(1R,6R)-2-(1-Ethoxy-vinyl)-9-aza-bicyclo[4.2.1]non-2-ene-9-carboxylic acid ethyl ester | 281650-64-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (1R,6R)-2-(1-Ethoxy-vinyl)-9-aza-bicyclo[4.2.1]non-2-ene-9-carboxylic acid ethyl ester
• CAS: 281650-64-4
• 化学式: C₁₅H₂₃NO₃
• 分子量: 265.353
• InChiKey: NCQLWDKQSWYFMO-TZMCWYRMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.25
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  38.77
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1R,6R)-2-(1-Ethoxy-vinyl)-9-aza-bicyclo[4.2.1]non-2-ene-9-carboxylic acid ethyl ester 在 氢溴酸 、 silica gel 、 溶剂黄146 作用下， 生成 (+)-(1R)-2-acetyl-9-azabicyclo[4.2.1]non-2-ene-9-carboxylic acid ethyl ester
  参考文献：
  名称：

  A new and efficient synthetic route to enantiopure (+)-anatoxin-a from (−)-cocaine hydrochloride

  摘要：

  The potent nAChR agonist (+)-anatoxin-a was efficiently synthesized in enantiomerically pure form starting from a readily available confiscated grade (-)-cocaine hydrochloride. The eight-step synthesis providing novel extensions to existing methodology proceeded with 26% overall yield and with stereochemical integrity of the relevant original stereogenic centers. Key steps were an effective ring expansion of the (+)-2-tropinone 2 to the 9-azabicyclo[4.2.1]nonanone 5 with TMSCHN2/Al(CH3)(3) and the introduction of the required methyl ketone side chain in masked form by reacting the corresponding enol triflate 6 with ethyl vinyl ether/Pd(OAc2) under Heck reaction conditions. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00059-8
• 作为产物：
  描述：

  (-)-(1R)-2-oxo-9-azabicyclo[4.2.1]nonane-9-carboxylic acid ethyl ester 在 palladium diacetate 、 双(三甲基硅烷基)氨基钾 、 三乙胺 作用下， 以 四氢呋喃 、 二甲基亚砜 、 甲苯 为溶剂， 反应 7.0h， 生成 (1R,6R)-2-(1-Ethoxy-vinyl)-9-aza-bicyclo[4.2.1]non-2-ene-9-carboxylic acid ethyl ester
  参考文献：
  名称：

  A new and efficient synthetic route to enantiopure (+)-anatoxin-a from (−)-cocaine hydrochloride

  摘要：

  The potent nAChR agonist (+)-anatoxin-a was efficiently synthesized in enantiomerically pure form starting from a readily available confiscated grade (-)-cocaine hydrochloride. The eight-step synthesis providing novel extensions to existing methodology proceeded with 26% overall yield and with stereochemical integrity of the relevant original stereogenic centers. Key steps were an effective ring expansion of the (+)-2-tropinone 2 to the 9-azabicyclo[4.2.1]nonanone 5 with TMSCHN2/Al(CH3)(3) and the introduction of the required methyl ketone side chain in masked form by reacting the corresponding enol triflate 6 with ethyl vinyl ether/Pd(OAc2) under Heck reaction conditions. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00059-8