1α,5α,6β-6-(4-benzyl-piperazin-1-yl)-3-oxo-bicyclo<3.1.0>hexane-6-carbonitrile | 155778-90-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1α,5α,6β-6-(4-benzyl-piperazin-1-yl)-3-oxo-bicyclo<3.1.0>hexane-6-carbonitrile
• CAS: 155778-90-8
• 化学式: C₁₈H₂₁N₃O
• 分子量: 295.384
• InChiKey: OHMKBUSMRBNZGV-BCDXTJNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.68
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  47.34
• 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,6β-6-(4-benzyl-piperazin-1-yl)-3-oxo-bicyclo<3.1.0>hexane-6-carbonitrile 在 palladium on activated charcoal titanium(IV) isopropylate 、 氢气 、 sodium cyanoborohydride 、 对甲苯磺酸 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 131.0h， 生成 1α,3β,5α,6β-3-(4-methylpiperazin-1-yl)-6-<4-<4-(4-methylpiperazin-1-yl)-cyclohex-1-en-1-yl>-piperazin-1-yl>-bicyclo<3.1.0>hexane-6-carbonitrile
  参考文献：
  名称：

  Functionalized chloroenamines in aminocyclopropane synthesis - XIV. Aminoannulated cyclopropanes - rigid building blocks for oligoamines

  摘要：

  Sterically pure meander oligoamines 5 possessing bicyclo[3.1.0]hexyl moieties as rigid building blocks were synthesized from monoketal 9 via di(chloroenamine) 14, bicyclic diketones 16 and subsequent reductive amination of 16. Use of the same reactions and change of the sequence of the steps led to hexamine 6a, a diastereomer of 5a. Hexamine 7a, a third diastereomer of 5a, was obtained with definite stereochemistry by a multistep approach starting from monoketal 9, too. X-Ray analysis of hexamine 5a, determination of basicity and studies of conformation and of molecular flexibility gave an insight in structural properties of the new type of meander oligoamines 5.

  DOI：

  10.1016/s0040-4020(01)80789-4
• 作为产物：
  描述：

  1α,5α,6β-6-(4-benzyl-piperazin-1-yl)-spirohexane-3,2'-1'3'-dioxolane>-6-carbonitrile 在 盐酸 作用下， 以 氯仿 为溶剂， 反应 2.0h， 以70%的产率得到1α,5α,6β-6-(4-benzyl-piperazin-1-yl)-3-oxo-bicyclo<3.1.0>hexane-6-carbonitrile
  参考文献：
  名称：

  Functionalized chloroenamines in aminocyclopropane synthesis - XIV. Aminoannulated cyclopropanes - rigid building blocks for oligoamines

  摘要：

  Sterically pure meander oligoamines 5 possessing bicyclo[3.1.0]hexyl moieties as rigid building blocks were synthesized from monoketal 9 via di(chloroenamine) 14, bicyclic diketones 16 and subsequent reductive amination of 16. Use of the same reactions and change of the sequence of the steps led to hexamine 6a, a diastereomer of 5a. Hexamine 7a, a third diastereomer of 5a, was obtained with definite stereochemistry by a multistep approach starting from monoketal 9, too. X-Ray analysis of hexamine 5a, determination of basicity and studies of conformation and of molecular flexibility gave an insight in structural properties of the new type of meander oligoamines 5.

  DOI：

  10.1016/s0040-4020(01)80789-4