9-aza-bicyclo[3.3.1]nonane-9-carboxylic acid methyl ester | 96424-17-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 9-aza-bicyclo[3.3.1]nonane-9-carboxylic acid methyl ester
• 英文别名: Methyl 9-azabicyclo[3.3.1]nonane-9-carboxylate
• CAS: 96424-17-8
• 化学式: C₁₀H₁₇NO₂
• 分子量: 183.25
• InChiKey: DCEIOSFQWYYLJG-UHFFFAOYSA-N

物化性质

• 沸点：
  260.8±9.0 °C(Predicted)
• 密度：
  1.081±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  9-aza-bicyclo[3.3.1]nonane-9-carboxylic acid methyl ester 在 碘代三甲硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 9-氮杂双环[3.3.1]壬烷
  参考文献：
  名称：

  Efficient oxidation of alcohols electrochemically mediated by azabicyclo-N-oxyls

  摘要：

  Preparation of azabicyclo-N-oxyls and the electrochemical oxidation of alcohols using them as mediators have been exploited. This oxidation was applicable to a transformation of sterically hindered secondary alcohols into the corresponding ketones in high yields. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.11.016
• 作为产物：
  描述：

  methyl (1R,3s,5S)-3-chloro-9-azabicyclo[3.3.1]nonane-9-carboxylate 在 Raney-Ni W-2 氢氧化钾 、 氢气 作用下， 以90%的产率得到9-aza-bicyclo[3.3.1]nonane-9-carboxylic acid methyl ester
  参考文献：
  名称：

  Efficient oxidation of alcohols electrochemically mediated by azabicyclo-N-oxyls

  摘要：

  Preparation of azabicyclo-N-oxyls and the electrochemical oxidation of alcohols using them as mediators have been exploited. This oxidation was applicable to a transformation of sterically hindered secondary alcohols into the corresponding ketones in high yields. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.11.016

文献信息

• Ring contraction of N-chlorolactams, a novel rearrangement
  作者：Alexandre Drouin、Jean Lessard

  DOI：10.1016/j.tetlet.2006.04.024

  日期：2006.6

  Upon photolysis in methylene chloride at −78 °C, different N-chlorolactams underwent a novel ring contraction to the corresponding carbamoyl chlorides, which were converted to the methyl carbamates. The rearrangement is 100% stereoselective, occurring with retention of configuration at the migrating carbon center. The yields of isolated carbamates ranged from 40% to 57%, the other product being the

  在-78°C的二氯甲烷中光解后，不同的N-氯内酰胺发生新的环收缩，生成相应的氨基甲酰氯，然后将其转化为氨基甲酸甲酯。重排是100％立体选择性的，发生构型保留在迁移的碳中心。分离的氨基甲酸酯的产率为40％至57％，另一种产物为母体内酰胺，产率为18％至38％。
• Barluenga, J.; Jimenez, C.; Najera, C., Journal of Heterocyclic Chemistry, 1984, vol. 21, p. 1733 - 1736
  作者：Barluenga, J.、Jimenez, C.、Najera, C.、Yus, M.

  DOI：——

  日期：——
• BARLUENGA, J.;JIMENEZ, C.;NAJERA, C.;YUS, M., J. HETEROCYCL. CHEM., 1984, 21, N 6, 1733-1736
  作者：BARLUENGA, J.、JIMENEZ, C.、NAJERA, C.、YUS, M.

  DOI：——

  日期：——
• Efficient oxidation of alcohols electrochemically mediated by azabicyclo-N-oxyls
  作者：Yosuke Demizu、Hirofumi Shiigi、Takahisa Oda、Yoshihiro Matsumura、Osamu Onomura

  DOI：10.1016/j.tetlet.2007.11.016

  日期：2008.1

  Preparation of azabicyclo-N-oxyls and the electrochemical oxidation of alcohols using them as mediators have been exploited. This oxidation was applicable to a transformation of sterically hindered secondary alcohols into the corresponding ketones in high yields. (C) 2007 Elsevier Ltd. All rights reserved.