(S)-4-Phenyl-N¹-((R)-1-phenyl-ethyl)-butane-1,2-diamine | 909408-59-9

• 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)-4-Phenyl-N¹-((R)-1-phenyl-ethyl)-butane-1,2-diamine
• 英文别名: (2S)-4-phenyl-1-N-[(1R)-1-phenylethyl]butane-1,2-diamine
• CAS: 909408-59-9
• 化学式: C₁₈H₂₄N₂
• 分子量: 268.402
• InChiKey: TWTURWGNIBAZQX-QAPCUYQASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  38
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-4-Phenyl-N¹-((R)-1-phenyl-ethyl)-butane-1,2-diamine 在 sodium tetrahydroborate 、 sodium cyanoborohydride 、 magnesium sulfate 作用下， 以 甲醇 为溶剂， 反应 20.5h， 生成 1-benzyl-2(R)-phenethyl-4-((R)-α-methylbenzyl)piperazine
  参考文献：
  名称：

  An efficient synthesis of chiral terminal 1,2-diamines using an enantiomerically pure [1-(1′R)-methylbenzyl]aziridine-2-yl]methanol

  摘要：

  Enantiomerically pure terminal 1,2-diamines, which can serve as precursors for the synthesis of many biologically important compounds, were synthesized efficiently from a commercially available chiral [1-(1'R)-methylbenzyl]aziridine-2-yl]methanol. Various enantiomerically pure 2-vinylaziridines were prepared by Wittig reactions from aziridine-2-carboxaldehyde and the corresponding phosphonium salts. The C(2)-N bond of the vinyl substituted aziridine ring was regioselectively cleaved by azidotrimethylsilane (TMSN3). The azido group and the double bond were reduced successively to give the target compounds in high yields. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.06.024
• 作为产物：
  描述：

  ((Z)-(S)-2-Azido-4-phenyl-but-3-enyl)-((R)-1-phenyl-ethyl)-amine 在 palladium on activated charcoal lithium aluminium tetrahydride 、 氢气 作用下， 以 甲醇 、 乙醚 为溶剂， 生成 (S)-4-Phenyl-N¹-((R)-1-phenyl-ethyl)-butane-1,2-diamine
  参考文献：
  名称：

  An efficient synthesis of chiral terminal 1,2-diamines using an enantiomerically pure [1-(1′R)-methylbenzyl]aziridine-2-yl]methanol

  摘要：

  Enantiomerically pure terminal 1,2-diamines, which can serve as precursors for the synthesis of many biologically important compounds, were synthesized efficiently from a commercially available chiral [1-(1'R)-methylbenzyl]aziridine-2-yl]methanol. Various enantiomerically pure 2-vinylaziridines were prepared by Wittig reactions from aziridine-2-carboxaldehyde and the corresponding phosphonium salts. The C(2)-N bond of the vinyl substituted aziridine ring was regioselectively cleaved by azidotrimethylsilane (TMSN3). The azido group and the double bond were reduced successively to give the target compounds in high yields. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.06.024

文献信息

• An efficient synthesis of chiral terminal 1,2-diamines using an enantiomerically pure [1-(1′R)-methylbenzyl]aziridine-2-yl]methanol
  作者：Baeck Kyoung Lee、Min Sung Kim、Heung Sik Hahm、Dong Sub Kim、Won Koo Lee、Hyun-Joon Ha

  DOI：10.1016/j.tet.2006.06.024

  日期：2006.8

  Enantiomerically pure terminal 1,2-diamines, which can serve as precursors for the synthesis of many biologically important compounds, were synthesized efficiently from a commercially available chiral [1-(1'R)-methylbenzyl]aziridine-2-yl]methanol. Various enantiomerically pure 2-vinylaziridines were prepared by Wittig reactions from aziridine-2-carboxaldehyde and the corresponding phosphonium salts. The C(2)-N bond of the vinyl substituted aziridine ring was regioselectively cleaved by azidotrimethylsilane (TMSN3). The azido group and the double bond were reduced successively to give the target compounds in high yields. (c) 2006 Elsevier Ltd. All rights reserved.