(R, S)-ethyl 3-(2-hydroxyphenoxy)propanoate | 79228-69-6

• 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: (R, S)-ethyl 3-(2-hydroxyphenoxy)propanoate
• 英文别名: ethyl 2-(m-hydroxyphenoxy)propionate；ethyl 2-(3-hydroxyphenoxy)propionate；Ethyl 2-(3-hydroxyphenoxy)propanoate
• CAS: 79228-69-6
• 化学式: C₁₁H₁₄O₄
• 分子量: 210.23
• InChiKey: LUDNSXYVHXHLMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 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：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R, S)-ethyl 3-(2-hydroxyphenoxy)propanoate 在 4-二甲氨基吡啶 、 氢氧化钾 、 三氟化硼乙醚 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醚 、 乙醇 、 二氯甲烷 为溶剂， 生成 3-o-methoxyphenoxycarbonyl-(α-methyl)methenyloxyphenyl-dihydroartemisinin ether
  参考文献：
  名称：

  新青蒿素衍生物的合成和免疫抑制活性。1. [12(β或α)-二氢青蒿氧]苯(氧)基脂肪酸和酯。

  摘要：

  合成了一系列新的双氢青蒿素衍生物并评估了它们的免疫抑制活性，以寻找具有高效低毒的潜在免疫抑制剂。测定了这些化合物对淋巴细胞的细胞毒性、对刀豆蛋白 A (ConA) 诱导的 T 细胞增殖和脂多糖 (LPS) 诱导的 B 细胞增殖的抑制活性。其中，与青蒿素、青蒿琥酯和蒿甲醚相比，11b、13b、14d、15b、16和17在体外对丝裂原诱导的T细胞和B细胞增殖具有显着的细胞毒性和抑制活性。更重要的是，与环孢菌素 A (CsA) 相比，化合物 11b 的细胞毒性降低了 100 多倍，对 ConA 诱导的 T 细胞增殖的抑制活性 (SI = 848) 与 CsA (SI = 963) 相当，抑制作用 (SI = 28473) 与体外 CsA (SI = 7) 相比，LPS 诱导的 B 细胞增殖。体内实验结果表明，化合物16可分别抑制2,4-二硝基氟苯（DNFB）诱导的迟发型超敏反应（DTH）和绵羊红

  DOI：

  10.1021/jm048979c
• 作为产物：
  描述：

  间苯二酚 生成 (R, S)-ethyl 3-(2-hydroxyphenoxy)propanoate
  参考文献：
  名称：

  SASUGA, MASASI;KIMOTO, RYUKAJ;KOIKEH, VATARO;YASAVA, TIXIRO

  摘要：

  DOI：

文献信息

• [EN] A PROCESS FOR THE PREPARATION OF TRIAZINE INTERMEDIATES AND A PROCESS FOR THE PREPARATION OF UV ABSORBERS THEREOF<br/>[FR] PROCÉDÉ DE PRÉPARATION D'INTERMÉDIAIRES DE TRIAZINE ET PROCÉDÉ DE PRÉPARATION D'ABSORBEURS UV ASSOCIÉS
  申请人：BASF SE

  公开号：WO2020144093A1

  公开（公告）日：2020-07-16

  The presently claimed invention relates to a novel, highly efficient and general process for the preparation of the triazine intermediates and their use in the preparation of UV absorbers.

  目前所声称的发明涉及一种新颖、高效和通用的三嗪中间体制备过程及其在制备紫外线吸收剂中的应用。
• ARTEMISINE (QINGHAOSU) DERIVATIVES, THEIR PREPARATION METHODS AND THEIR USE, AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME
  申请人：Shanghai Institute of Materia Medica, Chinese Academy of Sciences

  公开号：EP1845099B1

  公开（公告）日：2012-10-24
• Resolution of (R, S)-ethyl-2-(4-hydroxyphenoxy) propanoate using lyophilized mycelium of Aspergillus oryzae WZ007
  作者：Jian-Yong Zheng、Jia-Yu Wu、Yin-Jun Zhang、Zhao Wang

  DOI：10.1016/j.molcatb.2013.07.016

  日期：2013.12

  The mycelium of Aspergillus oryzae WZ007 was successfully developed to kinetic resolution of (R, S)-ethyl-2-(4-hydroxyphenoxy) propanoate ((R, S)-EHPP) for production of (R)-ethyl-2-(4-hydroxyphenoxy) propanoate ((R)-EHPP). The key biocatalytic process parameters (pH, temperature, rotation speed and substrate concentration) were optimized. Under the optimum conditions, the optical purity of (R)-EHPP was improved up to >99% when the conversion was above 49%. A. oryzae WZ007 whole-cell lipase exhibited high reaction capacity, enantioselectivity and good reusability. The tolerable substrate concentration was 0.5 mol/L, and dry mycelium of A. oryzae WZ007 maintains over 80% of its initial activity after eight repeating cycles. Therefore the enzymatic preparation of (R)-EHPP route was suitable for industrial application. (C) 2013 Elsevier B.V. All rights reserved.
• A PROCESS FOR THE PREPARATION OF TRIAZINE INTERMEDIATES AND A PROCESS FOR THE PREPARATION OF UV ABSORBERS THEREOF
  申请人：BASF SE

  公开号：EP3908633A1

  公开（公告）日：2021-11-17
• Artemisinin (Qinghaosu) Derivatives, Their Preparation Methods And Their Use, And Pharmaceutical Compositions Containing The Same
  申请人：Li Ying

  公开号：US20080139642A1

  公开（公告）日：2008-06-12

  The invention provides a type of artemisinin derivatives having following structure I, its preparation method and use, as well as a pharmaceutical composition containing such artemisinin derivatives and its use. The artemisinin derivatives of the present invention and their pharmaceutical composition containing the artemisinin derivatives. have immunosuppressive activities and can be used more safely. The composition which comprises the artemisinin derivatives can be formulated into long-term dosage forms such as tablet, pellet and the like, and have wider productive and use value.