α-iso-propylbenzeneacetic acid phenyl ester | 351874-82-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: α-iso-propylbenzeneacetic acid phenyl ester
• 英文别名: Phenyl 3-methyl-2-phenylbutanoate；phenyl 3-methyl-2-phenylbutanoate
• CAS: 351874-82-3
• 化学式: C₁₇H₁₈O₂
• 分子量: 254.329
• InChiKey: ZHMODXRNFKSTMW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl 2-(10,16-dimethyl-13-oxo-12,14-dioxa-13λ5-phosphapentacyclo[13.8.0.02,11.03,8.018,23]tricosa-1(15),2(11),3,5,7,9,16,18,20,22-decaen-13-yl)acetate 、 α-iso-propylbenzeneacetic acid phenyl ester 在 zinc(II) chloride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 生成 (aS)-(+)-5-methyl-4-phenyl-2,3-hexadienoic acid methyl ester 、 (aS)-(+)-5-methyl-4-phenyl-2,3-hexadienoic acid methyl ester
  参考文献：
  名称：

  Enantioselective synthesis of allenecarboxylates from phenyl acetates through CC bond forming reactions

  摘要：

  A variety of optically active 4,4-disubstituted allenecarboxylic acid methyl esters were prepared from simple alpha,alpha -disubstituted phenyl acetate through base treatment of the esters to generate ketenes, followed by successive Horner-Wadsworth-Emmons reaction. The transformation was further developed as a one-pot procedure with satisfactory yields and high enantioselectivity. (C) 2001 EIsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00114-8
• 作为产物：
  描述：

  2-碘代丙烷 、 苯乙酸苯酯 在 六甲基磷酰三胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 以22%的产率得到α-iso-propylbenzeneacetic acid phenyl ester
  参考文献：
  名称：

  Enantioselective synthesis of allenecarboxylates from phenyl acetates through CC bond forming reactions

  摘要：

  A variety of optically active 4,4-disubstituted allenecarboxylic acid methyl esters were prepared from simple alpha,alpha -disubstituted phenyl acetate through base treatment of the esters to generate ketenes, followed by successive Horner-Wadsworth-Emmons reaction. The transformation was further developed as a one-pot procedure with satisfactory yields and high enantioselectivity. (C) 2001 EIsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00114-8

文献信息

• Enantioselective synthesis of allenecarboxylates from phenyl acetates through CC bond forming reactions
  作者：Jiro Yamazaki、Toshiyuki Watanabe、Kiyoshi Tanaka

  DOI：10.1016/s0957-4166(01)00114-8

  日期：2001.3

  A variety of optically active 4,4-disubstituted allenecarboxylic acid methyl esters were prepared from simple alpha,alpha -disubstituted phenyl acetate through base treatment of the esters to generate ketenes, followed by successive Horner-Wadsworth-Emmons reaction. The transformation was further developed as a one-pot procedure with satisfactory yields and high enantioselectivity. (C) 2001 EIsevier Science Ltd. All rights reserved.