Methyl 4-(4-chlorophenyl)-4-cyano-4-ethoxycarbonyloxy-2-methylidenebutanoate | 1346231-85-3

• 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: Methyl 4-(4-chlorophenyl)-4-cyano-4-ethoxycarbonyloxy-2-methylidenebutanoate
• 英文别名: methyl 4-(4-chlorophenyl)-4-cyano-4-ethoxycarbonyloxy-2-methylidenebutanoate
• CAS: 1346231-85-3
• 化学式: C₁₆H₁₆ClNO₅
• 分子量: 337.76
• InChiKey: OGOIWMDWGJAPDW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  85.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Methyl 4-(4-chlorophenyl)-4-cyano-4-ethoxycarbonyloxy-2-methylidenebutanoate 在 二乙基苯膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以70%的产率得到1-ethyl 3-methyl 2-(2-(4-chlorophenyl)-2-oxoethyl)-2-(cyanomethyl)malonate
  参考文献：
  名称：

  Lewis Base Promoted Intramolecular Acylcyanation of α-Substituted Activated Alkenes: Construction of Ketones Bearing β-Quaternary Carbon Centers

  摘要：

  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.

  DOI：

  10.1021/ol3007716
• 作为产物：
  描述：

  methyl 2-(((tert-butoxycarbonyl)oxy)methyl)acrylate 、 cyano(4-chlorophenyl)methyl ethyl carbonate 在 三乙烯二胺 作用下， 以 乙腈 为溶剂， 生成 Methyl 4-(4-chlorophenyl)-4-cyano-4-ethoxycarbonyloxy-2-methylidenebutanoate
  参考文献：
  名称：

  Lewis Base Promoted Intramolecular Acylcyanation of α-Substituted Activated Alkenes: Construction of Ketones Bearing β-Quaternary Carbon Centers

  摘要：

  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.

  DOI：

  10.1021/ol3007716

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.