(2S, 4R)-1-N-Dodecyl-4-hydroxypyrrolidine-2-carboxylic acid, methyl ester | 221915-38-4

• 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, 4R)-1-N-Dodecyl-4-hydroxypyrrolidine-2-carboxylic acid, methyl ester
• 英文别名: methyl (2S,4R)-1-dodecyl-4-hydroxypyrrolidine-2-carboxylate
• CAS: 221915-38-4
• 化学式: C₁₈H₃₅NO₃
• 分子量: 313.481
• InChiKey: NIFLXVNVERYMON-SJORKVTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  22
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S, 4R)-1-N-Dodecyl-4-hydroxypyrrolidine-2-carboxylic acid, methyl ester 在 sodium hydroxide 、 水 作用下， 以72%的产率得到sodium N-dodecyl-4-hydroxyprolinate
  参考文献：
  名称：

  Towards novel efficient monomeric surfactants based on serine, tyrosine and 4-hydroxyproline: synthesis and micellization properties

  摘要：

  The synthesis of some novel monomeric serine- and tyrosine-based cationic and 4-hydroxyproline-based anionic surfactants, having a long lipophilic alkyl chain directly attached to the nitrogen atom of the amino acid, is described. The most efficient synthetic methodologies were established: reductive amination of the corresponding 'fatty' aldehydes, followed by methylation and deprotection (serine and tyrosine) to obtain the cationic surfactants; or reductive amination followed by saponification (4-hydroxyproline) to obtain the anionic ones. All the compounds were obtained in good to excellent yields. An assessment of their micellization properties and surface activity by tensiometry showed fairly good performance levels. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.03.043
• 作为产物：
  描述：

  十二醛 、 反式-4-羟基-L-脯氨酸甲酯盐酸盐 在 三乙胺 、 三乙酰氧基硼氢化钠 作用下， 以 1,2-二氯乙烷 为溶剂， 以85%的产率得到(2S, 4R)-1-N-Dodecyl-4-hydroxypyrrolidine-2-carboxylic acid, methyl ester
  参考文献：
  名称：

  Towards novel efficient monomeric surfactants based on serine, tyrosine and 4-hydroxyproline: synthesis and micellization properties

  摘要：

  The synthesis of some novel monomeric serine- and tyrosine-based cationic and 4-hydroxyproline-based anionic surfactants, having a long lipophilic alkyl chain directly attached to the nitrogen atom of the amino acid, is described. The most efficient synthetic methodologies were established: reductive amination of the corresponding 'fatty' aldehydes, followed by methylation and deprotection (serine and tyrosine) to obtain the cationic surfactants; or reductive amination followed by saponification (4-hydroxyproline) to obtain the anionic ones. All the compounds were obtained in good to excellent yields. An assessment of their micellization properties and surface activity by tensiometry showed fairly good performance levels. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.03.043

文献信息

• Trifluoromethyl ketone analogs as selective cPLA2 inhibitors
  申请人：Bristol-Myers Squibb Company

  公开号：US06255496B1

  公开（公告）日：2001-07-03

  Selective inhibitors of the cPLA2 enzymes are provided which are of use in controlling a wide variety of inflammatory diseases. The inhibitors of the present invention have the general formula

  提供了选择性抑制cPLA2酶的药物，可用于控制各种炎症性疾病。本发明的抑制剂具有一般公式。