benzyl (S)-2-[(pyrrolidin-1-yl)methyl]pyrrolidine-1-carboxylate | 134591-58-5

• 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: benzyl (S)-2-[(pyrrolidin-1-yl)methyl]pyrrolidine-1-carboxylate
• 英文别名: (S)-benzyl-2-(pyrrolidin-1-ylmethyl)pyrrolidine-1-carboxylate；(S)-Benzyl 2-(pyrrolidin-1-ylmethyl)pyrrolidine-1-carboxylate；benzyl (2S)-2-(pyrrolidin-1-ylmethyl)pyrrolidine-1-carboxylate
• CAS: 134591-58-5
• 化学式: C₁₇H₂₄N₂O₂
• 分子量: 288.39
• InChiKey: JXLXDVBJLMHKSG-INIZCTEOSA-N

物化性质

• 沸点：
  411.0±28.0 °C(Predicted)
• 密度：
  1.146±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  32.8
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  benzyl (S)-2-[(pyrrolidin-1-yl)methyl]pyrrolidine-1-carboxylate 、 硫酸二甲酯 在 5%-palladium/activated carbon 、 氢气 作用下， 以 二氯甲烷 、 甲醇 为溶剂， 20.0 ℃ 、400.01 kPa 条件下， 反应 0.83h， 以97%的产率得到(S)-1-methyl-1-[(pyrrolidin-2-yl)methyl]pyrrolidin-1-ium methyl sulfate
  参考文献：
  名称：

  Basic chiral ionic liquids: A novel strategy for acid-free organocatalysis

  摘要：

  We present design, synthesis and application of basic chiral ionic liquids based on commercially available (S)-proline. This new set of chiral ionic liquids was specifically designed to replace trifluoroacetic acid in enamine-based organocatalysis for asymmetric C-C bond formation. Based on their permanent charge, these chiral ionic liquids could be applied as organocatalysts in asymmetric aldol reaction of 4-nitrobenzaldehyde and acetone, and good yields and selectivities up to 80%ee could be obtained without additional acid. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cattod.2012.07.002
• 作为产物：
  描述：

  N-苄氧羰基-L-脯氨酸 在 bis(2-chlorophenyl)borinic acid 、 苯硅烷 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.5h， 生成 benzyl (S)-2-[(pyrrolidin-1-yl)methyl]pyrrolidine-1-carboxylate
  参考文献：
  名称：

  硼酸催化氢化硅烷还原叔酰胺：胺的轻度和化学选择性合成

  摘要：

  据报道，由硼酸催化的各种芳基，烷基和α，β-不饱和酰胺与苯基硅烷的还原反应。前所未有的反应是在非常温和的条件下进行的，并生成了有用的胺。此外，该反应可耐受多种官能团。初步研究表明，中间体二芳基氢硼烷参与了反应机理。

  DOI：

  10.1002/chem.201604802

文献信息

• Basic chiral ionic liquids: A novel strategy for acid-free organocatalysis
  作者：Maria Vasiloiu、Daniel Rainer、Peter Gaertner、Christian Reichel、Christian Schröder、Katharina Bica

  DOI：10.1016/j.cattod.2012.07.002

  日期：2013.2

  We present design, synthesis and application of basic chiral ionic liquids based on commercially available (S)-proline. This new set of chiral ionic liquids was specifically designed to replace trifluoroacetic acid in enamine-based organocatalysis for asymmetric C-C bond formation. Based on their permanent charge, these chiral ionic liquids could be applied as organocatalysts in asymmetric aldol reaction of 4-nitrobenzaldehyde and acetone, and good yields and selectivities up to 80%ee could be obtained without additional acid. (C) 2012 Elsevier B.V. All rights reserved.
• Borinic Acid Catalysed Reduction of Tertiary Amides with Hydrosilanes: A Mild and Chemoselective Synthesis of Amines
  作者：Aurélien Chardon、Tharwat Mohy El Dine、Rémi Legay、Michaël De Paolis、Jacques Rouden、Jérôme Blanchet

  DOI：10.1002/chem.201604802

  日期：2017.2.10

  A reduction of various aryl, alkyl, and α,β‐unsaturated amides with phenylsilane, catalysed by a borinic acid, is reported. The unprecedented reaction was carried out under very mild conditions and led to useful amines. Furthermore, the reaction tolerates a variety of functional groups. Initial investigations implicated that an intermediate diarylhydroborane is involved in the reaction mechanism.

  据报道，由硼酸催化的各种芳基，烷基和α，β-不饱和酰胺与苯基硅烷的还原反应。前所未有的反应是在非常温和的条件下进行的，并生成了有用的胺。此外，该反应可耐受多种官能团。初步研究表明，中间体二芳基氢硼烷参与了反应机理。