2-(2-methoxy-2-oxoethyl)-3-methylbutanoic acid | 163847-93-6

• 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: 2-(2-methoxy-2-oxoethyl)-3-methylbutanoic acid
• 英文别名: 4-methyl 2-(1-metylethyl)butanedioate；(+/-)-isopropyl-succinic acid-4-methyl ester；(+/-)-Isopropyl-bernsteinsaeure-4-methylester；4-Methoxy-4-oxo-2-propan-2-ylbutanoic acid
• CAS: 163847-93-6
• 化学式: C₈H₁₄O₄
• 分子量: 174.197
• InChiKey: XUIKIMSNOFEYMT-UHFFFAOYSA-N

物化性质

• 沸点：
  272.4±23.0 °C(Predicted)
• 密度：
  1.092±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-methoxy-2-oxoethyl)-3-methylbutanoic acid 在 氯化亚砜 作用下， 生成 (+/-)-isopropyl-succinic acid-4-methyl ester-1-chloride
  参考文献：
  名称：

  Sutter; Schlittler, Helvetica Chimica Acta, 1947, vol. 30, p. 411

  摘要：

  DOI：
• 作为产物：
  描述：

  4,4-二甲基衣康酸 在 palladium on activated charcoal Amberlyst 15 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 20.0 ℃ 、303.98 kPa 条件下， 反应 20.0h， 生成 2-(2-methoxy-2-oxoethyl)-3-methylbutanoic acid
  参考文献：
  名称：

  将硝基烷烃加成到马来酸二甲酯中。2-烷基琥珀酸的两个单酯的区域选择性形成

  摘要：

  通过将硝基烷烃共轭加成到马来酸二甲酯中而获得的（E）-2-亚烷基琥珀酸的二酯可以在反应性更高的羧基上选择性地单水解成相应的半酯。可选择地，全部水解为二酸允许链烷羧基的随后的选择性甲基酯化，以给出其他区域异构的半酯。可以通过不饱和衍生物的催化加氢最终获得2-烷基琥珀酸单酯。

  DOI：

  10.1016/s0040-4020(03)01175-x

文献信息

• Hydroxamic Acids as Potent Inhibitors of Endothelin-Converting Enzyme from Human Bronchiolar Smooth Muscle
  作者：Ron Bihovsky、Barry L. Levinson、Rivka C. Loewi、Paul W. Erhardt、Mark A. Polokoff

  DOI：10.1021/jm00012a011

  日期：1995.6

  Hydroxamic acids 6a-h, derived from malonyl amino acids, and 25a-d, derived from succinyl amino acids, were synthesized as inhibitors of human bronchiolar smooth muscle endothelin-converting enzyme (HBSM ECE). Several unexpected side reactions were discovered, particularly in the synthesis of hydroxamates derived from succinates. In vitro evaluation against human bronchiolar ECE revealed that in all cases hydroxamates derived from malonate were more potent than hydroxamates derived from succinate. Isopropyl and isobutyl P-1' side chains were suitable; omission of the P-1' Side chain seriously diminished potency. In the P-2' position, several amino acids gave potent malonate-derived hydroxamate inhibitors (6b,d-h, IC50 = 0.2-6.8 nM), and beta-Ala provided an extremely potent inhibitor (6c, IC50 = 0.01 nM). C-terminus carboxylates are much more potent ECE inhibitors than the corresponding amides. Most of the hydroxamates were also potent inhibitors of thermolysin and neutral endopeptidase (NEP); however, the P-2' beta-Ala derivative 6c uniquely inhibited HBSM ECE much more potently than NEP.
• Conjugate addition of nitroalkanes to dimethyl maleate. Regioselective formation of both monoesters of 2-alkylsuccinic acids
  作者：Roberto Ballini、Giovanna Bosica、Alessandro Palmieri、Marino Petrini、Claudio Pierantozzi

  DOI：10.1016/s0040-4020(03)01175-x

  日期：2003.9

  Diesters of (E)-2-alkylidenesuccinic acids obtained by conjugate addition of nitroalkanes to dimethyl maleate can be selectively monohydrolyzed at the more reactive carboxyl group to the corresponding half-ester. Alternatively, total hydrolysis to the diacid allows a subsequent selective methyl esterification of the alkanoic carboxyl group to give the other regioisomeric half-ester. 2-Alkylsuccinic

  通过将硝基烷烃共轭加成到马来酸二甲酯中而获得的（E）-2-亚烷基琥珀酸的二酯可以在反应性更高的羧基上选择性地单水解成相应的半酯。可选择地，全部水解为二酸允许链烷羧基的随后的选择性甲基酯化，以给出其他区域异构的半酯。可以通过不饱和衍生物的催化加氢最终获得2-烷基琥珀酸单酯。
• Sutter; Schlittler, Helvetica Chimica Acta, 1947, vol. 30, p. 411
  作者：Sutter、Schlittler

  DOI：——

  日期：——