(S)-methyl 2-(((((1R,2S)-2-allylcyclopentyl)oxy)carbonyl)amino)-2-cyclopentylacetate | 1414868-52-2

• 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)-methyl 2-(((((1R,2S)-2-allylcyclopentyl)oxy)carbonyl)amino)-2-cyclopentylacetate
• 英文别名: methyl (2S)-2-cyclopentyl-2-[[(1R,2S)-2-prop-2-enylcyclopentyl]oxycarbonylamino]acetate
• CAS: 1414868-52-2
• 化学式: C₁₇H₂₇NO₄
• 分子量: 309.406
• InChiKey: LYNSBHXGKXLHPC-YUELXQCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-methyl 2-(((((1R,2S)-2-allylcyclopentyl)oxy)carbonyl)amino)-2-cyclopentylacetate 在 lithium hydroxide monohydrate 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 四氢呋喃 、 甲醇 、 水 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 methyl (6R,8S,11S,14aR,17aS,19E)-11-cyclopentyl-3-ethoxy-23-methoxy-10,13-dioxo-7,8,10,11,12,13,14a,15,16,17,17a,18-dodecahydro-6H-1,21-(ethanediylidene)-6,9-methanocyclopenta[r]pyrido[4,3-k][1,10,3,6]dioxadiazacyclononadecine-8-carboxylate
  参考文献：
  名称：

  Development of macrocyclic inhibitors of HCV NS3/4A protease with cyclic constrained P2–P4 linkers

  摘要：

  A series of macrocyclic compounds containing a cyclic constraint in the P2-P4 linker region have been discovered and shown to exhibit excellent HCV NS3/4a genotype 3a and genotype 1b R155 K, A156T, A156 V, and D168 V mutant activity while maintaining high rat liver exposure. The effect of the constraint is most dramatic against gt 1b A156 mutants where similar to 20-fold improvements in potency are achieved by introduction of a variety of ring systems into the P2-P4 linker. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.09.061
• 作为产物：
  描述：

  (1R,2S)-2-(2-propenyl)cyclopentyl acetate 在 4-二甲氨基吡啶 、 potassium carbonate 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 7.0h， 生成 (S)-methyl 2-(((((1R,2S)-2-allylcyclopentyl)oxy)carbonyl)amino)-2-cyclopentylacetate
  参考文献：
  名称：

  Development of macrocyclic inhibitors of HCV NS3/4A protease with cyclic constrained P2–P4 linkers

  摘要：

  A series of macrocyclic compounds containing a cyclic constraint in the P2-P4 linker region have been discovered and shown to exhibit excellent HCV NS3/4a genotype 3a and genotype 1b R155 K, A156T, A156 V, and D168 V mutant activity while maintaining high rat liver exposure. The effect of the constraint is most dramatic against gt 1b A156 mutants where similar to 20-fold improvements in potency are achieved by introduction of a variety of ring systems into the P2-P4 linker. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.09.061