(2RS,1'S,2'E) 2-(4-methoxybenzyloxy)hex-5-ynoic acid 4'-(tert-butyl(diphenyl)silyloxy)-1'-methylbut-2'-enyl ester | 851626-47-6

• 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)hex-5-ynoic acid 4'-(tert-butyl(diphenyl)silyloxy)-1'-methylbut-2'-enyl ester
• 英文别名: [(E,2S)-5-[tert-butyl(diphenyl)silyl]oxypent-3-en-2-yl] 2-[(4-methoxyphenyl)methoxy]hex-5-ynoate
• CAS: 851626-47-6
• 化学式: C₃₅H₄₂O₅Si
• 分子量: 570.801
• InChiKey: NJLWUXHJYSGMKR-OQVIWFLVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.06
• 重原子数：
  41
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  三甲基氯硅烷 、 (2RS,1'S,2'E) 2-(4-methoxybenzyloxy)hex-5-ynoic acid 4'-(tert-butyl(diphenyl)silyloxy)-1'-methylbut-2'-enyl ester 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.78h， 以98%的产率得到2-(4-Methoxy-benzyloxy)-6-trimethylsilanyl-hex-5-ynoic acid (E)-(S)-4-(tert-butyl-diphenyl-silanyloxy)-1-methyl-but-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
• 作为产物：
  描述：

  2-(4-Methoxy-benzyloxy)-5-oxo-pentanoic acid methyl ester 在 4-二甲氨基吡啶 、 barium dihydroxide 、 potassium carbonate 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 13.03h， 生成 (2RS,1'S,2'E) 2-(4-methoxybenzyloxy)hex-5-ynoic 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

• Highly enantioselective sequential Claisen–Ireland/metathesis: synthesis of cycloalkenes bearing two contiguous highly functionalized asymmetric centres
  作者：Antoine Français、Olivier Bedel、Willy Picoul、Abdelkrim Meddour、Jacques Courtieu、Arnaud Haudrechy

  DOI：10.1016/j.tetasy.2004.12.029

  日期：2005.3

  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.