(2S,2'S)-1,1'-(5-methyl-1,3-phenylene)bis(methylene)dipyrrolidine-2-carboxylic acid | 1187086-51-6

• 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: (2S,2'S)-1,1'-(5-methyl-1,3-phenylene)bis(methylene)dipyrrolidine-2-carboxylic acid
• 英文别名: (2S)-1-[[3-[[(2S)-2-carboxypyrrolidin-1-yl]methyl]-5-methylphenyl]methyl]pyrrolidine-2-carboxylic acid
• CAS: 1187086-51-6
• 化学式: C₁₉H₂₆N₂O₄
• 分子量: 346.426
• InChiKey: VFSBQSFJXQBZCO-IRXDYDNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  81.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  甲醇 、 (2S,2'S)-1,1'-(5-methyl-1,3-phenylene)bis(methylene)dipyrrolidine-2-carboxylic acid 在 氯化亚砜 作用下， 生成 dimethyl (2S,2'S)-1,1'-(5-methyl-1,3-phenylene)bis(methylene)dipyrrolidine-2-carboxylate hydrochloride
  参考文献：
  名称：

  Enantioselective Nucleophilic Addition of Trimethylsilylacetylene to N-Phosphinoylimines Promoted by C₂-Symmetric Proline-Derived β-Amino Alcohol

  摘要：

  Both C-2- and C-3-symmetric proline-derived beta-amine alcohol ligands were designed, synthesized, and successfully applied to the enantioselective direct addition of trimethylsilylacetylene to N-phosphinoylimines. Aromatic, heteroaromatic, and aliphatic N-(diphenylphosphinoyl) imines and several N-(diethoxyphosphoryl) imines were tested, and optically active propargylic amides in good yields (up to 92%) and excellent enantioselectivities (up to 95%) were obtained by the simple experimental procedure. The convenience, mild conditions, and easy deprotection of the phosphonamide products made the present method very attractive. Furthermore, the Michael-type addition process of C=N alkynylation was studied and proposed on the basis of React P-31 NMR investigation.

  DOI：

  10.1021/jo901492w
• 作为产物：
  描述：

  3,5-二(溴甲基)甲苯 、 L-脯氨酸 在 potassium hydroxide 、 盐酸 作用下， 以 异丙醇 、 氯仿 、 水 为溶剂， 反应 9.0h， 生成 (2S,2'S)-1,1'-(5-methyl-1,3-phenylene)bis(methylene)dipyrrolidine-2-carboxylic acid
  参考文献：
  名称：

  Enantioselective Nucleophilic Addition of Trimethylsilylacetylene to N-Phosphinoylimines Promoted by C₂-Symmetric Proline-Derived β-Amino Alcohol

  摘要：

  Both C-2- and C-3-symmetric proline-derived beta-amine alcohol ligands were designed, synthesized, and successfully applied to the enantioselective direct addition of trimethylsilylacetylene to N-phosphinoylimines. Aromatic, heteroaromatic, and aliphatic N-(diphenylphosphinoyl) imines and several N-(diethoxyphosphoryl) imines were tested, and optically active propargylic amides in good yields (up to 92%) and excellent enantioselectivities (up to 95%) were obtained by the simple experimental procedure. The convenience, mild conditions, and easy deprotection of the phosphonamide products made the present method very attractive. Furthermore, the Michael-type addition process of C=N alkynylation was studied and proposed on the basis of React P-31 NMR investigation.

  DOI：

  10.1021/jo901492w

文献信息

• Enantioselective Nucleophilic Addition of Trimethylsilylacetylene to <i>N</i>-Phosphinoylimines Promoted by <i>C</i>₂-Symmetric Proline-Derived β-Amino Alcohol
  作者：Shaoqun Zhu、Wenjin Yan、Bin Mao、Xianxing Jiang、Rui Wang

  DOI：10.1021/jo901492w

  日期：2009.9.18

  Both C-2- and C-3-symmetric proline-derived beta-amine alcohol ligands were designed, synthesized, and successfully applied to the enantioselective direct addition of trimethylsilylacetylene to N-phosphinoylimines. Aromatic, heteroaromatic, and aliphatic N-(diphenylphosphinoyl) imines and several N-(diethoxyphosphoryl) imines were tested, and optically active propargylic amides in good yields (up to 92%) and excellent enantioselectivities (up to 95%) were obtained by the simple experimental procedure. The convenience, mild conditions, and easy deprotection of the phosphonamide products made the present method very attractive. Furthermore, the Michael-type addition process of C=N alkynylation was studied and proposed on the basis of React P-31 NMR investigation.