8-甲基-8-氮杂双环[3.2.1]辛-6-烯 | 146309-01-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: 8-甲基-8-氮杂双环[3.2.1]辛-6-烯
• 英文名称: trop-6-ene
• 英文别名: Trop-6-en；8-Methyl-8-azabicyclo[3.2.1]oct-6-ene
• CAS: 146309-01-5
• 化学式: C₈H₁₃N
• 分子量: 123.198
• InChiKey: JHSWYRDVGAKWLT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  6-Oxa-7-aza-bicyclo[3.2.2]non-8-ene-7-carboxylic acid benzyl ester 在 lithium aluminium tetrahydride 、 氯化亚砜 、 lithium chloride 、 锌 作用下， 以 四氢呋喃 、 溶剂黄146 为溶剂， 反应 29.0h， 生成 8-甲基-8-氮杂双环[3.2.1]辛-6-烯
  参考文献：
  名称：

  Manipulation of substituents at nitrogen in tropanes, homotropanes, and dehydro- derivatives

  摘要：

  Trop-6-ene (8-methyl-8-azabicyclo[3.2.1]oct-6-ene) and substituted N-benzylnortrop-6-enes are synthesised. N-Debenzylation of tropanes fails using a wide variety of non-hydrogenolytic conditions despite effective application in model piperidine derivatives; debenzylation of homotropanes is more successful, giving norhomotropane and norhomotrop-7-ene. Bridged N-benzyl compounds react more slowly than N-methyl analogues with chloroformates; the resulting quaternary intermediates are more prone than the N-methyl analogues to suffer competitive reversion to the starting amine, especially in the tropanes, consistent with slower S(N)2 attack at the benzylic carbon during decomposition; the use of an N-p-methoxybenzyl group does allow partial debenzylation to nortrop-6-ene, suggesting greater SNI character in the decomposition step in this case. 'Equatorial' attack is preferred in methylation of N-benzyl-nortrop-6-ene and -homotrop-7-ene with CH3I; subsequent reductive debenzylation of the quaternary salt achieves overall replacement of N-benzyl by N-methyl in both cases. VT NMR studies show the presence of a single 'equatorial' invertomer (Cl syn- to the 2C-bridge) in N-chloro-norhomotropanes and -7-enes and, by analogy, in the N-alkyl compounds. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00643-7

文献信息

• Willstaetter, Chemische Berichte, 1901, vol. 34, p. 134
  作者：Willstaetter

  DOI：——

  日期：——
• BILE ACID DERIVATIVES AS FXR/TGR5 AGONISTS AND METHODS OF USE THEREOF
  申请人：ENANTA PHARMACEUTICALS, INC.

  公开号：US20160289262A1

  公开（公告）日：2016-10-06

  The present invention provides compounds represented by Formula I, or pharmaceutically acceptable salts, stereoisomers, solvates, hydrates or combination thereof, The invention also provides pharmaceutical compositions comprising these compounds and methods of using this compounds for treating FXR-mediated or TGR5-mediated diseases or conditions.
• Manipulation of substituents at nitrogen in tropanes, homotropanes, and dehydro- derivatives
  作者：Nicola M. Howarth、John R. Malpass、Craig R. Smith

  DOI：10.1016/s0040-4020(98)00643-7

  日期：1998.9

  Trop-6-ene (8-methyl-8-azabicyclo[3.2.1]oct-6-ene) and substituted N-benzylnortrop-6-enes are synthesised. N-Debenzylation of tropanes fails using a wide variety of non-hydrogenolytic conditions despite effective application in model piperidine derivatives; debenzylation of homotropanes is more successful, giving norhomotropane and norhomotrop-7-ene. Bridged N-benzyl compounds react more slowly than N-methyl analogues with chloroformates; the resulting quaternary intermediates are more prone than the N-methyl analogues to suffer competitive reversion to the starting amine, especially in the tropanes, consistent with slower S(N)2 attack at the benzylic carbon during decomposition; the use of an N-p-methoxybenzyl group does allow partial debenzylation to nortrop-6-ene, suggesting greater SNI character in the decomposition step in this case. 'Equatorial' attack is preferred in methylation of N-benzyl-nortrop-6-ene and -homotrop-7-ene with CH3I; subsequent reductive debenzylation of the quaternary salt achieves overall replacement of N-benzyl by N-methyl in both cases. VT NMR studies show the presence of a single 'equatorial' invertomer (Cl syn- to the 2C-bridge) in N-chloro-norhomotropanes and -7-enes and, by analogy, in the N-alkyl compounds. (C) 1998 Elsevier Science Ltd. All rights reserved.