Prop-2-enyl 2-benzyl-2-cyano-3-phenylpropanoate | 1199790-57-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: Prop-2-enyl 2-benzyl-2-cyano-3-phenylpropanoate
• 英文别名: prop-2-enyl 2-benzyl-2-cyano-3-phenylpropanoate
• CAS: 1199790-57-2
• 化学式: C₂₀H₁₉NO₂
• 分子量: 305.376
• InChiKey: TWUZBKKELCDRCS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Prop-2-enyl 2-benzyl-2-cyano-3-phenylpropanoate 在 四(三苯基膦)钯 作用下， 以 甲苯 为溶剂， 生成 2-苄基-3-苯基丙腈
  参考文献：
  名称：

  Regiospecific Decarboxylative Allylation of Nitriles

  摘要：

  Palladium-catalyzed decarboxylative alpha-allylation of nitriles readily occurs with use of Pd-2(dba)(3) and rac-BINAP. This catalyst mixture also allows the highly regiospecific alpha-allylation of nitrites in the presence of much more acidic (x-protons. Thus, the reported method provides access to compounds that are not readily available via base-mediated allylation chemistries. Lastly, mechanistic investigations indicate that there is a competition between C- and N-allylation of an intermediate nitrile-stabilized anion and that N-allylation is followed by a rapid [3,3]-sigmatropic rearrangement.

  DOI：

  10.1021/ol902065p
• 作为产物：
  描述：

  氰乙酸烯丙酯 、 溴甲苯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 Prop-2-enyl 2-benzyl-2-cyano-3-phenylpropanoate
  参考文献：
  名称：

  催化硝酸盐实现的钯催化烯烃有氧分子内氨基乙酰氧基化

  摘要：

  以分子氧为氧化剂，实现了一种温和需氧分子内氨基乙酰氧基化合成吡咯烷和二氢吲哚衍生物的方法。催化NO x物质充当电子转移介体，以获取高价钯中间体作为假定的活性氧化剂。

  DOI：

  10.1021/acs.orglett.6b02722

文献信息

• Palladium-Catalyzed Aerobic Intramolecular Aminoacetoxylation of Alkenes Enabled by Catalytic Nitrate
  作者：Jiaming Li、Robert H. Grubbs、Brian M. Stoltz

  DOI：10.1021/acs.orglett.6b02722

  日期：2016.11.4

  A mild aerobic intramolecular aminoacetoxylation method for the synthesis of pyrrolidine and indoline derivatives was achieved using molecular oxygen as the oxidant. A catalytic NOx species acts as an electron transfer mediator to access a high-valent palladium intermediate as the presumed active oxidant.

  以分子氧为氧化剂，实现了一种温和需氧分子内氨基乙酰氧基化合成吡咯烷和二氢吲哚衍生物的方法。催化NO x物质充当电子转移介体，以获取高价钯中间体作为假定的活性氧化剂。
• Regiospecific Decarboxylative Allylation of Nitriles
  作者：Antonio Recio、Jon A. Tunge

  DOI：10.1021/ol902065p

  日期：2009.12.17

  Palladium-catalyzed decarboxylative alpha-allylation of nitriles readily occurs with use of Pd-2(dba)(3) and rac-BINAP. This catalyst mixture also allows the highly regiospecific alpha-allylation of nitrites in the presence of much more acidic (x-protons. Thus, the reported method provides access to compounds that are not readily available via base-mediated allylation chemistries. Lastly, mechanistic investigations indicate that there is a competition between C- and N-allylation of an intermediate nitrile-stabilized anion and that N-allylation is followed by a rapid [3,3]-sigmatropic rearrangement.