1α,5α,6α-6-morpholino-3-oxobicyclo<3.1.0>hexane-6-carbonitrile | 172586-99-1

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 1α,5α,6α-6-morpholino-3-oxobicyclo<3.1.0>hexane-6-carbonitrile
• CAS: 172586-99-1
• 化学式: C₁₁H₁₄N₂O₂
• 分子量: 206.244
• InChiKey: PRLUVBKMOZPXQU-URLYPYJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.19
• 重原子数：
  15.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  53.33
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1α,5α,6α-6-morpholino-3-oxobicyclo<3.1.0>hexane-6-carbonitrile 在 10% palladium on active carbon 氢气 、 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 甲醇 、 1,2-二氯乙烷 为溶剂， 反应 24.0h， 生成 3-amino-4-morpholino-2-azatricyclo[3.2.1.0^4,6]oct-2-ene
  参考文献：
  名称：

  Morpholino-azahomotricyclanimines–morpholine derivatives with a bulky cage-type substituent

  摘要：

  Reductive amination of bicyclic cyanoketone 3 with benzylamine 5a provided morpholino-azahomotricyclanimine 6a. The crystal structure of cage compound 6a is reported. The dynamics of morpholine in 6a, in the debenzylated product 6b/8 and in the amidinium salt 7a were investigated and compared with those in a bicyclic amidino analogue 14. The different and partial unexpected results were interpreted by studying the cyclopropane-morpholine rotation in 6b and 14 by molecular modeling and the C(2)-amino rotation in aminoacetamidine 15 by ab initio calculation. (C) 1999 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-2860(99)00108-8
• 作为产物：
  描述：

  4-(7,9-dichloro-1,4-dioxaspiro<4.5>dec-7-en-8-yl)-morpholine 在 盐酸 、 sodium 作用下， 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 反应 77.0h， 生成 1α,5α,6α-6-morpholino-3-oxobicyclo<3.1.0>hexane-6-carbonitrile
  参考文献：
  名称：

  The ensemble of 3,6-diaminobicyclo[3.1.0]hexanecarbonitrile diastereomers — Constrained analogues of conformers of cyclohexane-1,4-diamine species

  摘要：

  Dimorpholinobicyclo[3.1.0]hexanecarbonitrile diastereomers la and 8a have been synthesized with high stereoselectivity starting from dichloroenamines 11 and 13. The sequence 11 --> 17 --> 19 and reductive amination of the latter provided isomer la. Ring closure of 13 by cyanide and subsequent dechlorination of 14 produced compound 8a. The stereochemistry of the cyclopropane forming reaction was studied using cis and trans isomers of chloroenamine 12: trans 12-t gave almost exclusively 3 alpha-morpholine derivatives 4a / 8a upon interaction of cyanide. Cis 12-c led to 3 alpha- and 3 beta-morpholine products 4a / 8a and 1a / 5a in a ratio of 3:1 indicating an aminoallylcation intermediate 30 in the former case. Cis-configuration of chloroenamine isomer 12-c was established by X-ray structural analysis.

  DOI：

  10.1016/0040-4020(95)00682-x