2-(2-(benzyloxy)-2-oxoethyl)-3-methylbut-2-enoic acid | 151927-79-6

• 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: 2-(2-(benzyloxy)-2-oxoethyl)-3-methylbut-2-enoic acid
• 英文别名: 4-phenylmethyl (1-methylethylidene)butanedioate；3-Methyl-2-(2-oxo-2-phenylmethoxyethyl)but-2-enoic acid
• CAS: 151927-79-6
• 化学式: C₁₄H₁₆O₄
• 分子量: 248.279
• InChiKey: HSHLCXXKHHUXKZ-UHFFFAOYSA-N

物化性质

• 熔点：
  119-120 °C
• 沸点：
  426.7±33.0 °C(predicted)
• 密度：
  1.167±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 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-(benzyloxy)-2-oxoethyl)-3-methylbut-2-enoic acid 在 platinum(IV) oxide 、 palladium on activated charcoal 水 、 氢气 、 1-羟基苯并三唑 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 126.0h， 生成 3-[[4-Oxo-4-(phenylmethoxyamino)-2-propan-2-ylbutanoyl]amino]propanoic acid
  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：

  4,4-二甲基衣康酸 在 乙酰氯 作用下， 以 氯仿 为溶剂， 反应 72.33h， 生成 2-(2-(benzyloxy)-2-oxoethyl)-3-methylbut-2-enoic acid
  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

文献信息

• Iridium-Catalyzed Enantioselective Hydrogenation of α,β-Unsaturated Carboxylic Acids with Tetrasubstituted Olefins
  作者：Song Song、Shou-Fei Zhu、Yu Li、Qi-Lin Zhou

  DOI：10.1021/ol401593a

  日期：2013.7.19

  A highly efficient asymmetric hydrogenation of α,β-unsaturated carboxylic acids with tetrasubstituted olefin catalyzed by chiral spiro iridium complexes has been developed for the preparation of chiral α-substituted carboxylic acids in excellent enantioselectivities (up to 99% ee).

  已经开发出由手性螺铱配合物催化的具有四取代烯烃的α，β-不饱和羧酸的高效不对称加氢，用于制备具有优异对映选择性（至多99％ee）的手性α-取代的羧酸。