3-Ethyloxirane-2-carboxylic acid | 5699-62-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: 3-Ethyloxirane-2-carboxylic acid
• CAS: 5699-62-7
• 化学式: C₅H₈O₃
• mdl: MFCD19230020
• 分子量: 116.117
• InChiKey: JEFQGTDZXWGWMD-UHFFFAOYSA-N

物化性质

• 沸点：
  230.1±33.0 °C(Predicted)
• 密度：
  1.233±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-Ethyloxirane-2-carboxylic acid 在 sodium azide 、 copper(II) nitrate trihydrate 、 1-羟基苯并三唑 、 戴斯-马丁氧化剂 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 N,N-二异丙基乙胺 、 tin(ll) chloride 作用下， 以 N-甲基吡咯烷酮 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 (4S,7S,10S)-4-((S)-sec-butyl)-13-ethyl-7-((R)-1-hydroxyethyl)-2,5,8,11,14,15-hexaoxo-3,6,9,12,16-pentaazanonadecan-19-oic acid
  参考文献：
  名称：

  Substrate derived peptidic α-ketoamides as inhibitors of the malarial protease PfSUB1

  摘要：

  Peptidic alpha-ketoamides have been developed as inhibitors of the malarial protease PfSUB1. The design of inhibitors was based on the best known endogenous PfSUB1 substrate sequence, leading to compounds with low micromolar to submicromolar inhibitory activity. SAR studies were performed indicating the requirement of an aspartate mimicking the P-1' substituent and optimal P-1-P-4 length of the non-prime part. The importance of each of the P-1-P-4 amino acid side chains was investigated, revealing crucial interactions and size limitations. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.07.086
• 作为产物：
  描述：

  丙醛 、 氯乙酸 在 lithium diisopropyl amide 作用下， 生成 3-Ethyloxirane-2-carboxylic acid
  参考文献：
  名称：

  Dianions derived from .alpha.-halo acids. The Darzens condensation revisited

  摘要：

  DOI：

  10.1021/jo00346a013

文献信息

• Dianions derived from .alpha.-halo acids. The Darzens condensation revisited
  作者：Carl R. Johnson、Thomas R. Bade

  DOI：10.1021/jo00346a013

  日期：1982.3
• Substrate derived peptidic α-ketoamides as inhibitors of the malarial protease PfSUB1
  作者：Samir S. Kher、Maria Penzo、Simone Fulle、Paul W. Finn、Michael J. Blackman、Aigars Jirgensons

  DOI：10.1016/j.bmcl.2014.07.086

  日期：2014.9

  Peptidic alpha-ketoamides have been developed as inhibitors of the malarial protease PfSUB1. The design of inhibitors was based on the best known endogenous PfSUB1 substrate sequence, leading to compounds with low micromolar to submicromolar inhibitory activity. SAR studies were performed indicating the requirement of an aspartate mimicking the P-1' substituent and optimal P-1-P-4 length of the non-prime part. The importance of each of the P-1-P-4 amino acid side chains was investigated, revealing crucial interactions and size limitations. (C) 2014 Elsevier Ltd. All rights reserved.