(2Z,4E)-2-(3,4-dimethoxybenzylidene)-5-(trimethylsilyl)-pent-4-enenitrile | 1369278-48-7

• 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: (2Z,4E)-2-(3,4-dimethoxybenzylidene)-5-(trimethylsilyl)-pent-4-enenitrile
• 英文别名: (E,2Z)-2-[(3,4-dimethoxyphenyl)methylidene]-5-trimethylsilylpent-4-enenitrile
• CAS: 1369278-48-7
• 化学式: C₁₇H₂₃NO₂Si
• 分子量: 301.461
• InChiKey: MFQOPIIIBVESBR-RCTBWUFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.43
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  42.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2Z,4E)-2-(3,4-dimethoxybenzylidene)-5-(trimethylsilyl)-pent-4-enenitrile 在 4-二甲氨基吡啶 、 N-碘代丁二酰亚胺 、 六氟异丙醇 、 Parkin's catalyst 、 palladium diacetate 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 47.17h， 生成 tert-butyl ((2Z,4Z)-2-(3,4-dimethoxybenzylidene)-5-(3,4-dimethoxyphenyl)pent-4-enoyl)carbamate
  参考文献：
  名称：

  Transmissive Olefination Route to Putative “Morinol I” Lignans

  摘要：

  A series of morinol-type lignans were rapidly assembled using a Grignard-based transmissive olefination. In combination with palladium-catalyzed arylations, the strategy provides stereoselective access to (7Z,7'E), (7E,7'E), and (7E,7'Z) morinol diastereomers and the (7Z,8'E) and (7E,8'E) conjugated analogues. Critical for the E/Z stereoselectivity is a new, general method for converting alkenenitriles to alkenemethanols that circumvents the enal E/Z isomerization commonly encountered during conventional i-Bu2AlH reduction.

  DOI：

  10.1021/jo3001723
• 作为产物：
  描述：

  2-溴乙烯基三甲基硅烷 、 2-((3,4-dimethoxyphenyl)(hydroxy)methyl)acrylonitrile 在 magnesium 作用下， 以 四氢呋喃 、 1,2-二溴乙烷 、 1,2-bromoethane 为溶剂， 反应 4.0h， 以52%的产率得到(2Z,4E)-2-(3,4-dimethoxybenzylidene)-5-(trimethylsilyl)-pent-4-enenitrile
  参考文献：
  名称：

  Transmissive Olefination Route to Putative “Morinol I” Lignans

  摘要：

  A series of morinol-type lignans were rapidly assembled using a Grignard-based transmissive olefination. In combination with palladium-catalyzed arylations, the strategy provides stereoselective access to (7Z,7'E), (7E,7'E), and (7E,7'Z) morinol diastereomers and the (7Z,8'E) and (7E,8'E) conjugated analogues. Critical for the E/Z stereoselectivity is a new, general method for converting alkenenitriles to alkenemethanols that circumvents the enal E/Z isomerization commonly encountered during conventional i-Bu2AlH reduction.

  DOI：

  10.1021/jo3001723

文献信息

• Transmissive Olefination Route to Putative “Morinol I” Lignans
  作者：Lihua Yao、Bhaskar Pitta、P. C. Ravikumar、Matthew Purzycki、Fraser F. Fleming

  DOI：10.1021/jo3001723

  日期：2012.4.6

  A series of morinol-type lignans were rapidly assembled using a Grignard-based transmissive olefination. In combination with palladium-catalyzed arylations, the strategy provides stereoselective access to (7Z,7'E), (7E,7'E), and (7E,7'Z) morinol diastereomers and the (7Z,8'E) and (7E,8'E) conjugated analogues. Critical for the E/Z stereoselectivity is a new, general method for converting alkenenitriles to alkenemethanols that circumvents the enal E/Z isomerization commonly encountered during conventional i-Bu2AlH reduction.