(2S,3R)-2-Cyclopentyl-3-(2-methyl-allyl)-succinic acid 1-benzyl ester | 216578-59-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,3R)-2-Cyclopentyl-3-(2-methyl-allyl)-succinic acid 1-benzyl ester
• CAS: 216578-59-5
• 化学式: C₂₀H₂₆O₄
• 分子量: 330.424
• InChiKey: HOMUKQKKVBRLSL-MSOLQXFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  24.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  63.6
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2S,3R)-2-Cyclopentyl-3-(2-methyl-allyl)-succinic acid 1-benzyl ester 在 palladium on activated charcoal 氢气 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 2.0h， 生成 2S-Cyclopentyl-3R-[2,2-dimethyl-1S-(methylcarbamoyl)propylcarbamoyl]-5-methyl-hexanoic acid
  参考文献：
  名称：

  The synthesis of novel matrix metalloproteinase inhibitors employing the Ireland-Claisen rearrangement

  摘要：

  Matrix metalloproteinase inhibitors of general formula (1) were synthesised by a route involving an Ireland-Claisen rearrangement which enables systematic modification of the substituent alpha to the hydroxamic acid. An analogue (12c) possessing an alpha-cyclopentyl group is a potent broad spectrum inhibitor that displays high and sustained blood levels following oral dosing in both the rat and marmoset ex-vivo bioassays. This compound and analogues are also potent inhibitors of TNF alpha release. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00218-2
• 作为产物：
  描述：

  (R)-2-Cyclopentyl-succinic acid 1-benzyl ester 4-(2-methyl-allyl) ester 在 三乙基氯硅烷 、 lithium diisopropyl amide 作用下， 生成 (2S,3R)-2-Cyclopentyl-3-(2-methyl-allyl)-succinic acid 1-benzyl ester
  参考文献：
  名称：

  The synthesis of novel matrix metalloproteinase inhibitors employing the Ireland-Claisen rearrangement

  摘要：

  Matrix metalloproteinase inhibitors of general formula (1) were synthesised by a route involving an Ireland-Claisen rearrangement which enables systematic modification of the substituent alpha to the hydroxamic acid. An analogue (12c) possessing an alpha-cyclopentyl group is a potent broad spectrum inhibitor that displays high and sustained blood levels following oral dosing in both the rat and marmoset ex-vivo bioassays. This compound and analogues are also potent inhibitors of TNF alpha release. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00218-2