ethyl (R)-2-hydroxy-3-phenylpropanoate | 20918-88-1

• 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: ethyl (R)-2-hydroxy-3-phenylpropanoate
• 英文别名: ethyl (R)-phenyllactate；(R)-ethyl-2-hydroxy-3-phenylpropionate；ethyl phenyllactate；(R)-ethyl phenyllactate；(R)-ethyl 3-phenyllactate；(R)-2-hydroxy-3-phenyl-propionic acid ethyl ester；(R)-2-Hydroxy-3-phenyl-propionsaeure-aethylester；(2R)-ethyl 2-Hydroxy-3-phenylproponate；Benzenepropanoic acid, alpha-hydroxy-, ethyl ester, (alphaR)-；ethyl (2R)-2-hydroxy-3-phenylpropanoate
• CAS: 20918-88-1
• 化学式: C₁₁H₁₄O₃
• 分子量: 194.23
• InChiKey: HBOGUIFRIAXYNB-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl (R)-2-hydroxy-3-phenylpropanoate 在 咪唑 、 四丁基氟化铵 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 19.25h， 生成 (R)-1-phenylbut-3-en-2-ol
  参考文献：
  名称：

  Shimazaki, Makoto; Okazaki, Fumiaki; Nakajima, Fumihiro, Heterocycles, 1993, vol. 36, # 8, p. 1823 - 1836

  摘要：

  DOI：
• 作为产物：
  描述：

  3-苯基环氧乙烷甲酸乙酯 在 palladium on activated charcoal 氢气 作用下， 以 正己烷 为溶剂， 反应 0.75h， 生成 ethyl (R)-2-hydroxy-3-phenylpropanoate
  参考文献：
  名称：

  Sundholm, Oskari; Kanerva, Liisa T., ACH - Models in Chemistry, 1998, vol. 135, # 4, p. 625 - 640

  摘要：

  DOI：

文献信息

• [EN] MACROCYCLIC INHIBITORS OF HEPATITIS C PROTEASE<br/>[FR] INHIBITEURS MACROCYCLIQUES DE LA PROTÉASE DU VIRUS DE L'HÉPATITE C
  申请人：PHENOMIX CORP

  公开号：WO2010033466A1

  公开（公告）日：2010-03-25

  The invention provides macrocyclic compounds inhibitory to the Hepatitis C viral protease, compositions and combinations including the compounds, methods of treatment of conditions wherein inhibition of the Hepatitis C viral protease is medically indicated, and methods of treatment of a Hepatitis C viral infection in a human patient.

  本发明提供了一种抑制丙型肝炎病毒蛋白酶的大环化合物，包括该化合物的组合物、组合物、治疗方法，在医学上有抑制丙型肝炎病毒蛋白酶的指征的条件下的治疗方法，以及治疗人类患者丙型肝炎病毒感染的方法。
• Tyrosine phosphatase inhibitors
  申请人：——

  公开号：US20030144338A1

  公开（公告）日：2003-07-31

  A compound of the formula (I): 1 wherein X 1 and X 2 are the same or different and each is a bond or a spacer having 1 to 20 atom(s) in the main chain; one of R 1 and R 2 is a cycle group having substituent(s) selected from 1) an optionally substituted carboxy-C 1-6 alkoxy group and 2) an optionally substituted carboxy-C 1-6 aliphatic hydrocarbon group, wherein the cycle group optionally has additional substituent(s), and the other is an optionally substituted cycle group or a hydrogen atom; and R 3 , R 4 and R 5 are the same or different and each is a hydrogen atom or a substituent, or R 4 may link together with R 3 or R 5 to form an optionally substituted ring; provided that when R 3 is a hydrogen atom, R 4 is a hydrogen atom and R 5 is methyl, X 2 —R 2 is not 4-cyclohexylphenyl; when R 3 is 4-methoxyphenyl, R 4 is a hydrogen atom and R 5 is methyl, X 2 —R 2 is not 4-methoxyphenyl; and when R 1 or R 2 is a hydrogen atom, the adjacent X 1 or X 2 is not a C 1-7 alkylene; or a salt thereof exhibits a protein tyrosine phosphatase inhibitory action and is useful as a prophylactic or therapeutic agent for diabetes or the like.

  式（I）的化合物： 其中X1和X2相同或不同，每个都是主链中具有1至20个原子的键或间隔物； R1和R2中的一个是具有取代基的环基，所述取代基选自1）可选择地取代的羧基-C1-6烷氧基和2）可选择地取代的羧基-C1-6脂肪烃基，其中所述环基可选择地具有额外的取代基，另一个是可选择地取代的环基或氢原子；以及 R3、R4和R5相同或不同，每个是氢原子或取代基，或R4可以与R3或R5结合形成可选择地取代的环； 但是当R3是氢原子时，R4是氢原子且R5是甲基时，X2—R2不是4-环己基苯基；当R3是4-甲氧基苯基，R4是氢原子且R5是甲基时，X2—R2不是4-甲氧基苯基；当R1或R2是氢原子时，相邻的X1或X2不是C1-7烷基； 或其盐具有蛋白酪氨酸磷酸酶抑制作用，并且可用作糖尿病等疾病的预防或治疗剂。
• Substituted carbamoylmethylamino acetic acid derivatives as novel NEP inhibitors
  申请人：IWAKI Yuki

  公开号：US20110124695A1

  公开（公告）日：2011-05-26

  The present invention provides a compound of formula I: or a pharmaceutically acceptable salt thereof, wherein R 1 , R 2 , R 3 , R 4 , R 6 , A 1 , A 2 , X 1 , s and m are defined herein. The invention also relates to a method for manufacturing the compounds of the invention, and its therapeutic uses. The present invention further provides a combination of pharmacologically active agents and a pharmaceutical composition.

  本发明提供了以下式I的化合物： 或其药学上可接受的盐，其中R 1 ，R 2 ，R 3 ，R 4 ，R 6 ，A 1 ，A 2 ，X 1 ，s和m在此处定义。该发明还涉及制造该发明化合物的方法及其治疗用途。本发明还提供了药理活性剂的组合和药物组成。
• Asymmetric synthesis of α-hydroxy acids via β-Lactams
  作者：V. Srirajan、A.R.A.S. Deshmukh、V.G. Puranik、B.M. Bhawal

  DOI：10.1016/0957-4166(96)00352-7

  日期：1996.9

  A diastereoselective synthesis of β-Lactams 5a-e and 6a-e has been achieved, via a Staudinger reaction using imines derived from (1S)-(+)-camphor-10-sulfonamide, in good yields. The major diastereomers 6a-e were isolated in pure form by crystallization. The absolute configuration of the β-lactam 6b was established as 3R and 4S by X-ray analysis. The major diastereomers 6b and 6c were converted into

  β-内酰胺5a-e和6a-e的非对映选择性合成已通过Staudinger反应，使用衍生自（1 S）-（+）-樟脑10磺酰胺的亚胺以高收率实现。通过结晶分离出纯净形式的主要非对映异构体6a-e。通过X射线分析将β-内酰胺6b的绝对构型确定为3R和4S。主要的非对映异构体6b和6c转化为对映体纯的α-羟基酯衍生物7-9。
• Stereochemical control in microbial reduction. Part 31: Reduction of alkyl 2-oxo-4-arylbutyrates by baker's yeast under selected reaction conditions
  作者：Duc Hai Dao、Mutsuo Okamura、Takeshi Akasaka、Yasushi Kawai、Kouichi Hida、Atsuyoshi Ohno

  DOI：10.1016/s0957-4166(98)00277-8

  日期：1998.8

  Treatment of baker's yeast with phenacyl chloride in an aqueous–organic solvent has been proven to be an effective method of inhibiting the enzymes that afford (S)-enantiomers of α-hydroxy esters in the reduction of α-keto esters. The procedure is effective for the whole-cell system to produce the (R)-product with high chemical yield and high enantiomeric excess.

  已证明在水-有机溶剂中用苯甲酰氯处理面包酵母是抑制α-羟基酯还原中提供α-羟基酯的（S）-对映异构体的酶的有效方法。该方法对于全细胞系统生产具有高化学产率和高对映体过量的（R）产物是有效的。