N-benzyl-N,N-bis<(S)-4,4-diphenyl-3-(1-pyrrolyl)-butyl>amine | 158530-71-3

• 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: N-benzyl-N,N-bis<(S)-4,4-diphenyl-3-(1-pyrrolyl)-butyl>amine
• 英文别名: Yvnqpxbkvsnwhv-gsvojqhpsa-；(3S)-N-benzyl-N-[(3S)-4,4-diphenyl-3-pyrrol-1-ylbutyl]-4,4-diphenyl-3-pyrrol-1-ylbutan-1-amine
• CAS: 158530-71-3
• 化学式: C₄₇H₄₇N₃
• 分子量: 653.91
• InChiKey: YVNQPXBKVSNWHV-GSVOJQHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.1
• 重原子数：
  50
• 可旋转键数：
  16
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-benzyl-N,N-bis<(S)-4,4-diphenyl-3-(1-pyrrolyl)-butyl>amine 在 palladium on activated charcoal 甲酸铵 作用下， 以 甲醇 为溶剂， 反应 2.5h， 以70%的产率得到Bis-((S)-4,4-diphenyl-3-pyrrol-1-yl-butyl)-amine
  参考文献：
  名称：

  Synthesis and investigation of a hindered, chiral, bicyclic guanidine

  摘要：

  Chiral amidines and guanidines have potential as enantioselective catalysts for reactions of nitroalkanes, through formation of hydrogen-bonded complexes with nitronate anions. With this in mind, the bicyclic guanidine 9 was synthesized from amino-alcohol 12, employing pyrrole formation as a protection method for the amino-nitrogen. Low enantioselectivities were obtained when 9 was used as catalyst for conjugate additions of nitroalkanes. However, other applications are suggested by its hindered, chiral and strongly basic nature.

  DOI：

  10.1016/0957-4166(95)00374-x
• 作为产物：
  描述：

  (S)-2-amino-1,1-diphenylbutan-4-ol 在 碳酸氢钠 、 溶剂黄146 、 甲基磺酰氯 作用下， 生成 N-benzyl-N,N-bis<(S)-4,4-diphenyl-3-(1-pyrrolyl)-butyl>amine
  参考文献：
  名称：

  (4S,8S)-4,8-bis(diphenylmethyl)-1,5,7-triazabicyclo[4,4,0]dec-5-ene; a hindered, chiral, bicyclic guanidine base with effective C 2-symmetry

  摘要：

  由L-蛋氨酸制备标题化合物5，并通过计算、核磁共振波谱等技术进行研究；结果表明，由于庞大的二苯甲基取代基的配置，5 的 N/NH 基团及其共轭酸占据了受阻的手性环境。

  DOI：

  10.1039/c39940001875

文献信息

• (4S,8S)-4,8-bis(diphenylmethyl)-1,5,7-triazabicyclo[4,4,0]dec-5-ene; a hindered, chiral, bicyclic guanidine base with effective C 2-symmetry
  作者：Peter H. Boyle、Anthony P. Davis、Kevin J. Dempsey、Gladys D. Hosken

  DOI：10.1039/c39940001875

  日期：——

  The title compound 5 is prepared from L-methionine and investigated by computational, NMR spectroscopic and other techniques; the results indicate that the N/NH groups of 5 and its conjugate acid occupy hindered, chiral environments due to the disposition of the bulky diphenylmethyl substituents.

  由L-蛋氨酸制备标题化合物5，并通过计算、核磁共振波谱等技术进行研究；结果表明，由于庞大的二苯甲基取代基的配置，5 的 N/NH 基团及其共轭酸占据了受阻的手性环境。
• Synthesis and investigation of a hindered, chiral, bicyclic guanidine
  作者：Anthony P. Davis、Kevin J. Dempsey

  DOI：10.1016/0957-4166(95)00374-x

  日期：1995.11

  Chiral amidines and guanidines have potential as enantioselective catalysts for reactions of nitroalkanes, through formation of hydrogen-bonded complexes with nitronate anions. With this in mind, the bicyclic guanidine 9 was synthesized from amino-alcohol 12, employing pyrrole formation as a protection method for the amino-nitrogen. Low enantioselectivities were obtained when 9 was used as catalyst for conjugate additions of nitroalkanes. However, other applications are suggested by its hindered, chiral and strongly basic nature.