(2S,αS)-1-(α-(1,1,3,3-tetramethylbutyl)-carbamoyl-α-phenylmethyl)-pyrrolidine-2-carboxylic acid methyl ester | 1397679-95-6

• 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,αS)-1-(α-(1,1,3,3-tetramethylbutyl)-carbamoyl-α-phenylmethyl)-pyrrolidine-2-carboxylic acid methyl ester
• CAS: 1397679-95-6
• 化学式: C₂₂H₃₄N₂O₃
• 分子量: 374.524
• InChiKey: XQTJUZTZFWUQJC-ROUUACIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  27.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  58.64
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2S,αS)-1-(α-(1,1,3,3-tetramethylbutyl)-carbamoyl-α-phenylmethyl)-pyrrolidine-2-carboxylic acid methyl ester 在 boron trifluoride diacetate 作用下， 以81%的产率得到methyl (2S)-1-[(S)-2-amino-2-oxo-1-phenylethyl]pyrrolidine-2-carboxylate
  参考文献：
  名称：

  Synthesis of bicyclic 2,6-diketopiperazines via a three-step sequence involving an Ugi five-center, four-component reaction

  摘要：

  A three-step sequence involving an Ugi five-center, four-component reaction (U-5C-4CR), amide N-detertbutylation and cyclocondensation has been developed for easy access to diverse bicyclic 2,6-diketopiperazine (2,6-DKP) derivatives. In the key step, aromatic aldehydes were successfully coupled with cyclic alpha-amino acids and isocyanides in the course of U-5C-4CR. Boron trifluoride-acetic acid complex was developed as a new N-detertbutylating agent effective at rt. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.07.064
• 作为产物：
  描述：

  甲醇 、 1,1,3,3-四甲基丁基异腈 、 苯甲醛 、 L-脯氨酸 在 iron(III) chloride 作用下， 反应 24.0h， 以38%的产率得到(2S,αS)-1-(α-(1,1,3,3-tetramethylbutyl)-carbamoyl-α-phenylmethyl)-pyrrolidine-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis of bicyclic 2,6-diketopiperazines via a three-step sequence involving an Ugi five-center, four-component reaction

  摘要：

  A three-step sequence involving an Ugi five-center, four-component reaction (U-5C-4CR), amide N-detertbutylation and cyclocondensation has been developed for easy access to diverse bicyclic 2,6-diketopiperazine (2,6-DKP) derivatives. In the key step, aromatic aldehydes were successfully coupled with cyclic alpha-amino acids and isocyanides in the course of U-5C-4CR. Boron trifluoride-acetic acid complex was developed as a new N-detertbutylating agent effective at rt. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.07.064