(2R,3S)-3-(Dibenzylamino)-1-chloro-4-phenylbutan-2-ol | 171962-76-8

• 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: (2R,3S)-3-(Dibenzylamino)-1-chloro-4-phenylbutan-2-ol
• 英文别名: (2R,3S)-3-dibenzylamino-1-chloro-2-hydroxy-4-phenylbutane；(2R,3S)-1-chloro-3-(dibenzylamino)-4-phenylbutan-2-ol
• CAS: 171962-76-8
• 化学式: C₂₄H₂₆ClNO
• 分子量: 379.93
• InChiKey: ZPDFBVPCJFAPFI-ZEQRLZLVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R,3S)-3-(Dibenzylamino)-1-chloro-4-phenylbutan-2-ol 在 硫酸 作用下， 以 二氯甲烷 为溶剂， 以76%的产率得到(2R,3S)-1-chloro-3-dibenzylamino-4-phenyl-2-butanol sulfuric acid salt
  参考文献：
  名称：

  Production method of aminochlorohydrin sulfate

  摘要：

  (2R,3S)-3-tert-butoxycarbonylamino-1-chloro-2-hydroxy-4-phenylbutane或(2S,3R)-3-tert-butoxycarbonylamino-1-chloro-2-hydroxy-4-phenylbutane可以通过以下步骤方便地高产率地制备：(a)将化合物(1)与氯甲基锂反应，得到化合物(2)和至少一种副产物；(b)将化合物(2)和副产物溶解在极性溶剂中，并向溶液中加入水，使化合物(2)以晶体形式沉淀出来；(c)将化合物(2)的晶体还原，得到化合物(3)和至少其对映异构体作为杂质；(d)加入硫酸至其中，得到化合物(4)和至少其对映异构体作为杂质；(e)从含有乙酸酯或乙酸酯的溶液中沉淀化合物(4)为晶体。

  公开号：

  EP1777213A1
• 作为产物：
  描述：

  (2S)-2-氨基-3-苯丙酸乙酯 在 lithium aluminium tetrahydride 、 甲基锂 、 N,N-二异丙基乙胺 、 lithium bromide 作用下， 以 四氢呋喃 、 乙醚 、 氯仿 为溶剂， 反应 11.5h， 生成 (2R,3S)-3-(Dibenzylamino)-1-chloro-4-phenylbutan-2-ol
  参考文献：
  名称：

  High Diastereoselective Synthesis of Threo or Erythro Aminoalkyl Epoxides from .alpha.-Amino Acids

  摘要：

  alpha-Chloro-alpha'-(dibenzylamino) methylketones 3 are synthesized in enantiomerically pure form starting from alpha-amino acids. Reduction of amino ketones 3 and further epoxidation affords three aminoalkyl epoxides 6 with diastereoisomeric excess ranging between 94% and 98%. The synthesis of erythro amino epoxides 9 is also described by reaction of alpha-amino aldehydes 7 with in situ generated (halomethyl)lithium. Amino epoxides 9 were obtained with a diastereoisomeric excess ranging between 91% and 98%.

  DOI：

  10.1021/jo00126a019

文献信息

• High Diastereoselective Synthesis of Threo or Erythro Aminoalkyl Epoxides from .alpha.-Amino Acids
  作者：Jose Barluenga、Beatriz Baragana、Jose M. Concellon

  DOI：10.1021/jo00126a019

  日期：1995.10

  alpha-Chloro-alpha'-(dibenzylamino) methylketones 3 are synthesized in enantiomerically pure form starting from alpha-amino acids. Reduction of amino ketones 3 and further epoxidation affords three aminoalkyl epoxides 6 with diastereoisomeric excess ranging between 94% and 98%. The synthesis of erythro amino epoxides 9 is also described by reaction of alpha-amino aldehydes 7 with in situ generated (halomethyl)lithium. Amino epoxides 9 were obtained with a diastereoisomeric excess ranging between 91% and 98%.
• Production method of aminochlorohydrin sulfate
  申请人：Ajinomoto Co., Inc.

  公开号：EP1777213A1

  公开（公告）日：2007-04-25

  Highly pure (2R,3S)-3-tert-butoxycarbonylamino-1-chloro-2-hydroxy-4-phenylbutane or (2S,3R)-3-tert-butoxycarbonylamino-1-chloro-2-hydroxy-4-phenylbutane may be conveniently produced in high yield by: (a) reacting compound (1) with lithiumchloromethane to give compound (2) and at least a byproduct; (b) dissolving compound (2) and the byproduct in a polar solvent and adding water to the solution to precipitate compound (2) as crystals; (c) reducing the crystals of compound (2) to give compound (3) and at least its diastereomer as an impurity; (d) adding sulfuric acid thereto to give compound (4) and at least its diastereomer as an impurity; and (e) precipitating compound (4) as crystals from a solution containing acetic acid ester or acetic acid ester.

  (2R,3S)-3-tert-butoxycarbonylamino-1-chloro-2-hydroxy-4-phenylbutane或(2S,3R)-3-tert-butoxycarbonylamino-1-chloro-2-hydroxy-4-phenylbutane可以通过以下步骤方便地高产率地制备：(a)将化合物(1)与氯甲基锂反应，得到化合物(2)和至少一种副产物；(b)将化合物(2)和副产物溶解在极性溶剂中，并向溶液中加入水，使化合物(2)以晶体形式沉淀出来；(c)将化合物(2)的晶体还原，得到化合物(3)和至少其对映异构体作为杂质；(d)加入硫酸至其中，得到化合物(4)和至少其对映异构体作为杂质；(e)从含有乙酸酯或乙酸酯的溶液中沉淀化合物(4)为晶体。