3-Methyl-2-phenyl-2-butenal | 55106-21-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-Methyl-2-phenyl-2-butenal
• 英文别名: 3-Methyl-2-phenylbut-2-enal
• CAS: 55106-21-3
• 化学式: C₁₁H₁₂O
• 分子量: 160.216
• InChiKey: BKBMAPYNGONVFY-UHFFFAOYSA-N

物化性质

• 沸点：
  271.9±19.0 °C(Predicted)
• 密度：
  0.977±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-Methyl-2-phenyl-2-butenal 在 manganese(IV) oxide 、 正丁基锂 、 三苯基甲烷 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 24.25h， 生成 2-Methyl-3-phenyl-2-hepten-5-yn-4-one
  参考文献：
  名称：

  Enynones in Organic Synthesis. 7. Substituent Effects on the .alpha.-Tocopherol-Catalyzed Cyclization of Enynones to Methylenecyclopentenones. Convenient Syntheses of Members of the Methylenomycin Class of Antibiotics

  摘要：

  Substituent effects on the a-tocopherol (vitamin E, 3b) catalyzed cyclization of a wide variety of enynones 1a-z to methylenecyclopentenones 7a-z have been examined, with particular emphasis given to electron-withdrawing and -donating groups at positions 2-4 and 6. In general, electron-withdrawing groups at positions 4 and 6 dramatically accelerate the cyclization process, while strong electron-donating groups at positions 3 and 4 completely inhibit reaction. Relatively little effect is exerted by groups at C-2, except for the methyl ester derivative 1i, which is totally unreactive. This methodology was employed in the syntheses of the methylenecyclopentenone antibiotics methylenomycin B (7a) and desepoxy-4,5-didehydromethylenomycin A (7z) and in formal syntheses of methylenomycin A (8) and xanthocidin (9).

  DOI：

  10.1021/jo00097a036
• 作为产物：
  描述：

  3-methyl-2-phenylbutanoyl chloride 在 palladium on barium sulfate 磺酰氯 、 氢气 、 lithium perchlorate 、 calcium carbonate 作用下， 以 六甲基磷酰三胺 、 二氯甲烷 、 xylene 为溶剂， 生成 3-Methyl-2-phenyl-2-butenal
  参考文献：
  名称：

  Duhamel,L.; Gralak,J., Bulletin de la Societe Chimique de France, 1974, p. 2124 - 2128

  摘要：

  DOI：

文献信息

• Heck Arylation of α,β-Unsaturated Aldehydes
  作者：A. Nejjar、C. Pinel、L. Djakovitch

  DOI：10.1002/adsc.200202180

  日期：2003.5

  The Heck arylation of α,β-unsaturated aldehydes is strongly dependent on the catalyst, the solvent and the base. Optimized conditions yielded either selectively cinnamyl derivatives (83%) or double arylation products (88% based on aryl conversion). A new α-arylation of β,β-disubstituted acrolein is also realized.

  α，β-不饱和醛的Heck芳基化在很大程度上取决于催化剂，溶剂和碱。优化的条件产生选择性的肉桂基衍生物（83％）或双芳基化产物（基于芳基转化率88％）。还实现了β，β-二取代的丙烯醛的新的α-芳基化。
• PROCESS FOR PRODUCING ALPHA, BETA-UNSATURATED ALDEHYDE COMPOUNDS
  申请人：Ishida Kosaku

  公开号：US20090171124A1

  公开（公告）日：2009-07-02

  The present invention relates to processes for producing α,β-unsaturated aldehyde compounds and unsaturated alcohols with a good yield. There is provided a process for producing and α,β-unsaturated aldehyde compound including the step of subjecting a raw aldehyde compound to an intermolecular condensation reaction in the presence of an amine and a protonic acid having 4 to 20 carbon atoms or a salt thereof; and a process for producing an unsaturated alcohol including the step of subjecting the α,β-unsaturated aldehyde compound to a reduction reaction.

  本发明涉及一种生产α，β-不饱和醛化合物和不饱和醇的工艺，其产率高。提供了一种生产α，β-不饱和醛化合物的工艺，包括在胺和具有4到20个碳原子的质子酸或其盐的存在下，使原始醛化合物经历一种分子间缩合反应的步骤；以及一种生产不饱和醇的工艺，包括使α，β-不饱和醛化合物经历还原反应的步骤。
• Stereochemistry of Carbenic 1,2-Vinyl Shifts
  作者：Wolfgang Kirmse、Siegfried Kopannia

  DOI：10.1021/jo971691t

  日期：1998.2.1

  Various 1-phenylbut-3-enylidenes, (Ph)CCR2CH=CHR', were generated thermally and photolytically from tosylhydrazone (diazo) precursors. 1,2-Vinyl shifts, leading to 1,3-dienes, R'CH=CHC(Ph)=CR2, were found to predominate over gamma-C-H insertion (R = Me) and to compete with 1,2-H shifts (R = H). Intramolecular addition to the double bond was detected in the case of R = R' = Me. The resulting bicyclobutane is thermally stable and does not mediate the vinyl shift. Stereospecific migration of 1-propenyl groups (R' = Me), with retention of configuration, was observed on thermolysis and direct photolysis of appropriate substrates. These data exclude the intervention of a triplet diradical and point, to vinyl migration in the singlet manifold. Benzophenone-sensitized generation of the carbenes led to partial stereomutation but did not provide conclusive evidence for a triplet rearrangement (isomerization of the diene products could not be avoided under these conditions).
• Dana,G. et al., Bulletin de la Societe Chimique de France, 1976, p. 2063 - 2067
  作者：Dana,G. et al.

  DOI：——

  日期：——
• A Domino Process toward Functionally Dense Quaternary Carbons through Pd-Catalyzed Decarboxylative C(sp³)–C(sp³) Bond Formation
  作者：Wusheng Guo、Rositha Kuniyil、José Enrique Gómez、Feliu Maseras、Arjan W. Kleij

  DOI：10.1021/jacs.7b12608

  日期：2018.3.21

  An efficient protocol was developed to construct functionally dense quaternary carbons with concomitant formation of a new Csp(3)-Csp(3) bond via Pd-catalyzed decarboxylative transformation of vinyl cyclic carbonates. This redox-neutral catalytic system features stereocontrolled formation of multisubstituted allylic scaffolds with an aldehyde functionality generated in situ, and it typically can be performed at room temperature without any additives. DFT calculations provide a rationale toward the selective formation of these compounds and reveal a complex mechanism that with the help of microkinetic models is able to reproduce the nontrivial dependence of the identity of the product on the nature of the substituents in the substrate.