Dimethyl 2-(2-methylpropylidene)butanedioate | 80459-36-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Dimethyl 2-(2-methylpropylidene)butanedioate
• 英文别名: dimethyl 2-(2-methylpropylidene)butanedioate
• CAS: 80459-36-5
• 化学式: C₁₀H₁₆O₄
• 分子量: 200.235
• InChiKey: TYKICVMVIGSBRF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Dimethyl 2-(2-methylpropylidene)butanedioate 在 sodium hydroxide 、 乙酰氯 作用下， 反应 75.0h， 生成 (E)-4-methyl-2-(2-oxo-2-phenylmethoxyethyl)pent-2-enoic acid
  参考文献：
  名称：

  MMPs inhibitors: new succinylhydroxamates with selective inhibition of MMP-2 over MMP-3

  摘要：

  Some ilomastat analogues featuring an isobutylidene group or a 2-substituted indole nucleus were synthesized to evaluate their inhibitory activities against gelatinase A and stromelysin-1. Potent MMP-2 inhibition and good selectivity for that enzyme have been observed for compounds 1a, 2 and 22. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00590-0
• 作为产物：
  描述：

  methyl 3-hydroxy-4-methyl-2-methylenepentanoate 在 palladium diacetate 、 三苯基膦 吡啶 、 4-二甲氨基吡啶 作用下， 以 苯 为溶剂， 25.0~50.0 ℃ 、2.03 MPa 条件下， 反应 15.0h， 生成 Dimethyl 2-(2-methylpropylidene)butanedioate
  参考文献：
  名称：

  Stereochemical study on the palladium(O)-catalyzed carbonylation of 3-(methoxycarbonyloxy)-2-methylenealkanoates and analogues

  摘要：

  A series of 3-(alkoxycarbonyloxy)-2-methylenealkanoate (1), a sulfonate (5), and an N,N-dimethylamide (6) were carbonylated using Pd(0) complexes as catalyst to give alkylidenesuccinate (2), and analogues in moderate to good yields. The stereoselectivity for E and Z isomers of carbonylation products was found to differ remarkably, depending on the three types of substrates which always include an electron-withdrawing group. The results are explained in terms of the plausible MM2 simulation through the model compounds.

  DOI：

  10.1016/s0040-4020(01)88755-x

文献信息

• Stereochemical study on the palladium(O)-catalyzed carbonylation of 3-(methoxycarbonyloxy)-2-methylenealkanoates and analogues
  作者：Shu-Zhong Wang、Keiji Yamamoto、Harou Yamada、Takashi Takahashi

  DOI：10.1016/s0040-4020(01)88755-x

  日期：1992.3

  A series of 3-(alkoxycarbonyloxy)-2-methylenealkanoate (1), a sulfonate (5), and an N,N-dimethylamide (6) were carbonylated using Pd(0) complexes as catalyst to give alkylidenesuccinate (2), and analogues in moderate to good yields. The stereoselectivity for E and Z isomers of carbonylation products was found to differ remarkably, depending on the three types of substrates which always include an electron-withdrawing group. The results are explained in terms of the plausible MM2 simulation through the model compounds.
• MMPs inhibitors: new succinylhydroxamates with selective inhibition of MMP-2 over MMP-3
  作者：Valérie Marcq、Catherine Mirand、Martine Decarme、Hervé Emonard、William Hornebeck

  DOI：10.1016/s0960-894x(03)00590-0

  日期：2003.9

  Some ilomastat analogues featuring an isobutylidene group or a 2-substituted indole nucleus were synthesized to evaluate their inhibitory activities against gelatinase A and stromelysin-1. Potent MMP-2 inhibition and good selectivity for that enzyme have been observed for compounds 1a, 2 and 22. (C) 2003 Elsevier Ltd. All rights reserved.