1-azabicyclo[4.1.0]heptane | 286-30-6

• 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: 1-azabicyclo[4.1.0]heptane
• 英文别名: 1-aza-bicyclo[4.1.0]heptane；azabicyclo [4.1.0]heptane；DL-1-Azabicyclo<4.1.0>heptan；Azabicyclo[4.1.0]heptane
• CAS: 286-30-6
• 化学式: C₆H₁₁N
• 分子量: 97.16
• InChiKey: BLOINAPUWZYQMD-UHFFFAOYSA-N

物化性质

• 沸点：
  127.8±8.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-甲基糠基胺 、 1-azabicyclo[4.1.0]heptane 在 sodium hydroxide 、 potassium carbonate 作用下， 以 水 为溶剂， 生成 trans-2-[N-methyl-N-(furan-2-ylmethyl)amino]cyclohexylamine
  参考文献：
  名称：

  Analgesic N-[2-(furyl-methylamino and 2-thienylmethylamino)cycloaliphatic]b

  摘要：

  顺式和反式-N-(2-氨基环脂环烷基)苯甲酰胺化合物的化学式为##STR1## 例如，N-甲基-N-[2-[(2-呋喃甲基)甲基氨基]-环己基]-3,4-二氯苯甲酰胺，及其药用可接受的盐，已发现具有强效镇痛活性，含有这些化合物的制剂以药用剂量单位形式用于减轻温血动物的疼痛，以及使用这些制剂减轻动物疼痛的方法。还公开了制备这些化合物的方法。

  公开号：

  US04215114A1
• 作为产物：
  描述：

  5-hexenylazide 在 C₂₀H₂₈B₂FeN₈*C₆H₆ 作用下， 以 氘代苯 为溶剂， 反应 18.0h， 以83%的产率得到1-azabicyclo[4.1.0]heptane
  参考文献：
  名称：

  Synthesis of Fully Aliphatic Aziridines with a Macrocyclic Tetracarbene Iron Catalyst

  摘要：

  A second-generation aziridination catalyst supported by a borate-based dianionic macrocyclic tetracarbene ligand has been synthesized. The new macrocyclic tetracarbene iron(II) complex catalyzed the aziridination of alkyl azides and aliphatic alkenes showcasing the first fully aliphatic version of this C-2 + N-1 reaction. High isolated yields were obtained when no functional groups were present on the organic azides and alkenes, while modest yields were achieved when nonprotic functional groups were included. Even multiple functional groups can be added to the azide and alkene fragments to produce the most complex aziridines yet synthesized by this C-2 + N-1 catalytic reaction. The catalyst generated higher yields for aziridination with aryl azides and alkenes than the previously reported catalyst, [((TCPh)-T-Me,Et)Fe(NCCH3)(2)](PF6)(2). The contrast is particularly apparent with functionalized aryl azides where the second-generation catalyst now provides practical yields for synthetic chemistry. Finally, catalytic intramolecular aziridination was investigated since many natural products with aziridines feature bicyclic tertiary aziridines. For five- and six-membered rings, the bicyclic aziridines were formed catalytically, in contrast to previously studied catalyzed and uncatalyzed reactions.

  DOI：

  10.1021/acs.organomet.6b00066

文献信息

• Synthesis of Fully Aliphatic Aziridines with a Macrocyclic Tetracarbene Iron Catalyst
  作者：Preeti P. Chandrachud、Heather M. Bass、David M. Jenkins

  DOI：10.1021/acs.organomet.6b00066

  日期：2016.6.13

  A second-generation aziridination catalyst supported by a borate-based dianionic macrocyclic tetracarbene ligand has been synthesized. The new macrocyclic tetracarbene iron(II) complex catalyzed the aziridination of alkyl azides and aliphatic alkenes showcasing the first fully aliphatic version of this C-2 + N-1 reaction. High isolated yields were obtained when no functional groups were present on the organic azides and alkenes, while modest yields were achieved when nonprotic functional groups were included. Even multiple functional groups can be added to the azide and alkene fragments to produce the most complex aziridines yet synthesized by this C-2 + N-1 catalytic reaction. The catalyst generated higher yields for aziridination with aryl azides and alkenes than the previously reported catalyst, [((TCPh)-T-Me,Et)Fe(NCCH3)(2)](PF6)(2). The contrast is particularly apparent with functionalized aryl azides where the second-generation catalyst now provides practical yields for synthetic chemistry. Finally, catalytic intramolecular aziridination was investigated since many natural products with aziridines feature bicyclic tertiary aziridines. For five- and six-membered rings, the bicyclic aziridines were formed catalytically, in contrast to previously studied catalyzed and uncatalyzed reactions.
• Analgesic N-[2-(furyl-methylamino and 2-thienylmethylamino)cycloaliphatic]b
  申请人：The Upjohn Company

  公开号：US04215114A1

  公开（公告）日：1980-07-29

  Cis - and trans-N-(2-aminocycycloaliphatic)benzamide compounds of the formula ##STR1## e.g., N-methyl-N-[2-[(2-furylmethyl)methylamino]-cyclohexyl]-3,4-dichlorobenzami de, and their pharmaceutically acceptable salts, have been found to have potent analgesic activity, and compositions containing these compounds useful in pharmaceutical dosage unit form for alleviating pain in warm-blooded animals, as well as methods for alleviating pain in animals with these compositions. Processes for preparing the compounds are also disclosed.

  顺式和反式-N-(2-氨基环脂环烷基)苯甲酰胺化合物的化学式为##STR1## 例如，N-甲基-N-[2-[(2-呋喃甲基)甲基氨基]-环己基]-3,4-二氯苯甲酰胺，及其药用可接受的盐，已发现具有强效镇痛活性，含有这些化合物的制剂以药用剂量单位形式用于减轻温血动物的疼痛，以及使用这些制剂减轻动物疼痛的方法。还公开了制备这些化合物的方法。