. I was also converted to the corresponding Me₂C(OH)CH₂CH₂O₂CR (II) and Me₂C:CHCH₂O₂CR (III) and(or) CH₂:CMeCH₂CH₂O₂CR (IV). I (104 g.) and 102 g. Ac₂O kept 1 hr. slightly below 70° and heated 1 hr. at 147° yielded 94% II (R = Me) (V), b₂₀ 105°, n²⁰_D 1.4300, d₂₅ 0.9993. I (38 g.) and 81 g. (C₆H₁₃CO)₂O (VI) in 63 g. MePh refluxed 6 hrs. gave 87% II (R = C₆H₁₃) (VII), b_0.15 87-93°, n²⁰_D 1.4412. I (114 g.), 150 cc. C₆H₆, and 110 g. Na₂CO₃ treated during 2 hrs. at 60° with 148 g. C₆H₁₃COCI (VIIa) and heated 2 hrs. at 60-70° yielded 137 g. VII, b_0.60 105°, n²⁰_D 1.4411, d₂₅ 0.9336. I with BzCl gave similarly during 4 hrs. 68% II (R = Ph) (VIII), b_0.9 127-8°, n²_D⁰ 1.5138, d₂₅ 1.0762. I (156 g.), 142 g. C₁₇H₃₅CO₂H, 77 cc. xylene, and 3 g. Al₂O₃ refluxed 17 hrs. with the azeotropic removal of H₂O yielded 116 g. II (R = C₁₇H₃₅), m. 40° (heptane). C₈H₁₇CH:CH(CH₂)₇CO₂Me (169 g.) and 119 g. I distilled to remove 10 cc. I, treated with a piece of K, heated to 180° with the overhead removal of the MeOH, treated with 0.8 g. K in small pieces at intervals during 5 hrs., and distilled gave 70% II [R = C₈H₁₇CH:CH(CH₂)₇], b_0.03 178-85°, n²⁰_D 1.4623, d₂₅ 0.9045. I (86 g.) added dropwise during 15 min. to 132.6 g. refluxing Ac₂O yielded 115 g. IV (R = Me) (IX), b₇₆₀ 143-5°, n²⁰_D 1.4212, d₂₅ 0.9137. I (104 g.), 71 g. AcOH, 150 cc. C₆H₆, and 1 g. PhSO₃H refluxed 5 hrs. with the azeotropic removal of H₂O yielded 74 g. mixture, b₄₀ 63-72°, of 80% IX and 20% III (R = Me) (X). V (22.2 g.) in 50 cc. MePh refluxed with 1% iodine gave isoprene and only 30% mixture of IX and X; a similar run in C₆H₆ with C₁₀H₇SO₃H yielded 50% mixture of 85% IX and 15% X. C₆H₁₃CO₂H (65 g.), 57 g. I, 135 cc. C₆H₆, and 0.6 g. C₁₀H₇SO₃H gave similarly 49 g. 80:20 mixture of IV (R = C₆H₁₃) (XI) and III (R = C₆H₁₃) (XII), b_1.7 84-87°, n²⁰_D 1.4378, d₂₅ 0.879, and 18g. 65:35 mixture of XI and XII, b_1.787-95°. BzOH (183 g.), 172 g. I, 300 cc. C₆H₆, and 1 g. PhSO₃H refluxed 13 hrs. yielded after 11 g. forerun, b_0.2 45-56°, n²⁰_D 1.4608, 34.5 g. mixture, b_0.2 60-4°, n²⁰_D 1.5093, d₂₅ 1.0125, of IV (R = Ph) (XIII) and III (R = Ph) (XIV) containing mostly XIII, and 24 g. mixture, b_0.2 64-5°, n_20D 1.5118, of XIII and XIV containing mostly XIV. CH₂: CMeCH₂CH₂OH (35 g.), 50 cc. CHCl₃, and 29 g. C₅H₅N treated dropwise during 2 hrs. with 101 g. C₁₇H₃₅COCl in 100 cc. CHCl₃ at 30-40° and refluxed 2 hrs. yielded 95 g. IV (R = C₁₇H₃₅), n²⁰_D 1.4518, d₂₀ 0.8670. Similarly was prepared from oleyl chloride 71% IV [R = C₈H₁₇CH:CH(CH₂)₇], b_0.01 150-65°, n²⁰_D 1.4605, d₂₀ 0.8765. Ac₂O (1326 g.) treated at reflux with 520 g. I yielded 797 g. Me₂C (O₂CR)CH₂CH₂O₂CR’ (XV) (R = R’ = Me), b₁₉ 108-9°, n²⁰_D 1.4247, d₂₅ 1.0189, and a small amount of a mixture of 63% IX and 37% X. I (26 g.), 156 g. VI, and 80 g. MePh refluxed 13 hrs. yielded 61.5 g. XV (R = R’ = C₆H₁₃) (XVI), b_0.1 128-34°, n²⁰_D 1.4418. I (36.4 g.) in 150 cc. CHCl₃ and 100 cc. C₅H₅N treated dropwise with stirring during 3 hrs. with 119 g. VIIa at 30° and heated 5 hrs. at 60° yielded 100 g. XVI, b_0.15 130-5°, n²⁰_D 1.4418, d₂₅ 0.9256. I (47 g.) with 135 g. BzCl gave similarly 31 g. distillate, b. 120-2°, containing mostly VIII and 82 g. XV (R = R’ = Ph), m. 34° (AmOH), d₂₅ 1.1212. VIII (104 g.) and 67 g. Ac₂O heated 5 hrs. at 140° yielded 112 g. XV (R = Me, R’ = Ph), b_0.85 131-2°, n²⁰_D 1.4974, d₂₅ 1.0820. Similarly were prepared the following XV (R = Me) (R’, % yield, b.p./mm. or m.p., n²⁰_D, and d₂₀ given): C₆H₁₃, 94, 109-10°/0.6, 1.4360, 0.95874; C₈H₁₇CH:CH(CH₂)₇, 95, –, 1.4582, 0.92084; C₁₇H₃₅, 98, 24-5°, –, –.

Bulletin de la Societe Chimique de France published new progress about 5205-11-8. 5205-11-8 belongs to esters-buliding-blocks, auxiliary class Alkenyl,Benzene,Ester, name is 3-Methylbut-2-en-1-yl benzoate, and the molecular formula is C12H14O2, Category: esters-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Bychek, Roman M. published the artcileSynthesis of Functionalized Difluorocyclopropanes: Unique Building Blocks for Drug Discovery, Computed Properties of 5205-11-8, the publication is Chemistry – A European Journal (2018), 24(47), 12291-12297, database is CAplus and MEDLINE.

Difluorocyclopropane-containing building blocks for drug discovery were synthesized from the functionalized alkenes and TMSCF₃/NaI. Novel fluorinated acids, amines, amino acids, alcs., ketones and sulfonyl chlorides were obtained.

Chemistry – A European Journal published new progress about 5205-11-8. 5205-11-8 belongs to esters-buliding-blocks, auxiliary class Alkenyl,Benzene,Ester, name is 3-Methylbut-2-en-1-yl benzoate, and the molecular formula is C12H14O2, Computed Properties of 5205-11-8.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Chi, Ki Whan published the artcileA substituent effect on the palladium(II) catalyzed [3,3]-sigmatropic rearrangement of allylic esters, Safety of 3-Methylbut-2-en-1-yl benzoate, the publication is Bulletin of the Korean Chemical Society (1994), 15(2), 98-100, database is CAplus.

To a solution of I( X=p-MeO,p-Me,p-Cl,m-CF₃,p-NO₂, etc.) in THF at 25° was added bis(acetonitrile)palladium(II) chloride catalysts to yield II(X as above) in more than 97% GC yield. Pseudo-first-order rate constants(k_p) were obtained by least-square method from the slope of substrate concentration vs. time; the second-order rate constants(k₂) were then calculated from a division of k_p by the concentration of catalysts. A Hammett plot of k₂ vs. σ shows a good linear correlation (s=0.977) and retardation of the reaction rate is directly proportional to the strength of electron-withdrawing ability of the substituents (ρ= -1.05). A cyclization-induced mechanism was postulated. Since the rate decreases proportional to σ, the rate-determining step is the second step in which the pos.-charged intermediate is produced,. The small absolute value of ρ is attributed to the delocalization of pos. charge over the neighboring oxygen atoms in the transition state.

Bulletin of the Korean Chemical Society published new progress about 5205-11-8. 5205-11-8 belongs to esters-buliding-blocks, auxiliary class Alkenyl,Benzene,Ester, name is 3-Methylbut-2-en-1-yl benzoate, and the molecular formula is C12H14O2, Safety of 3-Methylbut-2-en-1-yl benzoate.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics