(S)-2-tert-butoxycarbonylamino-4-benzylamino-1,1-diphenylbutane | 173914-64-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-2-tert-butoxycarbonylamino-4-benzylamino-1,1-diphenylbutane
• 英文别名: tert-butyl N-[(2S)-4-(benzylamino)-1,1-diphenylbutan-2-yl]carbamate
• CAS: 173914-64-2
• 化学式: C₂₈H₃₄N₂O₂
• 分子量: 430.59
• InChiKey: XNZDPFWDVJANLO-VWLOTQADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  50.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-2-tert-butoxycarbonylamino-4-benzylamino-1,1-diphenylbutane 在 palladium on activated charcoal 甲酸铵 作用下， 以 甲醇 为溶剂， 反应 8.0h， 以66%的产率得到(S)-3-tert-butoxycarbonylamino-4,4-diphenylbutylamine
  参考文献：
  名称：

  Synthesis of (S)-2-Amino-1,1-diphenylbutan-4-ol; conversion of an α-amino acid into an α-(diphenylmethyl) amine without loss of optical purity

  摘要：

  The title amino-alcohol 4 is an intermediate for the preparation of chiral bicyclic amidines and guanidines, and also for polyamines with potential as ligands in enantioselective catalysis. It has been synthesized from (S)-methionine 1 via (S)-homoserine lactone 2 and amino-diol 3. Hydrogenolysis of the doubly benzylic hydroxyl group in 3 proved non-trivial, but was eventually achieved through the application of catalytic transfer methodology to the bis-acetyl derivative 14.

  DOI：

  10.1016/0957-4166(95)00373-w
• 作为产物：
  描述：

  (S)-2-amino-1,1-diphenylbutan-4-ol 在 吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 11.0h， 生成 (S)-2-tert-butoxycarbonylamino-4-benzylamino-1,1-diphenylbutane
  参考文献：
  名称：

  Synthesis of (S)-2-Amino-1,1-diphenylbutan-4-ol; conversion of an α-amino acid into an α-(diphenylmethyl) amine without loss of optical purity

  摘要：

  The title amino-alcohol 4 is an intermediate for the preparation of chiral bicyclic amidines and guanidines, and also for polyamines with potential as ligands in enantioselective catalysis. It has been synthesized from (S)-methionine 1 via (S)-homoserine lactone 2 and amino-diol 3. Hydrogenolysis of the doubly benzylic hydroxyl group in 3 proved non-trivial, but was eventually achieved through the application of catalytic transfer methodology to the bis-acetyl derivative 14.

  DOI：

  10.1016/0957-4166(95)00373-w

文献信息

• Synthesis of (S)-2-Amino-1,1-diphenylbutan-4-ol; conversion of an α-amino acid into an α-(diphenylmethyl) amine without loss of optical purity
  作者：Peter H. Boyle、Anthony P. Davis、Kevin J. Dempsey、Gladys D. Hosken

  DOI：10.1016/0957-4166(95)00373-w

  日期：1995.11

  The title amino-alcohol 4 is an intermediate for the preparation of chiral bicyclic amidines and guanidines, and also for polyamines with potential as ligands in enantioselective catalysis. It has been synthesized from (S)-methionine 1 via (S)-homoserine lactone 2 and amino-diol 3. Hydrogenolysis of the doubly benzylic hydroxyl group in 3 proved non-trivial, but was eventually achieved through the application of catalytic transfer methodology to the bis-acetyl derivative 14.