6,6'-(piperazine-1,4-diyl)-bis(1α,5α,6β-3-oxo-bicyclo<3.1.0>hexane-6-carbonitrile) | 155778-78-2

• 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: 6,6'-(piperazine-1,4-diyl)-bis(1α,5α,6β-3-oxo-bicyclo<3.1.0>hexane-6-carbonitrile)
• CAS: 155778-78-2
• 化学式: C₁₈H₂₀N₄O₂
• 分子量: 324.382
• InChiKey: WADKOAZTGAZRKO-TYTBLDAYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.35
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  88.2
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  6,6'-(piperazine-1,4-diyl)-bis(1α,5α,6β-3-oxo-bicyclo<3.1.0>hexane-6-carbonitrile) 在 titanium(IV) isopropylate 、 lithium aluminium tetrahydride 、 sodium cyanoborohydride 作用下， 以 乙醚 为溶剂， 反应 96.0h， 生成 1,4-bis-<1α,3β,5α,6β-6-aminomethyl-3-(4-methylpiperazin-1-yl)-bicyclo<3.1.0>hex-6-yl>-piperazine
  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：

  1,4-bis-(1,4-dioxaspiro<4,5>dec-7-en-8-yl)piperazine 在 盐酸 、 N-氯代丁二酰亚胺 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 61.0h， 生成 6,6'-(piperazine-1,4-diyl)-bis(1α,5α,6β-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