tert-butyl N-[(1S)-2-phenyl-1-[(2R)-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-2-yl]ethyl]carbamate | 560216-06-0

• 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: tert-butyl N-[(1S)-2-phenyl-1-[(2R)-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-2-yl]ethyl]carbamate
• CAS: 560216-06-0
• 化学式: C₂₈H₃₁N₃O₂
• 分子量: 441.573
• InChiKey: HDYVSXPFFKAMOS-LOSJGSFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  62.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(1S)-2-phenyl-1-[(2R)-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-2-yl]ethyl]carbamate 在 sodium hydride 、 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 24.33h， 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
• 作为产物：
  描述：

  在 镍 一水合肼 、 zinc(II) chloride 作用下， 以 甲醇 为溶剂， 反应 26.0h， 生成 tert-butyl N-[(1S)-2-phenyl-1-[(2R)-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-2-yl]ethyl]carbamate
  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.