(-)-(1S)-N,4-dimethyl-N-(4-methyl-3-cyclohexenyl)-3-pentenamide | 141484-04-0

• 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: (-)-(1S)-N,4-dimethyl-N-(4-methyl-3-cyclohexenyl)-3-pentenamide
• 英文别名: (S)-N,4-dimethyl-N-(4-methylcyclohex-3-en-1-yl)pent-3-enamide；N,4-dimethyl-N-[(1S)-4-methylcyclohex-3-en-1-yl]pent-3-enamide
• CAS: 141484-04-0
• 化学式: C₁₄H₂₃NO
• 分子量: 221.343
• InChiKey: UIMNCVAPQNPZOE-CYBMUJFWSA-N

物化性质

• 沸点：
  329.1±32.0 °C(Predicted)
• 密度：
  0.95±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  20.31
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (-)-(1S)-N,4-dimethyl-N-(4-methyl-3-cyclohexenyl)-3-pentenamide 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 18.0h， 生成 (-)-(1S)-N,4-二甲基-N-(4-甲基-3-戊烯基)-3-环己烯胺
  参考文献：
  名称：

  Silent catalytic promiscuity in the high-fidelity terpene cyclase δ-cadinene synthase

  摘要：

  碳正离子的Aza类似物抑制δ-卡丁烯合酶：1,6-环化。

  DOI：

  10.1039/c8ob02821d
• 作为产物：
  描述：

  (R)-2-<(S)-4-methyl-3-cyclohexene-1-carboxy>-3,3-dimethyl-γ-butyrolactone 在 lithium aluminium tetrahydride 、 叠氮磷酸二苯酯 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 、 N,N-二异丙基乙胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 49.33h， 生成 (-)-(1S)-N,4-dimethyl-N-(4-methyl-3-cyclohexenyl)-3-pentenamide
  参考文献：
  名称：

  Silent catalytic promiscuity in the high-fidelity terpene cyclase δ-cadinene synthase

  摘要：

  碳正离子的Aza类似物抑制δ-卡丁烯合酶：1,6-环化。

  DOI：

  10.1039/c8ob02821d

文献信息

• Trichodiene synthase. Synergistic inhibition by inorganic pyrophosphate and aza analogs of the bisabolyl cation.
  作者：David E. Cane、Guohan Yang、Robert M. Coates、Hyung Jung Pyun、Thomas M. Hohn

  DOI：10.1021/jo00038a040

  日期：1992.6

  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.