(1-Cyano-3-methoxycarbonyl-1-phenylbut-3-enyl) benzoate | 1346232-11-8

• 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: (1-Cyano-3-methoxycarbonyl-1-phenylbut-3-enyl) benzoate
• CAS: 1346232-11-8
• 化学式: C₂₀H₁₇NO₄
• 分子量: 335.359
• InChiKey: XJFGWLCPXBMSQY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  76.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1-Cyano-3-methoxycarbonyl-1-phenylbut-3-enyl) benzoate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 43.0h， 以67%的产率得到methyl 3-benzoyl-2-(cyanomethyl)-4-oxo-4-phenylbutanoate
  参考文献：
  名称：

  Lewis Base-Promoted Rearrangement of Allylic Cyanohydrins: Construction of Functionalized Nitriles Bearing 1,3-Diketone Moieties

  摘要：

  A novel Lewis base-promoted rearrangement of allylic cyanohydrins has been developed, in which the cyano group was rearranged, directly coupled with the generation of new functional groups. This protocol provides a unique and facile way to prepare highly functionalized nitriles bearing 1,3-diketone moieties under mild reaction conditions. Furthermore, the synthetic transformations of the functionalized products have also been demonstrated.

  DOI：

  10.1021/jo501909w
• 作为产物：
  描述：

  methyl 2-(((tert-butoxycarbonyl)oxy)methyl)acrylate 、 2-(苯甲酰氧基)-2-苯基乙腈 在 三乙烯二胺 、 二碳酸二叔丁酯 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以83%的产率得到(1-Cyano-3-methoxycarbonyl-1-phenylbut-3-enyl) benzoate
  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

文献信息

• 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.