(S)-N-benzoylproline anilide | 17360-31-5

• 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: (S)-N-benzoylproline anilide
• 英文别名: (S)-1-benzoyl-2-(phenylcarbamoyl)pyrrolidine；(2S)-1-benzoyl-N-phenylpyrrolidine-2-carboxamide
• CAS: 17360-31-5
• 化学式: C₁₈H₁₈N₂O₂
• 分子量: 294.353
• InChiKey: VJDJNFOZZRUJMG-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-N-benzoylproline anilide 在 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以80%的产率得到(S)-2-anilinomethyl-1-benzylpyrrolidine
  参考文献：
  名称：

  Enantioselective Addition of Diethylzinc to Aldehydes Catalyzed by (S)-1-Alkyl-2-(arylamino)methylpyrrolidine

  摘要：

  几种手性二胺，(S)-1-烷基-2-(芳基氨基)甲基吡咯烷，在二乙基锌对醛的对映选择性加成反应中作为手性催化剂。使用0.15当量的(S)-2-氨基甲基-1-苄基吡咯烷可以获得最佳结果，手性二级醇以高对映体过量（最高可达94% ee）获得。

  DOI：

  10.1246/bcsj.20120105
• 作为产物：
  描述：

  benzyl (2S)-2-(phenylcarbamoyl)pyrrolidine-1-carboxylate 在 吡啶 、 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 21.0h， 生成 (S)-N-benzoylproline anilide
  参考文献：
  名称：

  A simple proline-based organocatalyst for the enantioselective reduction of imines using trichlorosilane as a reductant

  摘要：

  A simple and inexpensive proline-based organocatalyst was developed for the reduction of imines using trichlorosilane as a reductant. The reduction of N-aryl imines in the presence of 10 mol % of N-pivaloyl-L-proline anilide was carried out to give the corresponding amines in excellent yields (up to 99%) with high enantioselectivities (up to 93% ee). (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.03.035

文献信息

• Amide Skeletal Elongation via Amino Acid Insertion
  作者：Zhengqiang Liu、Lei Zhou、Wenbo H. Liu

  DOI：10.1002/chem.202301729

  日期：2023.8.15

  A new amide bond activation paradigm through amino acid insertion enabled by two tandem intramolecular rearrangements is reported. This strategy only requires stable and readily available amide and amino acid as the starting materials, which does not need any pre-functionalization as well as the isolation of reaction intermediates.

  报道了一种通过两个串联分子内重排实现的氨基酸插入的新酰胺键激活范例。该策略仅需要稳定且易于获得的酰胺和氨基酸作为起始原料，不需要任何预官能化以及反应中间体的分离。
• Enantioselective Addition of Diethylzinc to Aldehydes Catalyzed by (<i>S</i>)-1-Alkyl-2-(arylamino)methylpyrrolidine
  作者：Naoya Hosoda、Hiroki Ito、Tatsuya Takimoto、Masatoshi Asami

  DOI：10.1246/bcsj.20120105

  日期：2012.9.15

  Several chiral diamines, (S)-1-alkyl-2-(arylamino)methylpyrrolidine, were used as chiral catalysts for the enantioselective addition of diethylzinc to aldehydes. The best results were obtained by employing 0.15 equiv of (S)-2-anilinomethyl-1-benzylpyrrolidine, and chiral secondary alcohols were obtained with high enantiomeric excesses (up to 94% ee).

  几种手性二胺，(S)-1-烷基-2-(芳基氨基)甲基吡咯烷，在二乙基锌对醛的对映选择性加成反应中作为手性催化剂。使用0.15当量的(S)-2-氨基甲基-1-苄基吡咯烷可以获得最佳结果，手性二级醇以高对映体过量（最高可达94% ee）获得。
• A simple proline-based organocatalyst for the enantioselective reduction of imines using trichlorosilane as a reductant
  作者：Takuya Kanemitsu、Atsushi Umehara、Rieko Haneji、Kazuhiro Nagata、Takashi Itoh

  DOI：10.1016/j.tet.2012.03.035

  日期：2012.5

  A simple and inexpensive proline-based organocatalyst was developed for the reduction of imines using trichlorosilane as a reductant. The reduction of N-aryl imines in the presence of 10 mol % of N-pivaloyl-L-proline anilide was carried out to give the corresponding amines in excellent yields (up to 99%) with high enantioselectivities (up to 93% ee). (C) 2012 Elsevier Ltd. All rights reserved.