N-methyl-9-azabicyclo[4.2.1]non-7-ene | 139682-26-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环庚烷
• 英文名称: N-methyl-9-azabicyclo[4.2.1]non-7-ene
• 英文别名: 9-Methyl-9-azabicyclo[4.2.1]non-7-ene
• CAS: 139682-26-1
• 化学式: C₉H₁₅N
• 分子量: 137.225
• InChiKey: HWEQBRZSUJKZIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-methyl-9-azabicyclo[4.2.1]non-7-ene 在 1-氯乙基氯甲酸酯 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 N-(Benzyloxycarbonyl)-9-azabicyclo[4.2.1]non-7-ene
  参考文献：
  名称：

  Synthesis and nicotinic acetylcholine-binding properties of epibatidine homologues: homoepibatidine and dihomoepibatidine

  摘要：

  高催眠素2和二高催眠素3已分别从8-氮杂双环[3.2.1]辛-6-烯8和9-氮杂双环[4.2.1]辛-7-烯9合成，它们是还原性Heck耦合反应的关键前体。描述了从环庚-1,3-二烯和环辛-1,3-二烯开始的替代路线；莨菪烷和同莨菪烷环氧化合物的脱氧作用为8和9提供了一条便捷的合成路线。2的对映异构体在烟碱受体上的效能与相应的催眠素对映异构体相似；3的亲和性较低。

  DOI：

  10.1039/b010178h

文献信息

• Synthesis of epibatidine homologues: Homoepibatidine and bis-homoepibatidine
  作者：John R Malpass、David A Hemmings、Anna L Wallis

  DOI：10.1016/0040-4039(96)00687-9

  日期：1996.5

  based, respectively, on the tropane (8-azabicyclo[3.2.1]octane) and homotropane (9-azabicyclo[4.2.1]nonane) ring systems. Epoxy- tropanes and -homotropanes (which are readily available from simple cyclic dienes) are convenient precursors for the azabicyclic alkenes needed for the key reductive coupling with pyridine derivatives.

  描述了合成方法，它们导致高乙哌啶和双高哌啶，它们分别基于环烷（8-氮杂双环[3.2.1]辛烷）和高乙烷（9-氮杂双环[4.2.1]壬烷）环系。环氧-托环烷和-同高环烷（可从简单的环状二烯容易获得）是与吡啶衍生物进行关键还原偶联所需的氮杂双环烯烃的便利前体。
• 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.
• Synthesis and nicotinic acetylcholine-binding properties of epibatidine homologues: homoepibatidine and dihomoepibatidine
  作者：John R. Malpass、David A. Hemmings、Anna L. Wallis、Stephen R. Fletcher、Shailendra Patel

  DOI：10.1039/b010178h

  日期：——

  Homoepibatidine 2 and dihomoepibatidine 3 have been synthesised from the 8-azabicyclo[3.2.1]oct-6-ene 8 and the 9-azabicyclo[4.2.1]oct-7-ene 9, respectively, the key precursors for reductive Heck coupling reactions. Alternative routes starting from cyclohepta- and cycloocta-1,3-diene are described; deoxygenation of tropane and homotropane epoxides provides a convenient route to 8 and 9. The enantiomers of 2 show similar potency at nicotinic receptors to the corresponding epibatidine enantiomers; the affinity of 3 is lower.

  高催眠素2和二高催眠素3已分别从8-氮杂双环[3.2.1]辛-6-烯8和9-氮杂双环[4.2.1]辛-7-烯9合成，它们是还原性Heck耦合反应的关键前体。描述了从环庚-1,3-二烯和环辛-1,3-二烯开始的替代路线；莨菪烷和同莨菪烷环氧化合物的脱氧作用为8和9提供了一条便捷的合成路线。2的对映异构体在烟碱受体上的效能与相应的催眠素对映异构体相似；3的亲和性较低。