(2RS,1'S,2'E) 2-(4-methoxybenzyloxy)pent-4-enoic acid 4'-(tert-butyl(diphenyl)silyloxy)-1'-methylbut-2'-enyl ester | 851626-39-6

• 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: (2RS,1'S,2'E) 2-(4-methoxybenzyloxy)pent-4-enoic acid 4'-(tert-butyl(diphenyl)silyloxy)-1'-methylbut-2'-enyl ester
• CAS: 851626-39-6
• 化学式: C₃₄H₄₂O₅Si
• 分子量: 558.79
• InChiKey: WTEVHGCPNQNTJP-ZNEVEVKYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.22
• 重原子数：
  40.0
• 可旋转键数：
  14.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2RS,1'S,2'E) 2-(4-methoxybenzyloxy)pent-4-enoic acid 4'-(tert-butyl(diphenyl)silyloxy)-1'-methylbut-2'-enyl ester 在 双(三甲基硅烷基)氨基钾 、 三甲基氯硅烷 作用下， 以 甲苯 为溶剂， 反应 1.0h， 生成 (2S,3S)-2-Allyl-3-(tert-butyl-diphenyl-silanyloxymethyl)-2-(4-methoxy-benzyloxy)-pent-4-enoic acid
  参考文献：
  名称：

  Highly enantioselective sequential Claisen–Ireland/metathesis: synthesis of cycloalkenes bearing two contiguous highly functionalized asymmetric centres

  摘要：

  A sequence of two reactions, consisting of a highly stereoselective silylated ketene acetal Claisen-Ireland rearrangement followed by a ring closing metathesis, gave a stereocontrolled access to various carbocycles. (C) 2005 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2004.12.029
• 作为产物：
  描述：

  2-羟基-4-戊烯酸 在 4-二甲氨基吡啶 、 sodium hydride 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2RS,1'S,2'E) 2-(4-methoxybenzyloxy)pent-4-enoic acid 4'-(tert-butyl(diphenyl)silyloxy)-1'-methylbut-2'-enyl ester
  参考文献：
  名称：

  Highly enantioselective sequential Claisen–Ireland/metathesis: synthesis of cycloalkenes bearing two contiguous highly functionalized asymmetric centres

  摘要：

  A sequence of two reactions, consisting of a highly stereoselective silylated ketene acetal Claisen-Ireland rearrangement followed by a ring closing metathesis, gave a stereocontrolled access to various carbocycles. (C) 2005 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2004.12.029

文献信息

• Directed Diastereoselectivity in the Asymmetric Claisen/Metathesis Reaction Sequence
  作者：Nicolas P. Probst、Arnaud Haudrechy、Karen Plé

  DOI：10.1021/jo800496h

  日期：2008.6.1

  The Claisen/metathesis sequence is a versatile synthetic tool for the synthesis of quaternary hydroxy and amino acid carbocycles. By correctly choosing both the configuration of the allylic alcohol and the double bond geometry, specific access to any one of four possible stereoisomers is possible in good yield and excellent diastereoselectivity. The enantiomerically pure allylic alcohols are easily obtained by addition of terminal alkynes to aldehydes. Controlled reduction of the triple bond then gives the desired double bond geometry.