3-(methoxycarbonyl)-4-methylpent-3-enoic acid | 130165-83-2

• 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: 3-(methoxycarbonyl)-4-methylpent-3-enoic acid
• 英文别名: methyl 2-isopropylidenesuccinate；2-Isopropylidenesuccinic acid 1-methyl ester；3-methoxycarbonyl-4-methylpent-3-enoic acid
• CAS: 130165-83-2
• 化学式: C₈H₁₂O₄
• 分子量: 172.181
• InChiKey: NTEUHFNDKXZOPV-UHFFFAOYSA-N

物化性质

• 熔点：
  58 °C
• 沸点：
  295.2±23.0 °C(Predicted)
• 密度：
  1.133±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  3-(methoxycarbonyl)-4-methylpent-3-enoic acid 在 sodium hydroxide 、 乙酰氯 作用下， 以 水 为溶剂， 反应 12.33h， 生成 dihydro-3-(methylethylidene)-2,5-furandione
  参考文献：
  名称：

  Hydroxamic Acids as Potent Inhibitors of Endothelin-Converting Enzyme from Human Bronchiolar Smooth Muscle

  摘要：

  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.

  DOI：

  10.1021/jm00012a011
• 作为产物：
  描述：

  Isopropylidenbernsteinsaeure-dimethylester 在 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 7.0h， 以80%的产率得到3-(methoxycarbonyl)-4-methylpent-3-enoic 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

• Asymmetric hydrogenation
  申请人：Chirotech Technology, Ltd.

  公开号：US06414187B1

  公开（公告）日：2002-07-02

  The present invention pertains to a process for the preparation of an enantiomerically enriched chiral carboxylic acid derivative having the partial formula: C—C—C—COOX wherein X is a cation, comprising formation of a dehydro precursor salt having the partial formula: C═C—C—COOX by reaction of the corresponding precursor acid with an at least substantially stoichiometric amount of base, and asymmetric hydrogenation of the salt in the presence of a transition metal complex of a chiral phosphine ligand.

  本发明涉及一种制备对映富集的手性羧酸衍生物的过程，其部分式为：C—C—C—COOX，其中X是阳离子，包括通过将相应的前体酸与至少近似化学计量的碱反应形成具有部分式的脱氢前体盐：C═C—C—COOX，以及在手性膦配体的过渡金属配合物存在下对盐进行不对称氢化。
• Homogeneous asymmetric hydrogenation using phosphine ligands of transition metals
  申请人：Chirotech Technology, Inc.

  公开号：US06207853B1

  公开（公告）日：2001-03-27

  A process for the preparation of an enantiomerically enriched 2-substituted succinic acid derivative of formula 2, which comprises asymmetric hydrogenation of the dehydro precursor of formula 7 or 8, or a mixture thereof wherein R1 and R2 are independently H, a salt-forming cation, or an organic group of up to 30 C atoms, and R3 and R4 are independently H or an organic group of up to 30 C atoms, provided that R3 and R4 are not both H, in the presence of a transition metal complex of a chiral phosphine ligand having the partial formula 10 wherein n is 0 to 6 and R represents at least one non-hydrogen organic group of up to 30 C atoms.

  一种制备手性富集的2-取代琥珀酸衍生物的方法，其包括在具有手性膦配体的过渡金属配合物的存在下，对公式7或8的脱氢前体或其混合物进行不对称氢化反应，其中R1和R2独立地为H、盐形成阳离子或最多30个C原子的有机基团，而R3和R4独立地为H或最多30个C原子的有机基团，但要求R3和R4不能同时为H。其中手性膦配体的部分式为10，其中n为0至6，R表示至少一个最多30个C原子的非氢有机基团。
• McCabe, Richard W.; Parry, David E.; Saberi, Stephen P., Journal of the Chemical Society. Perkin transactions I, 1993, # 9, p. 1023 - 1030
  作者：McCabe, Richard W.、Parry, David E.、Saberi, Stephen P.

  DOI：——

  日期：——
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• Banerjee, Shubhra; Tayde, Ravibabu A; Sharma, Bhagyashree D, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2009, vol. 48, # 6, p. 882 - 885
  作者：Banerjee, Shubhra、Tayde, Ravibabu A、Sharma, Bhagyashree D

  DOI：——

  日期：——