6,6'-(piperazine-1,4-diyl)-bis(1a,5a,6β-bicyclo<3.1.0>hexan-3-one) | 155778-79-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂卓
• 英文名称: 6,6'-(piperazine-1,4-diyl)-bis(1a,5a,6β-bicyclo<3.1.0>hexan-3-one)
• CAS: 155778-79-3
• 化学式: C₁₆H₂₂N₂O₂
• 分子量: 274.363
• InChiKey: SHACQXPTUUIMIC-TYJIZLLCSA-N

物化性质

• 沸点：
  440.4±45.0 °C(predicted)
• 密度：
  1.346±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.56
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  40.62
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N-甲基哌嗪 、 6,6'-(piperazine-1,4-diyl)-bis(1a,5a,6β-bicyclo<3.1.0>hexan-3-one) 在 titanium(IV) isopropylate 、 sodium cyanoborohydride 作用下， 生成 1,4-bis-<1α,3β,5α,6β-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 、 sodium tetrahydroborate 、 N-氯代丁二酰亚胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 116.0h， 生成 6,6'-(piperazine-1,4-diyl)-bis(1a,5a,6β-bicyclo<3.1.0>hexan-3-one)
  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

文献信息

• Spatially fixed oligoamines IV. 1 flexibility and protonation of meander-type octamines
  作者：Rolf Wagemann、Elmar Vilsmaier、Gerhard Maas

  DOI：10.1016/0040-4020(95)00463-i

  日期：1995.8

  Meander-type octamines 6a and 6b possessing three piperazine units, two bicyclo[3.1.0]hexyl- and two azabicyclo[3.1.0]hexyl systems as building blocks, could be obtained by reductive amination of di(oxobicyclohexyl)piperazine 2 with piperazinyl-3azabicyclohexane derivatives 5a/b, respectively. The latter were synthesized from Nbenzylchloroenamine 11 and sodium borohydride and subsequent removal of

  具有三哌嗪单元，两个双环[3.1.0]己基和两个氮杂双环[3.1.0]己基体系作为结构单元的曲型八胺6a和6b可通过将二（氧代双环己基）哌嗪2与哌嗪基进行还原胺化反应而制得-3氮杂双环己烷衍生物5a / b。后者由N苄基氯亚胺11和硼氢化钠合成，随后除去苄基保护基。研究了新的低聚胺6a和6b的构象和分子柔性。由辛胺6b生成质子位置确定的二铵和四铵物种。使用二铵盐14 · 2 TFA的X射线结构分析来深入了解（氮杂双环己基）哌嗪三氟甲烷磺酸酯单元的分子排列。