2-Methyl-4-(2',2',6'-trimethylcyclohex-1'-enyl)-2-trimethylsilyloxybutyronitrile | 144653-99-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2-Methyl-4-(2',2',6'-trimethylcyclohex-1'-enyl)-2-trimethylsilyloxybutyronitrile
• 英文别名: 2-Methyl-4-(2,6,6-trimethylcyclohexen-1-yl)-2-trimethylsilyloxybutanenitrile
• CAS: 144653-99-6
• 化学式: C₁₇H₃₁NOSi
• 分子量: 293.525
• InChiKey: HHXOXVUPRURYIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.43
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-Methyl-4-(2',2',6'-trimethylcyclohex-1'-enyl)-2-trimethylsilyloxybutyronitrile 在 硫酸 、 二异丁基氢化铝 、 氯化铵 作用下， 反应 13.5h， 生成 2-<4',5'-Dihydroxy-5'-methyl-7'-(2'',2'',6''-trimethylcyclohex-1''-enyl)heptanoyl>-1-methoxymethylimidazole
  参考文献：
  名称：

  Synthesis of γ-lactones from intermediate 2-(γ-hydroxyacyl)-imidazoles by N-methylation and base-catalyzed C  C bond cleavage. Application to the synthesis of (±)- cavernosine

  摘要：

  Reaction of the allyl anions of 0-trialkylsilyl-N-alkyl-2-(1'-hydroxyprop-2'-enyl)imidazoles with aldehydes and ketones gives products of alpha- and gamma-attack. Greater steric hindrance in the anion (triisopropylsilyl VS t-butyldimethylsilyl) and in the aldehyde or ketone favours the gamma-products. Sequential desilylation, N-methylation and treatment with base resulted in cleavage of these products to gamma-lactones. The method was applied to the synthesis of (+/-)-cavernosine.

  DOI：

  10.1016/s0040-4020(01)80461-0
• 作为产物：
  描述：

  三甲基氰硅烷 、 BETA-二氢紫罗兰酮 在 zinc(II) iodide 作用下， 以 二氯甲烷 为溶剂， 以92%的产率得到2-Methyl-4-(2',2',6'-trimethylcyclohex-1'-enyl)-2-trimethylsilyloxybutyronitrile
  参考文献：
  名称：

  Synthesis of γ-lactones from intermediate 2-(γ-hydroxyacyl)-imidazoles by N-methylation and base-catalyzed C  C bond cleavage. Application to the synthesis of (±)- cavernosine

  摘要：

  Reaction of the allyl anions of 0-trialkylsilyl-N-alkyl-2-(1'-hydroxyprop-2'-enyl)imidazoles with aldehydes and ketones gives products of alpha- and gamma-attack. Greater steric hindrance in the anion (triisopropylsilyl VS t-butyldimethylsilyl) and in the aldehyde or ketone favours the gamma-products. Sequential desilylation, N-methylation and treatment with base resulted in cleavage of these products to gamma-lactones. The method was applied to the synthesis of (+/-)-cavernosine.

  DOI：

  10.1016/s0040-4020(01)80461-0

文献信息

• Synthesis of γ-lactones from intermediate 2-(γ-hydroxyacyl)-imidazoles by N-methylation and base-catalyzed C  C bond cleavage. Application to the synthesis of (±)- cavernosine
  作者：D.Huw Davies、Nicholas A. Haire、Jonathan Hall、Edward H. Smith

  DOI：10.1016/s0040-4020(01)80461-0

  日期：1992.1

  Reaction of the allyl anions of 0-trialkylsilyl-N-alkyl-2-(1'-hydroxyprop-2'-enyl)imidazoles with aldehydes and ketones gives products of alpha- and gamma-attack. Greater steric hindrance in the anion (triisopropylsilyl VS t-butyldimethylsilyl) and in the aldehyde or ketone favours the gamma-products. Sequential desilylation, N-methylation and treatment with base resulted in cleavage of these products to gamma-lactones. The method was applied to the synthesis of (+/-)-cavernosine.