[(E)-1-cyano-2-methyl-3-phenylprop-2-enyl] ethyl carbonate | 1346232-37-8

• 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)-1-cyano-2-methyl-3-phenylprop-2-enyl] ethyl carbonate
• CAS: 1346232-37-8
• 化学式: C₁₄H₁₅NO₃
• 分子量: 245.278
• InChiKey: XMIUCSPRNORKFE-PKNBQFBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  59.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(E)-1-cyano-2-methyl-3-phenylprop-2-enyl] ethyl carbonate 、 ethyl 2-((tert-butoxycarbonyloxy)methyl)acrylate 在 三乙烯二胺 、 二碳酸二叔丁酯 作用下， 以 乙腈 为溶剂， 反应 15.0h， 以73%的产率得到
  参考文献：
  名称：

  Construction of Highly Functional Quaternary Carbon Stereocenters via an Organocatalytic Tandem Cyanation–Allylic Alkylation Reaction

  摘要：

  The first tertiary amine-catalyzed tandem cyanation-allyic alkylation (CAA) reaction of aldehydes, appropriate cyanide sources, and Morita-Baylis-Hillman (MBH) adducts has been developed, which provides a facile access to densely functionalized products containing O-substituted quaternary centers.

  DOI：

  10.1021/ol202499g
• 作为产物：
  描述：

  氰基甲酸乙酯 、 反式-alpha-甲基肉桂醛 在 4-二甲氨基吡啶 作用下， 反应 1.08h， 以92%的产率得到[(E)-1-cyano-2-methyl-3-phenylprop-2-enyl] ethyl carbonate
  参考文献：
  名称：

  N,N-Dimethylpyridin-4-Amine Mediated Protocol for Cyanoethoxycarbonylation of Aldehydes Under Solvent-Free Conditions

  摘要：

  N, N-Dimethylpyridin-4-amine (DAMP) (10 mol%) was successfully employed as catalyst for cyanoethoxycarbonylation of aromatic and aliphatic aldehydes at room temperature under solvent free condition to give corresponding ethylcyanocarbonates in excellent isolated yield (up to 95%) in 15-90 min. Simple experimental conditions and product isolation procedure has made this protocol quite attractive for the synthesis of ethylcyanocarbonates in an environment-friendly manner.

  DOI：

  10.1007/s10562-010-0355-7

文献信息

• Construction of Highly Functional Quaternary Carbon Stereocenters <i>via</i> an Organocatalytic Tandem Cyanation–Allylic Alkylation Reaction
  作者：Zhe Zhuang、Feng Pan、Jian-Guo Fu、Jian-Ming Chen、Wei-Wei Liao

  DOI：10.1021/ol202499g

  日期：2011.12.2

  The first tertiary amine-catalyzed tandem cyanation-allyic alkylation (CAA) reaction of aldehydes, appropriate cyanide sources, and Morita-Baylis-Hillman (MBH) adducts has been developed, which provides a facile access to densely functionalized products containing O-substituted quaternary centers.
• Lewis Base Promoted Intramolecular Acylcyanation of α-Substituted Activated Alkenes: Construction of Ketones Bearing β-Quaternary Carbon Centers
  作者：Zhe Zhuang、Jian-Ming Chen、Feng Pan、Wei-Wei Liao

  DOI：10.1021/ol3007716

  日期：2012.5.4

  A novel phosphine-promoted intramolecular acylcyanation of alpha-substituted activated alkenes has been developed, which provides a unique access to densely functionalized acyclic ketones bearing beta-quaternary carbon centers with a remarkable feature that both alpha- and beta-positions of activated alkene are functionalized.
• N,N-Dimethylpyridin-4-Amine Mediated Protocol for Cyanoethoxycarbonylation of Aldehydes Under Solvent-Free Conditions
  作者：Noor-ul H. Khan、Santosh Agrawal、Rukhsana I. Kureshy、Prasanta K. Bera、Sayed H. R. Abdi、Hari C. Bajaj

  DOI：10.1007/s10562-010-0355-7

  日期：2010.7

  N, N-Dimethylpyridin-4-amine (DAMP) (10 mol%) was successfully employed as catalyst for cyanoethoxycarbonylation of aromatic and aliphatic aldehydes at room temperature under solvent free condition to give corresponding ethylcyanocarbonates in excellent isolated yield (up to 95%) in 15-90 min. Simple experimental conditions and product isolation procedure has made this protocol quite attractive for the synthesis of ethylcyanocarbonates in an environment-friendly manner.