1-tert-butyl 2-methyl (2S,4R)-4-(((4-(trifluoromethyl)phenyl)sulfonyl)amino)-1,2-pyrrolidinedicarboxylate | 121148-20-7

• 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: 1-tert-butyl 2-methyl (2S,4R)-4-(((4-(trifluoromethyl)phenyl)sulfonyl)amino)-1,2-pyrrolidinedicarboxylate
• 英文别名: (2S,4R)-1-t-Butoxycarbonyl-2-methoxycarbonyl-4(4-trifluoromethylphenylsulfonylamino)pyrrolidine；1-O-tert-butyl 2-O-methyl (2S,4R)-4-[[4-(trifluoromethyl)phenyl]sulfonylamino]pyrrolidine-1,2-dicarboxylate
• CAS: 121148-20-7
• 化学式: C₁₈H₂₃F₃N₂O₆S
• 分子量: 452.452
• InChiKey: QOMAELWAJGKKRE-OCCSQVGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1-tert-butyl 2-methyl (2S,4R)-4-(((4-(trifluoromethyl)phenyl)sulfonyl)amino)-1,2-pyrrolidinedicarboxylate 在 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以92.8%的产率得到tert-butyl (2S,4R)-2-formyl-4-(((4-(trifluoromethyl)phenyl)sulfonyl)amino)pyrrolidine-1-carboxylate
  参考文献：
  名称：

  Synthesis and Biological Activity of 1-Phenylsulfonyl-4-Phenylsulfonylaminopyrrolidine Derivatives as Thromboxane A 2 Receptor Antagonists

  摘要：

  The synthesis and biological activity of novel 1-phenylsulfonyl-4- phenylsulfonylaminopyrrolidine analogues are described. All compounds were produced through modification of the substituent formally corresponding to the 1,3-dioxane ring system and the omega-octenol side chain of thromboxane A(2) (TXA(2)), in reference to the structure of Daltroban. Several compounds were found to be potent TXA(2) receptor antagonists. Compound 51a was the most effective inhibitor of 9.11-epoxymethano PGH(2) (U-46619)-induced rat aortic strip contraction (IC50 = 0.48 nM). (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00397-2
• 作为产物：
  描述：

  L-羟基脯氨酸 在 palladium on activated charcoal 氯化亚砜 、 sodium azide 、 氢气 、 potassium carbonate 、 三乙胺 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 90.0 ℃ 、303.98 kPa 条件下， 反应 26.0h， 生成 1-tert-butyl 2-methyl (2S,4R)-4-(((4-(trifluoromethyl)phenyl)sulfonyl)amino)-1,2-pyrrolidinedicarboxylate
  参考文献：
  名称：

  Synthesis and Biological Activity of 1-Phenylsulfonyl-4-Phenylsulfonylaminopyrrolidine Derivatives as Thromboxane A 2 Receptor Antagonists

  摘要：

  The synthesis and biological activity of novel 1-phenylsulfonyl-4- phenylsulfonylaminopyrrolidine analogues are described. All compounds were produced through modification of the substituent formally corresponding to the 1,3-dioxane ring system and the omega-octenol side chain of thromboxane A(2) (TXA(2)), in reference to the structure of Daltroban. Several compounds were found to be potent TXA(2) receptor antagonists. Compound 51a was the most effective inhibitor of 9.11-epoxymethano PGH(2) (U-46619)-induced rat aortic strip contraction (IC50 = 0.48 nM). (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00397-2

文献信息

• Pyrrolidine derivatives
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：EP0289911B1

  公开（公告）日：1993-06-16
• US4916152A
  申请人：——

  公开号：US4916152A

  公开（公告）日：1990-04-10