4-(2-bromo-1-fluoroethyl)-1-trityl-1H-imidazole | 352695-71-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 4-(2-bromo-1-fluoroethyl)-1-trityl-1H-imidazole
• 英文别名: 4-(2-Bromo-1-fluoroethyl)-1-tritylimidazole
• CAS: 352695-71-7
• 化学式: C₂₄H₂₀BrFN₂
• 分子量: 435.339
• InChiKey: JLUWLRJGWBRSCJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(2-bromo-1-fluoroethyl)-1-trityl-1H-imidazole 在 palladium on activated charcoal sodium azide 、 氢气 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 100.0 ℃ 、276.01 kPa 条件下， 反应 24.0h， 生成 2-(1-三苯甲游基-1H-咪唑-4-基)-乙胺水合物
  参考文献：
  名称：

  New Building Blocks for Fluorinated Imidazole Derivatives:  Preparation of β-Fluoro- and β,β-Difluorohistamine

  摘要：

  We demonstrate that "FBr" addition to 1-trityl-4-vinyl-1H-imidazole (7) provides a convenient route to side-chain-fluorinated histamines. Thus, addition of "FBr" to the double bond of 7 occurs with Markovnikov regioselectivity to produce 4-(2-bromo-1-fluoroethyl)-1-trityl-1H-imidazole (8). Substitution with azide, reduction, and removal of the trityl group provide beta -fluorohistamine (1) as the dihydrochloride. Elimination of HBr from 8 followed by a second addition of "FBr" gives 4-(2-bromo-1,1-difluoroethyl)-1-trityl-1H-imidazole (15). This was similarly converted to beta,beta -difluorohistamine (2) as the dihydrochloride.

  DOI：

  10.1021/jo0102415
• 作为产物：
  描述：

  N-溴代丁二酰亚胺(NBS) 、 1-triphenylmethyl-4-vinylimidazole 在 triethylamine tris(hydrogen fluoride) 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以74%的产率得到4-(2-bromo-1-fluoroethyl)-1-trityl-1H-imidazole
  参考文献：
  名称：

  New Building Blocks for Fluorinated Imidazole Derivatives:  Preparation of β-Fluoro- and β,β-Difluorohistamine

  摘要：

  We demonstrate that "FBr" addition to 1-trityl-4-vinyl-1H-imidazole (7) provides a convenient route to side-chain-fluorinated histamines. Thus, addition of "FBr" to the double bond of 7 occurs with Markovnikov regioselectivity to produce 4-(2-bromo-1-fluoroethyl)-1-trityl-1H-imidazole (8). Substitution with azide, reduction, and removal of the trityl group provide beta -fluorohistamine (1) as the dihydrochloride. Elimination of HBr from 8 followed by a second addition of "FBr" gives 4-(2-bromo-1,1-difluoroethyl)-1-trityl-1H-imidazole (15). This was similarly converted to beta,beta -difluorohistamine (2) as the dihydrochloride.

  DOI：

  10.1021/jo0102415

文献信息

• New Building Blocks for Fluorinated Imidazole Derivatives:  Preparation of β-Fluoro- and β,β-Difluorohistamine
  作者：Bohumil Dolensky、Kenneth L. Kirk

  DOI：10.1021/jo0102415

  日期：2001.6.1

  We demonstrate that "FBr" addition to 1-trityl-4-vinyl-1H-imidazole (7) provides a convenient route to side-chain-fluorinated histamines. Thus, addition of "FBr" to the double bond of 7 occurs with Markovnikov regioselectivity to produce 4-(2-bromo-1-fluoroethyl)-1-trityl-1H-imidazole (8). Substitution with azide, reduction, and removal of the trityl group provide beta -fluorohistamine (1) as the dihydrochloride. Elimination of HBr from 8 followed by a second addition of "FBr" gives 4-(2-bromo-1,1-difluoroethyl)-1-trityl-1H-imidazole (15). This was similarly converted to beta,beta -difluorohistamine (2) as the dihydrochloride.