(Z)-5-methyl-1-phenylhexa-2,4-dien-3-yl N,N-diisopropylcarbamate | 905444-35-1

• 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: (Z)-5-methyl-1-phenylhexa-2,4-dien-3-yl N,N-diisopropylcarbamate
• 英文别名: [(2Z)-5-methyl-1-phenylhexa-2,4-dien-3-yl] N,N-di(propan-2-yl)carbamate
• CAS: 905444-35-1
• 化学式: C₂₀H₂₉NO₂
• 分子量: 315.456
• InChiKey: JYRVVMHHWXAYDX-UYRXBGFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-5-methyl-1-phenylhexa-2,4-dien-3-yl N,N-diisopropylcarbamate 、 对溴苯甲醛 在 正丁基锂 、 四甲基乙二胺 、 tris(diethylamide)titanium chloride 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 4.0h， 生成 (1E,3Z)-6-(4-bromophenyl)-6-hydroxy-5,5-dimethyl-1-phenylhexa-1,3-dien-3-yl N,N-diisopropylcarbamate 、 (6RS,7SR,4Z)-7-(4-bromophenyl)-7-hydroxy-2-methyl-6-phenylhepta-2,4-dien-4-yl N,N-diisopropylcarbamate
  参考文献：
  名称：

  Asymmetric γ-Deprotonation and Homoaldol Reaction of 1,3-Dien-2-yl Carbamates:  Stereo- and Regiochemistry

  摘要：

  [GRAPHICS]Lithium compounds 7 are configurationally stable intermediates obtained by deprotonation of 1,3-dien-2-yl carbamates 6 with n-butyllithium/(-)-sparteine with a high degree of enantiotopic differentiation at the gamma-position. They react with electrophiles regioselectively giving highly enantioenriched products. Starting with different isomers or changing the double-bond geometries in 6 leads to either of the enantiomers.

  DOI：

  10.1021/ol061005p
• 作为产物：
  描述：

  1-溴-2-甲基-1-丙烯 、 (Z)-3-苯基-1-丙烯基N,n-二异丙基氨基甲酸酯 在 四(三苯基膦)钯 正丁基锂 、 四甲基乙二胺 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 13.92h， 以74%的产率得到(Z)-5-methyl-1-phenylhexa-2,4-dien-3-yl N,N-diisopropylcarbamate
  参考文献：
  名称：

  Asymmetric γ-Deprotonation and Homoaldol Reaction of 1,3-Dien-2-yl Carbamates:  Stereo- and Regiochemistry

  摘要：

  [GRAPHICS]Lithium compounds 7 are configurationally stable intermediates obtained by deprotonation of 1,3-dien-2-yl carbamates 6 with n-butyllithium/(-)-sparteine with a high degree of enantiotopic differentiation at the gamma-position. They react with electrophiles regioselectively giving highly enantioenriched products. Starting with different isomers or changing the double-bond geometries in 6 leads to either of the enantiomers.

  DOI：

  10.1021/ol061005p

文献信息

• Asymmetric γ-Deprotonation and Homoaldol Reaction of 1,3-Dien-2-yl Carbamates:  Stereo- and Regiochemistry
  作者：Roland Bou Chedid、Roland Fröhlich、Dieter Hoppe

  DOI：10.1021/ol061005p

  日期：2006.7.1

  [GRAPHICS]Lithium compounds 7 are configurationally stable intermediates obtained by deprotonation of 1,3-dien-2-yl carbamates 6 with n-butyllithium/(-)-sparteine with a high degree of enantiotopic differentiation at the gamma-position. They react with electrophiles regioselectively giving highly enantioenriched products. Starting with different isomers or changing the double-bond geometries in 6 leads to either of the enantiomers.