(2R,5S)-2-[(1S)-1-(tert-butoxycarbonyl)amino-2-phenylethyl]-5-phenyl-4-phenylcarbamoyl-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine

• 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: (2R,5S)-2-[(1S)-1-(tert-butoxycarbonyl)amino-2-phenylethyl]-5-phenyl-4-phenylcarbamoyl-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine
• 英文别名: tert-butyl N-[(1S)-2-phenyl-1-[(2R,5S)-5-phenyl-4-(phenylcarbamoyl)-1,2,3,5-tetrahydro-1,4-benzodiazepin-2-yl]ethyl]carbamate
• 化学式: C₃₅H₃₈N₄O₃
• 分子量: 562.712
• InChiKey: UCKOXCYUCGQPRY-QAXCHELISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  42
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  82.7
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-氨基二苯甲酮 在 镍 sodium hydride 、 一水合肼 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 38.33h， 生成 (2R,5S)-2-[(1S)-1-(tert-butoxycarbonyl)amino-2-phenylethyl]-5-phenyl-4-phenylcarbamoyl-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine
  参考文献：
  名称：

  Expedient One-Pot Synthesis of Novel Chiral 2-Substituted 5-Phenyl-1,4-benzodiazepine Scaffolds from Amino Acid-Derived Amino Nitriles

  摘要：

  An efficient and stereocontrolled synthesis of phenylalanine- and tryptophan-derived 5-phenyl-1,4-benzodiazepines is described. This new methodology involves, as a key step, the synthesis of 5-phenyl-2,3-dihydro-1H-1,4-benzodiazepines by a one-pot cyano reduction and reductive cyclization of the appropriate amino nitrile, which were obtained via a modified Strecker reaction of N-protected a-amino aldehydes with 2-aminobenzophenone and trimethylsilyl cyanide. The subsequent reduction of these 2,3dihydro-1H-1,4-benzodiazepines, followed by regioselective alkylation or acylation at position 4, led to 2,4-disubstituted-5-phenyl-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine.

  DOI：

  10.1021/jo034286c

文献信息

• Expedient One-Pot Synthesis of Novel Chiral 2-Substituted 5-Phenyl-1,4-benzodiazepine Scaffolds from Amino Acid-Derived Amino Nitriles
  作者：Susana Herrero、M. Teresa García-López、Rosario Herranz

  DOI：10.1021/jo034286c

  日期：2003.5.1

  An efficient and stereocontrolled synthesis of phenylalanine- and tryptophan-derived 5-phenyl-1,4-benzodiazepines is described. This new methodology involves, as a key step, the synthesis of 5-phenyl-2,3-dihydro-1H-1,4-benzodiazepines by a one-pot cyano reduction and reductive cyclization of the appropriate amino nitrile, which were obtained via a modified Strecker reaction of N-protected a-amino aldehydes with 2-aminobenzophenone and trimethylsilyl cyanide. The subsequent reduction of these 2,3dihydro-1H-1,4-benzodiazepines, followed by regioselective alkylation or acylation at position 4, led to 2,4-disubstituted-5-phenyl-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine.