O-Ethoxycarbonylmandelnitril | 98188-39-7

• 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: O-Ethoxycarbonylmandelnitril
• 英文别名: [Cyano(phenyl)methyl] propanoate；[cyano(phenyl)methyl] propanoate
• CAS: 98188-39-7
• 化学式: C₁₁H₁₁NO₂
• 分子量: 189.214
• InChiKey: TYCQSAVCOHNLCV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  methyl 2-(((tert-butoxycarbonyl)oxy)methyl)acrylate 、 O-Ethoxycarbonylmandelnitril 在 三乙烯二胺 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以89%的产率得到methyl 4-cyano-2-methylene-4-phenyl-4-(propionyloxy)butanoate
  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：

  三甲基氰硅烷 、 苯甲醛 、 丙酸酐 在 三氯化铁 作用下， 以 硝基甲烷 为溶剂， 反应 3.5h， 以95%的产率得到O-Ethoxycarbonylmandelnitril
  参考文献：
  名称：

  An efficient and facile one-pot synthesis of cyanohydrin esters from carbonyl compounds catalyzed by iron(III) chloride

  摘要：

  A variety of cyanohydrin esters were readily prepared from carbonyl compounds with trimethylsilyl cyanide and acid anhydride under the influence of a catalytic amount of iron(III) chloride in a convenient one-pot procedure. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.09.003

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.
• An efficient and facile one-pot synthesis of cyanohydrin esters from carbonyl compounds catalyzed by iron(III) chloride
  作者：Katsuyuki Iwanami、Masaru Aoyagi、Takeshi Oriyama

  DOI：10.1016/j.tetlet.2005.09.003

  日期：2005.10

  A variety of cyanohydrin esters were readily prepared from carbonyl compounds with trimethylsilyl cyanide and acid anhydride under the influence of a catalytic amount of iron(III) chloride in a convenient one-pot procedure. (c) 2005 Elsevier Ltd. All rights reserved.