1,4-bis-(3-chloro-1,2,3,6-tetrahydro-1-methyl-pyridin-4-yl)-piperazine | 154233-59-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吖庚因类
• 英文名称: 1,4-bis-(3-chloro-1,2,3,6-tetrahydro-1-methyl-pyridin-4-yl)-piperazine
• 英文别名: 1,4-bis(3-chloro-1-methyl-3,6-dihydro-2H-pyridin-4-yl)piperazine
• CAS: 154233-59-7
• 化学式: C₁₆H₂₆Cl₂N₄
• 分子量: 345.315
• InChiKey: MXXOPVBVOJJLKT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.48
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  12.96
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1,4-bis-(3-chloro-1,2,3,6-tetrahydro-1-methyl-pyridin-4-yl)-piperazine 在 盐酸 、 sodium tetrahydroborate 作用下， 生成 6,6'-(piperazine-1,4-diyl)-bis<1α,5α,6β-3-methyl-3-azoniabicyclo<3.1.0>hexane>
  参考文献：
  名称：

  Functionalized chloroenamines in aminocyclopropane synthesis - XIII. Azaannulated cyclopropanes - rigid building blocks for oligoamines

  摘要：

  Oligoamines 5, 6 and 7 with rigid 3-azabicyclo[3.1.0]hexyl building blocks were synthesized from di(chloroenamines) 8 and nucleophiles. Sodium borohydride as nucleophile led to endo,endo-tetramines 5a,b; the same stereochemical result generating 5d and 5f was observed for cyanide or methyllithium as reagents. Methylmagnesium bromide reacted with 8 to give mainly exo,exo-tetramine 7f besides small amounts of isomers 5f and 6f. Basicity, conformation and molecular flexibility of the new tetramines 5 - 7 were studied. X-Ray structural analyses pointed out a meander shape of tetramine 5f and a linear arrangement of tetramine 7f.

  DOI：

  10.1016/s0040-4020(01)80788-2
• 作为产物：
  描述：

  N-甲基-4-哌啶酮 在 N-氯代丁二酰亚胺 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 13.0h， 生成 1,4-bis-(3-chloro-1,2,3,6-tetrahydro-1-methyl-pyridin-4-yl)-piperazine
  参考文献：
  名称：

  Functionalized chloroenamines in aminocyclopropane synthesis - XIII. Azaannulated cyclopropanes - rigid building blocks for oligoamines

  摘要：

  Oligoamines 5, 6 and 7 with rigid 3-azabicyclo[3.1.0]hexyl building blocks were synthesized from di(chloroenamines) 8 and nucleophiles. Sodium borohydride as nucleophile led to endo,endo-tetramines 5a,b; the same stereochemical result generating 5d and 5f was observed for cyanide or methyllithium as reagents. Methylmagnesium bromide reacted with 8 to give mainly exo,exo-tetramine 7f besides small amounts of isomers 5f and 6f. Basicity, conformation and molecular flexibility of the new tetramines 5 - 7 were studied. X-Ray structural analyses pointed out a meander shape of tetramine 5f and a linear arrangement of tetramine 7f.

  DOI：

  10.1016/s0040-4020(01)80788-2

文献信息

• Seibel Jens, Vilsmaier Elmar, Froehlich Karin, Maas Gerhard, Wagemann Rol+, Tetrahedron, 50 (1994) N 3, S 715-730
  作者：Seibel Jens, Vilsmaier Elmar, Froehlich Karin, Maas Gerhard, Wagemann Rol+

  DOI：——

  日期：——