tert-butyl (2Z,4E)-2-(3,4-dimethoxybenzylidene)-5-(3,4-dimethoxyphenyl)pent-4-enoylcarbamate | 1369278-47-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: tert-butyl (2Z,4E)-2-(3,4-dimethoxybenzylidene)-5-(3,4-dimethoxyphenyl)pent-4-enoylcarbamate
• 英文别名: tert-butyl N-[(E,2Z)-5-(3,4-dimethoxyphenyl)-2-[(3,4-dimethoxyphenyl)methylidene]pent-4-enoyl]carbamate
• CAS: 1369278-47-6
• 化学式: C₂₇H₃₃NO₇
• 分子量: 483.562
• InChiKey: DEPDCAJLJSVZEC-FPEKVXROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  92.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tert-butyl (2Z,4E)-2-(3,4-dimethoxybenzylidene)-5-(3,4-dimethoxyphenyl)pent-4-enoylcarbamate 在 三乙基硼氢化锂 、 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.5h， 以72%的产率得到morinol I
  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：

  (Z)-2-(3,4-dimethoxybenzylidene)pent-4-enenitrile 在 4-二甲氨基吡啶 、 Parkin's catalyst 、 palladium diacetate 、 silver carbonate 作用下， 以 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 35.0h， 生成 tert-butyl (2Z,4E)-2-(3,4-dimethoxybenzylidene)-5-(3,4-dimethoxyphenyl)pent-4-enoylcarbamate
  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.