(S)-N-pivaloylproline anilide | 1308264-17-6

• 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-pivaloylproline anilide
• 英文别名: (S)-1-pivaloyl-2-(phenylcarbamoyl)pyrrolidine；(2S)-1-(2,2-dimethylpropanoyl)-N-phenylpyrrolidine-2-carboxamide
• CAS: 1308264-17-6
• 化学式: C₁₆H₂₂N₂O₂
• mdl: MFCD01305096
• 分子量: 274.363
• InChiKey: VBKOZLXLTIGOMA-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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-pivaloylproline 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67%的产率得到(S)-2-anilinomethyl-1-neopentylpyrrolidine
  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-pivaloylproline 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
• 作为试剂：
  描述：

  甲氧苯胺 、 对硝基苯乙酮 在 (S)-N-pivaloylproline anilide 、 三氯硅烷 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 36.0h， 生成 4-methoxy-N-(1-(4-nitrophenyl)ethyl)aniline 、 (R)-4-methoxy-N-(1-(4-nitrophenyl)ethyl)aniline
  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

• 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.