(2S)-2,3-dibromopropyl N-([1,1'-biphenyl]-4-ylcarbonyl)-L-alaninate | 518315-61-2

• 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: (2S)-2,3-dibromopropyl N-([1,1'-biphenyl]-4-ylcarbonyl)-L-alaninate
• 英文别名: [(2S)-2,3-dibromopropyl] (2S)-2-[(4-phenylbenzoyl)amino]propanoate
• CAS: 518315-61-2
• 化学式: C₁₉H₁₉Br₂NO₃
• 分子量: 469.173
• InChiKey: JQSATADVMGJLGQ-SUMWQHHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  甲醇 、 (2S)-2,3-dibromopropyl N-([1,1'-biphenyl]-4-ylcarbonyl)-L-alaninate 在 乙酰氯 作用下， 反应 3.0h， 以95%的产率得到(2S)-2,3-dibromopropan-1-ol
  参考文献：
  名称：

  Crystallization-Induced Asymmetric Transformations. Enantiomerically pure (−)-(R)- and (+)-(S)-2,3-Dibromopropan-1-ol and Epibromohydrins. A Study of Dynamic Resolution via the Formation of Diastereoisomeric Esters

  摘要：

  (S)-2,3-Dibromopropan-1-ol of high enantiomer excess was obtained by crystallization-induced asymmetric transformations of racemic 2,3-dibromopropan-1-ol esterified with N-([1,1'-biphenyl]-4-ylcarbonyl-L-alanine; in particular, an asymmetric transformation of the first type (involving bromide exchange to equilibrate the diastereoisomeric esters) and an asymmetric transformation of the second type (involving a transesterification of diastereoisomeric esters with excess racemic alcohol) were devised.

  DOI：

  10.1002/1522-2675(200211)85:11<3785::aid-hlca3785>3.0.co;2-a
• 作为产物：
  描述：

  allyl N-([1,1'-biphenyl]-4-ylcarbonyl)-L-alaninate 在 溴 作用下， 以 氯仿 为溶剂， 反应 2.0h， 生成 (2S)-2,3-dibromopropyl N-([1,1'-biphenyl]-4-ylcarbonyl)-L-alaninate 、 (2R)-2,3-dibromopropyl N-([1,1'-biphenyl]-4-ylcarbonyl)-L-alaninate
  参考文献：
  名称：

  Crystallization-Induced Asymmetric Transformations. Enantiomerically pure (−)-(R)- and (+)-(S)-2,3-Dibromopropan-1-ol and Epibromohydrins. A Study of Dynamic Resolution via the Formation of Diastereoisomeric Esters

  摘要：

  (S)-2,3-Dibromopropan-1-ol of high enantiomer excess was obtained by crystallization-induced asymmetric transformations of racemic 2,3-dibromopropan-1-ol esterified with N-([1,1'-biphenyl]-4-ylcarbonyl-L-alanine; in particular, an asymmetric transformation of the first type (involving bromide exchange to equilibrate the diastereoisomeric esters) and an asymmetric transformation of the second type (involving a transesterification of diastereoisomeric esters with excess racemic alcohol) were devised.

  DOI：

  10.1002/1522-2675(200211)85:11<3785::aid-hlca3785>3.0.co;2-a

文献信息

• Crystallization-Induced Asymmetric Transformations. Enantiomerically pure (−)-(R)- and (+)-(S)-2,3-Dibromopropan-1-ol and Epibromohydrins. A Study of Dynamic Resolution via the Formation of Diastereoisomeric Esters
  作者：Gabriella Brunetto、Susanna Gori、Rita Fiaschi、Elio Napolitano

  DOI：10.1002/1522-2675(200211)85:11<3785::aid-hlca3785>3.0.co;2-a

  日期：2002.11

  (S)-2,3-Dibromopropan-1-ol of high enantiomer excess was obtained by crystallization-induced asymmetric transformations of racemic 2,3-dibromopropan-1-ol esterified with N-([1,1'-biphenyl]-4-ylcarbonyl-L-alanine; in particular, an asymmetric transformation of the first type (involving bromide exchange to equilibrate the diastereoisomeric esters) and an asymmetric transformation of the second type (involving a transesterification of diastereoisomeric esters with excess racemic alcohol) were devised.