(2S)-N-[(2R)-1-amino-1-oxo-3-phenylpropan-2-yl]pyrrolidine-2-carboxamide;2,2,2-trifluoroacetic acid | 1395873-62-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S)-N-[(2R)-1-amino-1-oxo-3-phenylpropan-2-yl]pyrrolidine-2-carboxamide;2,2,2-trifluoroacetic acid
• CAS: 1395873-62-7
• 化学式: C₂HF₃O₂*C₁₄H₁₉N₃O₂
• 分子量: 375.348
• InChiKey: HYQPWMGUWXWUTL-ZVWHLABXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.58
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  122
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  Fmoc-L-脯氨酸 、 Fmoc-D-苯丙氨酸 、 三氟乙酸 在 1-羟基苯并三唑 、 N,N'-二异丙基碳二亚胺 、 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 (2S)-N-[(2R)-1-amino-1-oxo-3-phenylpropan-2-yl]pyrrolidine-2-carboxamide;2,2,2-trifluoroacetic acid
  参考文献：
  名称：

  Effect of addition of Lewis/Brönsted acids in the asymmetric aldol condensation catalyzed by trifluoroacetate salts of proline-based dipeptides

  摘要：

  Proline-based dipeptides catalyze aldol condensations with good yield and stereoselectivity after addition of zinc or sodium acetate to the trifluoroacetate peptide. The chirality of the N-terminal proline in the catalyst determines the absolute configuration of the aldol product, but stereoselectivity depends on the configuration of both amino acids, and is higher for the enantiomeric pair R-S, S-R. Regarding the nature of the second component, optimal results in both yield and stereoselectivity are obtained when neutral unbranched primary amino acids are used. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.07.006
• 作为试剂：
  描述：

  2,6-二氯苯甲醛 、 丙酮 在 (2S)-N-[(2R)-1-amino-1-oxo-3-phenylpropan-2-yl]pyrrolidine-2-carboxamide;2,2,2-trifluoroacetic acid 、 zinc diacetate 作用下， 反应 120.0h， 生成 (4R)-4-(2,6-二氯苯基)-4-羟基丁烷-2-酮
  参考文献：
  名称：

  Effect of addition of Lewis/Brönsted acids in the asymmetric aldol condensation catalyzed by trifluoroacetate salts of proline-based dipeptides

  摘要：

  Proline-based dipeptides catalyze aldol condensations with good yield and stereoselectivity after addition of zinc or sodium acetate to the trifluoroacetate peptide. The chirality of the N-terminal proline in the catalyst determines the absolute configuration of the aldol product, but stereoselectivity depends on the configuration of both amino acids, and is higher for the enantiomeric pair R-S, S-R. Regarding the nature of the second component, optimal results in both yield and stereoselectivity are obtained when neutral unbranched primary amino acids are used. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.07.006

文献信息

• Effect of addition of Lewis/Brönsted acids in the asymmetric aldol condensation catalyzed by trifluoroacetate salts of proline-based dipeptides
  作者：Cecilia Andreu、Marcel·lí del Olmo、Gregorio Asensio

  DOI：10.1016/j.tet.2012.07.006

  日期：2012.9

  Proline-based dipeptides catalyze aldol condensations with good yield and stereoselectivity after addition of zinc or sodium acetate to the trifluoroacetate peptide. The chirality of the N-terminal proline in the catalyst determines the absolute configuration of the aldol product, but stereoselectivity depends on the configuration of both amino acids, and is higher for the enantiomeric pair R-S, S-R. Regarding the nature of the second component, optimal results in both yield and stereoselectivity are obtained when neutral unbranched primary amino acids are used. (C) 2012 Elsevier Ltd. All rights reserved.