(E)-methyl 2-phenylpenta-2,4-dienoate | 1076238-94-2

• 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: (E)-methyl 2-phenylpenta-2,4-dienoate
• 英文别名: methyl 2-phenylpenta-2,4-dienoate；trans-Phenylpentadienoic acid methyl ester；methyl (2E)-2-phenylpenta-2,4-dienoate
• CAS: 1076238-94-2
• 化学式: C₁₂H₁₂O₂
• 分子量: 188.226
• InChiKey: CUISUHHWCVWKIB-YRNVUSSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  扁桃腈 在 盐酸 、 manganese(IV) oxide 、 三(二甲胺基)膦 作用下， 以 乙醚 、 二氯甲烷 、 乙腈 为溶剂， 反应 9.0h， 生成 (E)-methyl 2-phenylpenta-2,4-dienoate 、 (Z)-methyl 2-phenylpenta-2,4-dienoate
  参考文献：
  名称：

  P(NMe₂)₃-Mediated Umpolung Alkylation and Nonylidic Olefination of α-Keto Esters

  摘要：

  A commercial phosphorus-based reagent (P(NMe2)(3)) mediates,umpolung alkylation of methyl aroylformates with benzylic and allylic bromides, leading to either Barer-type addition or ylide-free olefination products upon workup. The reaction sequence is initiated, by a two-electron redox addition of the tricoordinate phosphorus reagent with an alpha-keto ester Compound (Kukhtin-Ramirez addition). A mechanistic rationale is offered for the chemoselectivity upon which the success of this nonmetal mediated C-C bond forming strategy is based.

  DOI：

  10.1021/acs.orglett.5b01784

文献信息

• Pd(0)-catalyzed cross-coupling of allyl halides with α-diazocarbonyl compounds or N-mesylhydrazones: synthesis of 1,3-diene compounds
  作者：Kang Wang、Shufeng Chen、Hang Zhang、Shuai Xu、Fei Ye、Yan Zhang、Jianbo Wang

  DOI：10.1039/c6ob00454g

  日期：——

  With palladium catalysis, allyl bromides or chlorides react with α-diazocarbonyl compounds or N-mesylhydrazones to afford 1,3-diene derivatives. The reaction represents a novel and efficient method for the synthesis of 1,3-butadiene derivatives. Mechanistically, the reaction is proposed to follow a pathway involving the formation of a π-allylic palladium carbene complex and subsequent migratory insertion

  在钯催化下，烯丙基溴或氯化物与α-重氮羰基化合物或N-甲磺酰基hydr反应生成1，3-二烯衍生物。该反应代表了一种新颖且有效的合成1,3-丁二烯衍生物的方法。从机理上讲，建议该反应遵循包括形成π-烯丙基钯卡宾配合物和随后的迁移插入的途径。
• Palladium-catalyzed reaction of allyl halides with α-diazocarbonyl compounds
  作者：Shufeng Chen、Jianbo Wang

  DOI：10.1039/b806970k

  日期：——

  The Pd(OAc)(2)-catalyzed reaction between alpha-diazocarbonyl compounds and allyl bromides or chlorides leads to the formation of 1,3-diene derivatives.

  α-重氮羰基化合物与烯丙基溴或氯化物之间的Pd（OAc）（2）催化反应导致形成1,3-二烯衍生物。
• Cyclopropylmethyl Palladium Species from Carbene Migratory Insertion: New Routes to 1,3-Butadienes
  作者：Lei Zhou、Fei Ye、Yan Zhang、Jianbo Wang

  DOI：10.1021/ol2034405

  日期：2012.2.3

  Cyclopropylmethyl palladium species can be accessed by Pd-catalyzed reaction of either cyclopropyl N-tosylhydrazone with halide or N-tosylhydrazone with cyclopropyl halide. In both approaches migratory insertion of Pd carbene is the key process. These transformations constitute new approaches toward 1,3-butadiene derivatives.

  环丙基甲基钯物质可通过环丙基N-甲苯磺酰to与卤化物或N-甲苯磺酰with与环丙基卤化物的Pd催化反应获得。在这两种方法中，Pd卡宾的迁移插入都是关键过程。这些转变构成了针对1,3-丁二烯衍生物的新方法。