20-Bromo-12,28-dithia-3,10,18,22,30,37-hexazaheptacyclo[37.3.1.118,22.03,11.04,9.029,37.031,36]tetratetraconta-1(42),4,6,8,10,20,29,31,33,35,39(43),40-dodecaene-19,44-dione | 1333467-57-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 20-Bromo-12,28-dithia-3,10,18,22,30,37-hexazaheptacyclo[37.3.1.118,22.03,11.04,9.029,37.031,36]tetratetraconta-1(42),4,6,8,10,20,29,31,33,35,39(43),40-dodecaene-19,44-dione
• 英文别名: 20-bromo-12,28-dithia-3,10,18,22,30,37-hexazaheptacyclo[37.3.1.118,22.03,11.04,9.029,37.031,36]tetratetraconta-1(42),4,6,8,10,20,29,31,33,35,39(43),40-dodecaene-19,44-dione
• CAS: 1333467-57-4
• 化学式: C₃₆H₃₇BrN₆O₂S₂
• 分子量: 729.765
• InChiKey: ANGVWTLRKLMXLW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  47
• 可旋转键数：
  0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  127
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1,3-bis[5-(benzimidazol-2-ylthio)pentyl]-5-bromouracil 、 间二溴苄 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以17%的产率得到20-Bromo-12,28-dithia-3,10,18,22,30,37-hexazaheptacyclo[37.3.1.118,22.03,11.04,9.029,37.031,36]tetratetraconta-1(42),4,6,8,10,20,29,31,33,35,39(43),40-dodecaene-19,44-dione
  参考文献：
  名称：

  Synthesis and reactivity of acyclic and macrocyclic uracils bridged with five-membered heterocycles

  摘要：

  Replacement of terminal atoms of Br in 1,3-bis(bromopentyl)-5(6)-substituted uracils with 2-mercapto-5-methyl-1,3,4-thiadiazole, 2,5-dimercapto-1,3,4-thiadiazole, 2-mercaptoimidazole, and 2-mercaptobenzimidazoles resulted in a series of acyclic compounds and isomeric heterocyclophanes. Structures of macrocyclic regioisomers were unambiguously determined by NMR data. One of the regioisomers exhibits a hypochromic effect with respect to model compounds. The acyclic uracils obtained bridged with five-membered heterocycles are alkylated with methyliodide and methyl tosylate, and oxidated with m-CPBA. H2O2, and I-2. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.07.034

文献信息

• Synthesis and reactivity of acyclic and macrocyclic uracils bridged with five-membered heterocycles
  作者：Vyacheslav E. Semenov、Evgeniya S. Krylova、Irina V. Galyametdinova、Alla V. Chernova、Sergey V. Kharlamov、Shamil K. Latypov、Vladimir S. Reznik

  DOI：10.1016/j.tet.2011.07.034

  日期：2011.9

  Replacement of terminal atoms of Br in 1,3-bis(bromopentyl)-5(6)-substituted uracils with 2-mercapto-5-methyl-1,3,4-thiadiazole, 2,5-dimercapto-1,3,4-thiadiazole, 2-mercaptoimidazole, and 2-mercaptobenzimidazoles resulted in a series of acyclic compounds and isomeric heterocyclophanes. Structures of macrocyclic regioisomers were unambiguously determined by NMR data. One of the regioisomers exhibits a hypochromic effect with respect to model compounds. The acyclic uracils obtained bridged with five-membered heterocycles are alkylated with methyliodide and methyl tosylate, and oxidated with m-CPBA. H2O2, and I-2. (C) 2011 Elsevier Ltd. All rights reserved.