3-苯基-2-环氧乙烷羧酸 | 5694-02-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 中文名称: 3-苯基-2-环氧乙烷羧酸
• 英文名称: 2,3-epoxy-3-phenylpropanoic acid
• 英文别名: phenyl glycidate；epoxy cinnamic acid；2,3-Epoxy-3-phenyl-propionsaeure；Phenylglycidsaeure；3-phenyl-oxiranecarboxylic acid；β-Phenylglycidsaeure；3-Phenyloxirane-2-carboxylic acid
• CAS: 5694-02-0
• 化学式: C₉H₈O₃
• mdl: MFCD03624152
• 分子量: 164.161
• InChiKey: HALONVPKHYIEQU-UHFFFAOYSA-N

物化性质

• 沸点：
  346.8±42.0 °C(Predicted)
• 密度：
  1.359±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：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2918990090

反应信息

• 作为反应物：
  描述：

  3-苯基-2-环氧乙烷羧酸 在 sodium azide 、 copper(II) nitrate trihydrate 作用下， 以 水 为溶剂， 以55%的产率得到3-azido-2-hydroxyhexanoic 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：

  2-chloro-3-hydroxy-3-phenyl-propionic acid 生成 3-苯基-2-环氧乙烷羧酸
  参考文献：
  名称：

  Smith, Zeitschrift fur Physikalische Chemie, Stoechiometrie und Verwandtschaftslehre, 1913, vol. 81, p. 346

  摘要：

  DOI：

文献信息

• [EN] NOVEL LACTAMS AND USES THEREOF<br/>[FR] NOUVELLES LACTAMES ET UTILISATIONS DE CES DERNIERES
  申请人：ASTRAZENECA AB

  公开号：WO2004031154A1

  公开（公告）日：2004-04-15

  Compounds having the formula (I) pharmaceutical compositions containing them and their methods of use for the treatment of neurological disorders related to amyloid ß protein production and neurological disorders such as Alzheimer's disease.. These compounds inhibit γ secretase and thereby inhibit the production of amyloid ß protein, thereby acting to prevent the formation of neurological deposits of amyloid protein.

  具有化学式（I）的化合物，含有它们的药物组合物以及它们用于治疗与淀粉样蛋白ß产生相关的神经系统疾病和阿尔茨海默病等神经系统疾病的方法。这些化合物抑制γ-分泌酶，从而抑制淀粉样蛋白ß的产生，从而防止神经系统中淀粉样蛋白的沉积形成。
• Catalytic oxidation of aldehydes to carboxylic acids with hydrogen peroxide as oxidant
  作者：Joong-Kwon Choi、Young-Kil Chang、Sung Yeap Hong

  DOI：10.1016/s0040-4039(00)82091-2

  日期：1988.1

  Alkyl and aryl aldehydes were catalytically oxidized to carboxylic acids in high yields with hydrogen peroxide as oxidant using benzeneseleninic acid as catalyst.

  使用过氧化氢作为氧化剂，使用苯硒酸作为催化剂，将烷基和芳基醛高产率催化氧化为羧酸。
• Exploring the Scope of an α/β-Aminomutase for the Amination of Cinnamate Epoxides to Arylserines and Arylisoserines
  作者：Prakash K. Shee、Nishanka Dilini Ratnayake、Tyler Walter、Olivia Goethe、Edith Ndubuaku Onyeozili、Kevin D. Walker

  DOI：10.1021/acscatal.9b01557

  日期：2019.8.2

  signals confirmed the diastereomeric ratios and relative stereochemistries. Application of a (2S)-threonine aldolase from E. coli further established the absolute stereochemistry of the chiral derivatives of the diastereomeric enzymatically derived products. The 2R:2S ratio for the biocatalyzed anti-isomers was highest (88:12) for 3′-NO2-phenylserine and lowest (66:34) for 4′-F-phenylserine. This showed

  生物催化工艺的发展继续朝着发现替代转化反应以合成精细化学品的方向发展。在这里，来自加拿大红豆杉的5-甲叉基-3,5-二氢-4 H-咪唑-4-酮（MIO）依赖性苯丙氨酸氨基变位酶（Tc PAM）被不可逆转地用于生物催化分子间胺转移反应，该反应转化为环取代的反式-肉桂酸酯环氧化物外消旋体为其相应的芳基丝氨酸。在12种底物中，氨基变位酶将3'-Cl-肉桂酸环氧化物开环成3'-Cl-苯基丝氨酸的速度比其4'-Cl-异构体的打开速度快140倍，而在所有测试的环氧化物中，其翻转速度都最慢。对生物催化的苯基丝氨酸类似物的手性辅助衍生物的GC / MS分析表明，Tc PAM转氨反应可对映和非对映选择性地打开环氧化物。每个产品混合物含有（2小号）+（2 - [R ）-反（赤）和（2小号）+（2 - [R ）-顺式（苏式）对与该抗-异构体占主导地位（〜90：10 dr）。在积分邻位质子信号1个酶催化phenylserines的1
• Synthesis of taxol, analogs and intermediates with variable A-nng side chains
  申请人：BRYN MAWR COLLEGE

  公开号：EP1260507A1

  公开（公告）日：2002-11-27

  An efficient protocol for the synthesis of taxol, taxol analogs, and their intermediates is described. The process includes the attachment of the taxol A-ring side chain to baccatin III and for the synthesis of taxol and taxol analogs with variable A-ring side chain structures. A rapid and highly efficient esterification of O-protected isoserine and 3-phenylisoserine acids having N-benzyoloxycarbonyl groups to the C-13 hydroxyl of 7-O-protected baccatin III is followed by a deprotection-acylation sequence to make taxol, calphalomanninne and various analogs, including photoaffinity labeling candidates.

  本文介绍了一种有效的紫杉醇、紫杉醇类似物及其中间体的合成协议。该过程包括将紫杉醇A环侧链连接到紫杉醇前体baccatin III上，以及用具有可变A环侧链结构的化合物合成紫杉醇和紫杉醇类似物。通过快速高效的酯化反应，将O保护的异丝氨酸和3-苯基异丝氨酸酸与N-苄氧羰基基团连接到7-O保护的baccatin III的C-13羟基上，然后进行去保护-酰化序列，制备紫杉醇、卡法洛曼宁和各种类似物，包括光亲和标记候选物。
• Direct epoxidation of unprotected olefinic carboxylic acids using HOF-CH3CN
  作者：Shlomo Rozen、Yifat Bareket、Sharon Dayan

  DOI：10.1016/0040-4039(95)02180-9

  日期：1996.1

  The reaction of HOF·CH3CN complex, made directly by passing fluorine through aqueous acetonitrile, with double bond containing unprotected carboxylic acids and alcohols results in fast and almost quantitative epoxidation.

  通过使氟通过乙腈水溶液直接与含有未保护的羧酸和醇的双键直接形成的HOF·CH 3 CN络合物的反应导致快速且几乎定量的环氧化。