Methyl 4-cyano-4-ethoxycarbonyloxy-4-(2-methoxyphenyl)-2-methylidenebutanoate | 1346231-94-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: Methyl 4-cyano-4-ethoxycarbonyloxy-4-(2-methoxyphenyl)-2-methylidenebutanoate
• CAS: 1346231-94-4
• 化学式: C₁₇H₁₉NO₆
• 分子量: 333.341
• InChiKey: QTASBRSTKBMWNS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  94.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Methyl 4-cyano-4-ethoxycarbonyloxy-4-(2-methoxyphenyl)-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87%的产率得到1-ethyl 3-methyl 2-(cyanomethyl)-2-(2-(2-methoxyphenyl)-2-oxoethyl)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 、 [氰基-(2-甲氧基苯基)甲基]碳酸乙酯 在 三乙烯二胺 作用下， 以 乙腈 为溶剂， 生成 Methyl 4-cyano-4-ethoxycarbonyloxy-4-(2-methoxyphenyl)-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.