trans-N,N'-dimethyl-N-allyl-1,2-cyclohexanediamine | 67198-25-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: trans-N,N'-dimethyl-N-allyl-1,2-cyclohexanediamine
• 英文别名: (1S,2S)-1-N,2-N-dimethyl-2-N-prop-2-enylcyclohexane-1,2-diamine
• CAS: 67198-25-8
• 化学式: C₁₁H₂₂N₂
• 分子量: 182.309
• InChiKey: MIMIUTJGEKNPLP-QWRGUYRKSA-N

物化性质

• 沸点：
  252.9±33.0 °C(Predicted)
• 密度：
  0.90±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  15.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  对羟基苯甲酰氯 、 trans-N,N'-dimethyl-N-allyl-1,2-cyclohexanediamine 在 三乙胺 作用下， 以 乙醚 为溶剂， 反应 17.0h， 生成 N-[(1S,2S)-2-(Allyl-methyl-amino)-cyclohexyl]-4-hydroxy-N-methyl-benzamide
  参考文献：
  名称：

  Factors affecting binding of trans-N-[2-(methylamino)cyclohexyl]benzamides at the primary morphine receptor

  摘要：

  In this paper, we describe the synthesis of a series of trans-N-[2-(methylamino)cyclohexyl]benzamides possessing morphine-like pharmacological properties. The affinity of the compounds for the agonist and antagonist states of the mu opioid receptor has been established by means of an in vitro binding assay. We have investigated the geometry and electronic structure of the molecules using molecular mechanics and an ab initio SCF-MO procedure with FSGO basis sets. Comparison to naloxone reveals properties of possible importance in receptor association. We have considered both the S,S and R,R isomers in the binding model. Statistical analyses imply that three factors play a significant role in binding: (1) membrane-water partitioning, (2) the capacity of the aromatic ring and amine N-substituent to act as electron acceptors, (3) the conformational energy required to attain the binding configuration.

  DOI：

  10.1021/jm00150a017
• 作为产物：
  描述：

  7-甲基-7-氮杂-双环[4.1.0]庚烷 、 N-甲基烯丙基胺 在 氯化铵 作用下， 以 水 为溶剂， 反应 16.0h， 以51%的产率得到trans-N,N'-dimethyl-N-allyl-1,2-cyclohexanediamine
  参考文献：
  名称：

  Factors affecting binding of trans-N-[2-(methylamino)cyclohexyl]benzamides at the primary morphine receptor

  摘要：

  In this paper, we describe the synthesis of a series of trans-N-[2-(methylamino)cyclohexyl]benzamides possessing morphine-like pharmacological properties. The affinity of the compounds for the agonist and antagonist states of the mu opioid receptor has been established by means of an in vitro binding assay. We have investigated the geometry and electronic structure of the molecules using molecular mechanics and an ab initio SCF-MO procedure with FSGO basis sets. Comparison to naloxone reveals properties of possible importance in receptor association. We have considered both the S,S and R,R isomers in the binding model. Statistical analyses imply that three factors play a significant role in binding: (1) membrane-water partitioning, (2) the capacity of the aromatic ring and amine N-substituent to act as electron acceptors, (3) the conformational energy required to attain the binding configuration.

  DOI：

  10.1021/jm00150a017

文献信息

• BE860727
  申请人：——

  公开号：——

  公开（公告）日：——
• BE860726
  申请人：——

  公开号：——

  公开（公告）日：——
• US4098904A
  申请人：——

  公开号：US4098904A

  公开（公告）日：1978-07-04
• US4145435A
  申请人：——

  公开号：US4145435A

  公开（公告）日：1979-03-20
• US4148914A
  申请人：——

  公开号：US4148914A

  公开（公告）日：1979-04-10