2-[2-fluoro-2-(1-trityl-1H-imidazol-4-yl)-ethyl]isoindole-1,3-dione | 352695-81-9

• 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: 2-[2-fluoro-2-(1-trityl-1H-imidazol-4-yl)-ethyl]isoindole-1,3-dione
• 英文别名: 2-[2-Fluoro-2-(1-tritylimidazol-4-yl)ethyl]isoindole-1,3-dione
• CAS: 352695-81-9
• 化学式: C₃₂H₂₄FN₃O₂
• 分子量: 501.56
• InChiKey: JOBWCPBRKPCBSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  38
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  55.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[2-fluoro-2-(1-trityl-1H-imidazol-4-yl)-ethyl]isoindole-1,3-dione 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 3.5h， 生成 2-fluoro-2-(1-trityl-1H-imidazol-4-yl)ethylamine
  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：

  potassium phtalimide 、 4-(2-bromo-1-fluoroethyl)-1-trityl-1H-imidazole 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以49%的产率得到2-[2-fluoro-2-(1-trityl-1H-imidazol-4-yl)-ethyl]isoindole-1,3-dione
  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.