(1R)-1-叠氮基-4-甲基-3-环己烯 | 141484-08-4

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 中文名称: (1R)-1-叠氮基-4-甲基-3-环己烯
• 英文名称: (1R)-1-azido-4-methyl-3-cyclohexene
• 英文别名: (4R)-4-azido-1-methylcyclohexene
• CAS: 141484-08-4
• 化学式: C₇H₁₁N₃
• 分子量: 137.184
• InChiKey: JORNWVQJHOPUSX-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  14.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R)-1-叠氮基-4-甲基-3-环己烯 在 吡啶 、 lithium aluminium tetrahydride 、 N,N'-羰基二咪唑 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 29.5h， 生成 (+)-(1R)-N,4-dimethyl-N-(4-methyl-3-pentenyl)-3-cyclohexenamine
  参考文献：
  名称：

  Trichodiene synthase. Synergistic inhibition by inorganic pyrophosphate and aza analogs of the bisabolyl cation.

  摘要：

  A series of aza analogs of the bisabolyl and alpha-terpinyl cations were tested as inhibitors of the sesquiterpene cyclase, trichodiene synthase. Both (R)- and (S)-16 and (R)- and (S)-13 as well as trimethylamine were only weak inhibitors when incubated alone. In the presence of inorganic pyrophosphate, itself a known competitive inhibitor of trichodiene synthase, all five amines showed strong cooperative competitive inhibition with an enhancement factor estimated to be 10-40. The apparent induced inhibition constant alpha-K(j) decreased in going from trimethylamine to the monoterpene analogs 13 and was strongest for the sesquiterpene analogs 16, indicating that both electrostatic and hydrophobic interactions are important in the binding of each intermediate analog. The cyclase showed little discrimination, however, between the individual enantiomers of each inhibitor.

  DOI：

  10.1021/jo00038a040
• 作为产物：
  描述：

  吡啶，1,2-二氢-4,5,6-三甲基-2-亚甲基-(9CI) 在 吡啶 、 lithium aluminium tetrahydride 、 sodium azide 、 sodium acetate 、 溶剂黄146 、 间氯过氧苯甲酸 、 sodium iodide 、 锌 作用下， 以 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 73.5h， 生成 (1R)-1-叠氮基-4-甲基-3-环己烯
  参考文献：
  名称：

  Trichodiene synthase. Synergistic inhibition by inorganic pyrophosphate and aza analogs of the bisabolyl cation.

  摘要：

  A series of aza analogs of the bisabolyl and alpha-terpinyl cations were tested as inhibitors of the sesquiterpene cyclase, trichodiene synthase. Both (R)- and (S)-16 and (R)- and (S)-13 as well as trimethylamine were only weak inhibitors when incubated alone. In the presence of inorganic pyrophosphate, itself a known competitive inhibitor of trichodiene synthase, all five amines showed strong cooperative competitive inhibition with an enhancement factor estimated to be 10-40. The apparent induced inhibition constant alpha-K(j) decreased in going from trimethylamine to the monoterpene analogs 13 and was strongest for the sesquiterpene analogs 16, indicating that both electrostatic and hydrophobic interactions are important in the binding of each intermediate analog. The cyclase showed little discrimination, however, between the individual enantiomers of each inhibitor.

  DOI：

  10.1021/jo00038a040