(+/-)-Tifluadom hydrochloride | 96337-50-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯二氮卓类
• 英文名称: (+/-)-Tifluadom hydrochloride
• 英文别名: 1-methyl-2-[(thiophene-3-carbonyl)-aminomethyl]-5-(2-fluorophenyl)-1H-2,3-dihydro-1,4-benzodiazepine (hydrochloride)；Tifluadom Hydrochloride；N-[[5-(2-fluorophenyl)-1-methyl-2,3-dihydro-1,4-benzodiazepin-2-yl]methyl]thiophene-3-carboxamide;hydrochloride
• CAS: 96337-50-7
• 化学式: C₂₂H₂₀FN₃OS*ClH
• 分子量: 429.946
• InChiKey: JFZSUQQSHDYRGA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.39
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  72.9
• 氢给体数：
  2
• 氢受体数：
  5

制备方法与用途

用途

Tifluadom，一种κ-阿片受体激动剂和胆囊收缩素-A（CCK-A）受体拮抗剂，被用作模型来制备一系列2-(氨基甲基)-和3-(氨基甲基)-1,4-苯并二氮杂芑衍生物。

反应信息

• 作为反应物：
  描述：

  (+/-)-Tifluadom hydrochloride 生成 Thiophene-3-carboxylic acid [(S)-5-(2-fluoro-phenyl)-1-methyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-2-ylmethyl]-amide; hydrochloride
  参考文献：
  名称：

  (−)-(2S)-Tifluadom Hydrochloride and Two of its (−)-(2S)-2-(Acylaminomethyl)benzodiazepine Hydrochloride Analogues

  摘要：

  The structures of three (-)-(2S)-(acyraminomethyl)-benzodiazepine hydrochlorides, namely, 5-(2-fluorophenyl)-1-methyl-2-(3-thenoylaminomethyl)-2,3-dihydro-1H-1,4-benzodiazepin-4-ium chloride [C22H21FN3OS+.-Cl-, (1), tifluadom], 1,7-dimethyl-5-phenyl-2-(3-thenoylaminomethyl)-2,3-dihydro-1H-l,4-benzodiazepin-4-ium chloride [C23H24N3OS+.Cl-, (2)] and 5-(4-fluorophenyl)-1, 8-dimethyl-2-(p-toluoylaminomethyl)-2, 3-dihydro-1H-1,4-benzodiazepin-4-ium chloride hemi(isobutyl methyl ketone) solvate [C26H27FN3O+.Cl-.-0.5C(6)H(12)O, (3)] are reported. The conformations of the molecules are very similar. The seven-membered ring has a conformation halfway between a distorted boat and a distorted sofa, with the 2-substituent in a flagpole orientation and the acylaminomethyl moiety in an extended conformation.

  DOI：

  10.1107/s0108270198003412

文献信息

• (−)-(2<i>S</i>)-Tifluadom Hydrochloride and Two of its (−)-(2<i>S</i>)-2-(Acylaminomethyl)benzodiazepine Hydrochloride Analogues
  作者：O. M. Peeters、R. L. Meurisse、N. M. Blaton、C. J. De Ranter

  DOI：10.1107/s0108270198003412

  日期：1998.8.15

  The structures of three (-)-(2S)-(acyraminomethyl)-benzodiazepine hydrochlorides, namely, 5-(2-fluorophenyl)-1-methyl-2-(3-thenoylaminomethyl)-2,3-dihydro-1H-1,4-benzodiazepin-4-ium chloride [C22H21FN3OS+.-Cl-, (1), tifluadom], 1,7-dimethyl-5-phenyl-2-(3-thenoylaminomethyl)-2,3-dihydro-1H-l,4-benzodiazepin-4-ium chloride [C23H24N3OS+.Cl-, (2)] and 5-(4-fluorophenyl)-1, 8-dimethyl-2-(p-toluoylaminomethyl)-2, 3-dihydro-1H-1,4-benzodiazepin-4-ium chloride hemi(isobutyl methyl ketone) solvate [C26H27FN3O+.Cl-.-0.5C(6)H(12)O, (3)] are reported. The conformations of the molecules are very similar. The seven-membered ring has a conformation halfway between a distorted boat and a distorted sofa, with the 2-substituent in a flagpole orientation and the acylaminomethyl moiety in an extended conformation.