trans-2-methoxy-3,4,5,6,7,8,9,9a-octahydroquinoline | 103621-60-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吖庚因类
• 英文名称: trans-2-methoxy-3,4,5,6,7,8,9,9a-octahydroquinoline
• CAS: 103621-60-9
• 化学式: C₁₀H₁₇NO
• 分子量: 167.251
• InChiKey: ILQHZTUNVVCUDQ-BDAKNGLRSA-N

物化性质

• 沸点：
  238.5±9.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.38
• 重原子数：
  12.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  21.59
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  trans-2-methoxy-3,4,5,6,7,8,9,9a-octahydroquinoline 在 氯化铵 作用下， 以 乙醇 为溶剂， 生成 (4aR,8aS)-(Octahydro-quinolin-2-ylidene)amine
  参考文献：
  名称：

  Bicyclic amidine inhibitors of nitric oxide synthase: discovery of perhydro-iminopyrindine and perhydro-iminoquinoline as potent, orally active inhibitors of inducible nitric oxide synthase

  摘要：

  Syntheses and nitric oxide synthase inhibitory activity of cyclic amidines containing 5,6- 6,6- and 7,6-fused systems are described. X-ray structure determination facilitated the assignment of the stereochemistry of the most active compounds perhydro-2-iminoisoquinoline (8a) and perhydro-2-iminopyrindine (10a). Both 8a and 10a are very potent inhibitors of NOS, with excellent selectivity over eNOS and they are orally active in rats with long duration suitable for once or twice a day dosing. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.02.067
• 作为产物：
  描述：

  3,4,5,6,7,8-六氢-2(1H)-喹啉酮 在 甲酸 、 sodium formate 作用下， 以 二氯甲烷 为溶剂， 生成 trans-2-methoxy-3,4,5,6,7,8,9,9a-octahydroquinoline
  参考文献：
  名称：

  Bicyclic amidine inhibitors of nitric oxide synthase: discovery of perhydro-iminopyrindine and perhydro-iminoquinoline as potent, orally active inhibitors of inducible nitric oxide synthase

  摘要：

  Syntheses and nitric oxide synthase inhibitory activity of cyclic amidines containing 5,6- 6,6- and 7,6-fused systems are described. X-ray structure determination facilitated the assignment of the stereochemistry of the most active compounds perhydro-2-iminoisoquinoline (8a) and perhydro-2-iminopyrindine (10a). Both 8a and 10a are very potent inhibitors of NOS, with excellent selectivity over eNOS and they are orally active in rats with long duration suitable for once or twice a day dosing. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.02.067

文献信息

• Absence of stereoelectronic control in hydrolysis of cyclic amidines
  作者：Charles L. Perrin、Oswaldo. Nunez

  DOI：10.1021/ja00279a055

  日期：1986.9

  L'hydrolyse de trois amidines cycliques a 6 chainons donne essentiellement un aminoamide (produit de decyclisation) et seulement 3,9% de lactame (produit theorique). Par contre l'hydrolyse de trois amidines cycliques a 5 ou 7 chainons donne environ 50% de lactame

  L'hydrolyse de trois camides cycliques a 6 chainons donne essentiellement unaminoamide (produit de decyclisation) et seulement 3,9% de lactame (produit theorique)。Par contre l'hydrolyse de trois amidines cycliques a 5 ou 7 chainons donne environment 50% de内酰胺