(2S,3S)-N,N-dibenzyl-3-chloromethyl-3,4-epoxy-1-phenylbutan-2-amine | 223727-88-6

• 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: (2S,3S)-N,N-dibenzyl-3-chloromethyl-3,4-epoxy-1-phenylbutan-2-amine
• 英文别名: (1S)-N,N-dibenzyl-1-[(2S)-2-(chloromethyl)oxiran-2-yl]-2-phenylethanamine
• CAS: 223727-88-6
• 化学式: C₂₅H₂₆ClNO
• 分子量: 391.941
• InChiKey: CLPHVUYFGPXYFZ-LOSJGSFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  15.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S,3S)-N,N-dibenzyl-3-chloromethyl-3,4-epoxy-1-phenylbutan-2-amine 在 lithium 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 生成 (S)-3-dibenzylamine-2-methylidene-4-phenylbutan-1-ol
  参考文献：
  名称：

  Preparation and Synthetic Applications of Enantiopure (2S,3S)- or (2R,3S)-2-Halomethyl-1,2-epoxyalkan-3-amines

  摘要：

  Enantiomerically pure (2S,3S)-3 and its diastereoisomer (2R,3S)-2-halomethyl-1,2-epoxyalkan-3-amine 4 have been obtained from 1-aminoalkyl halomethyl ketones 1 and (iodomethyl)lithium or (chloromethyl)lithium, respectively. Some synthetic applications of compounds 3 are described: chiral unsaturated 1,3-aminoalcohols 8 or 2-(halomethylidene)-3-(dibenzylamino)-alkan-1-ol 11 is obtained from 3 by halogeno-lithium or by hydrogen-lithium exchange, respectively. Transformation of 8c into its methyl ester derivative 9c is also reported.

  DOI：

  10.1021/jo9823590
• 作为产物：
  描述：

  二碘甲烷 、 (3S)-3-dibenzylamino-1-chloro-2-oxo-4-phenylbutane 在 甲基锂 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 以72%的产率得到(2S,3S)-N,N-dibenzyl-3-chloromethyl-3,4-epoxy-1-phenylbutan-2-amine
  参考文献：
  名称：

  Preparation and Synthetic Applications of Enantiopure (2S,3S)- or (2R,3S)-2-Halomethyl-1,2-epoxyalkan-3-amines

  摘要：

  Enantiomerically pure (2S,3S)-3 and its diastereoisomer (2R,3S)-2-halomethyl-1,2-epoxyalkan-3-amine 4 have been obtained from 1-aminoalkyl halomethyl ketones 1 and (iodomethyl)lithium or (chloromethyl)lithium, respectively. Some synthetic applications of compounds 3 are described: chiral unsaturated 1,3-aminoalcohols 8 or 2-(halomethylidene)-3-(dibenzylamino)-alkan-1-ol 11 is obtained from 3 by halogeno-lithium or by hydrogen-lithium exchange, respectively. Transformation of 8c into its methyl ester derivative 9c is also reported.

  DOI：

  10.1021/jo9823590