ethyl 3-hydroxy-3-(4-chlorophenyl)propanoate | 70200-14-5

• 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: ethyl 3-hydroxy-3-(4-chlorophenyl)propanoate
• 英文别名: ethyl 3-(4-chlorophenyl)-3-hydroxypropanoate；(-)-ethyl 3-(4-chlorophenyl)-3-hydroxypropionate
• CAS: 70200-14-5
• 化学式: C₁₁H₁₃ClO₃
• 分子量: 228.675
• InChiKey: XZODIRIEWWPAQC-UHFFFAOYSA-N

物化性质

• 沸点：
  347.8±27.0 °C(Predicted)
• 密度：
  1.233±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 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：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 3-hydroxy-3-(4-chlorophenyl)propanoate 在 Ru(II)-(S)-(-)-BINAP sodium tetrahydroborate 、 氢气 、 重铬酸 、 nickel dichloride 作用下， 以 吡啶 、 甲醇 、 乙醚 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， -20.0~100.0 ℃ 、5.52 MPa 条件下， 反应 203.5h， 生成 R(+)-巴氯芬盐酸盐
  参考文献：
  名称：

  通过Ru（II）-BINAP催化的不对称加氢合成（R）-（-）-baclofen的对映选择性

  摘要：

  已经描述了一种短而有效的对映选择性合成（R）-（-）-baclofen（一种选择性的GABA B激动剂）的方法，其总收率为ee的26％和90％。Ru（II）–（S）-BINAP催化CC和CO基团的不对称氢化反应是将立体异构中心引入分子的关键步骤。

  DOI：

  10.1016/s0957-4166(03)00024-7
• 作为产物：
  描述：

  对氯苯乙酮 在 sodium tetrahydroborate 、 sodium hydride 作用下， 以 甲苯 、 mineral oil 为溶剂， 反应 21.0h， 生成 ethyl 3-hydroxy-3-(4-chlorophenyl)propanoate
  参考文献：
  名称：

  Studies on the chemoenzymatic synthesis of (R)- and (S)-methyl 3-aryl-3-hydroxypropionates: the influence of toluene-pretreatment of lipase preparations on enantioselective transesterifications

  摘要：

  Two series (para- and meta-substituted) of racemic methyl esters of 3-aryl-3-hydroxypropionic acid were prepared after which the enantiomers were separated by an enzyme-catalyzed transesterification. Several lipases were investigated as the catalyst. The influence of the enzyme pretreatment, as well as substrate concentration, reaction temperature, stirring manner, and substrate conversion on the stereochemical outcome of the biotransformation process were investigated in detail. The best results were achieved by using solvent-pretreated lipase from Pseudomonas fluorescens or Burkholderia cepacia suspended in toluene, and vinyl acetate as the acetyl group donor. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.06.004

文献信息

• Diamine derivatives
  申请人：Ohta Toshiharu

  公开号：US20050020645A1

  公开（公告）日：2005-01-27

  A compound represented by the general formula (1): Q 1 -Q 2 -T 0 -N(R 1 )-Q 3 -N(R 2 )-T 1 -Q 4 (1) wherein R 1 and R 2 are hydrogen atoms or the like; Q 1 is a saturated or unsaturated, 5- or 6-membered cyclic hydrocarbon group which may be substituted, or the like; Q 2 is a single bond or the like; Q 3 is a group in which Q 5 is an alkylene group having 1 to 8 carbon atoms, or the like; and T 0 and T 1 are carbonyl groups or the like; a salt thereof, a solvate thereof, or an N-oxide thereof. The compound is useful as an agent for preventing and/or treating cerebral infarction, cerebral embolism, myocardial infarction, angina pectoris, pulmonary infarction, pulmonary embolism, Buerger's disease, deep venous thrombosis, disseminated intravascular coagulation syndrome, thrombus formation after valve or joint replacement, thrombus formation and reocclusion after angioplasty, systemic inflammatory response syndrome (SIRS), multiple organ dysfunction syndrome (MODS), thrombus formation during extracorporeal circulation, or blood clotting upon blood drawing.

  通用式（1）表示的化合物： Q1-Q2-T0-N(R1)-Q3-N(R2)-T1-Q4（1） 其中R1和R2是氢原子或类似物；Q1是饱和或不饱和的、5-或6-成员环烃基，可以被取代，或类似物；Q2是单键或类似物；Q3是一个基团，其中Q5是具有1至8个碳原子的烷基基团，或类似物；T0和T1是羰基团或类似物；其盐、溶剂合物或N-氧化物。 该化合物可用作预防和/或治疗脑梗死、脑栓塞、心肌梗死、心绞痛、肺梗死、肺栓塞、布尔格病、深静脉血栓形成、弥散性血管内凝血综合征、瓣膜或关节置换后的血栓形成、血管成形术后的血栓形成和再闭塞、全身性炎症反应综合征（SIRS）、多器官功能障碍综合征（MODS）、体外循环期间的血栓形成，或抽血时的血液凝结。
• Iron(0)-Mediated Reformatsky Reaction for the Synthesis of β-Hydroxyl Carbonyl Compounds
  作者：Xuan-Yu Liu、Xiang-Rui Li、Chen Zhang、Xue-Qiang Chu、Weidong Rao、Teck-Peng Loh、Zhi-Liang Shen

  DOI：10.1021/acs.orglett.9b01999

  日期：2019.8.2

  An efficient, economical, and practical Reformatsky reaction of α-halo carbonyl compounds with aldehydes/ketones by using cheap and commercial iron(0) powder as reaction mediator is developed. The reactions proceeded effectively in the presence of a catalytic amount of iodine (20 mol %) to afford the synthetically useful β-hydroxyl carbonyl compounds in moderate to good yields.

  通过使用廉价的市售铁（0）粉末作为反应介质，开发了α-卤代羰基化合物与醛/酮的高效，经济和实用的Reformatsky反应。该反应在催化量的碘（20mol％）的存在下有效地进行，以中等至良好的产率提供了合成上有用的β-羟基羰基化合物。
• 一种制备β-羟基羰基化合物的方法
  申请人：盐城师范学院

  公开号：CN110105212B

  公开（公告）日：2022-04-01

  本发明涉及一种制备β‑羟基羰基化合物的方法，主要提供了利用廉价的商业铁粉末介导的α‑卤代羰基化合物与醛/酮的反应，以提供相应的β‑羟基羰基化合物的方法。该工艺产率良好，具有宽的官能团耐受性和良好的相容性。
• Cp2ZrCl2-induced Reformatsky and Barbier reactions on isatins: an efficient synthesis of 3-substituted-3-hydroxyindolin-2-ones
  作者：Mangilal Chouhan、Ratnesh Sharma、Vipin A. Nair

  DOI：10.1002/aoc.1789

  日期：2011.6

  rapid one‐pot process for Reformatsky and Barbier reactions using a catalytic quantity of zirconocene dichloride (Cp2ZrCl2) as a promoter and zinc as a terminal reductant at room temperature in dimethyl formamide was developed. The protocol has wide substrate suitability and afforded the desired 3‐substituted‐3‐hydroxyindolin‐2‐ones from istains in good yields and short reaction time. Copyright © 2011

  开发了一种温和快速的一锅法，用于Reformatsky和Barbier反应，该方法使用催化量的二氯化锆（Cp 2 ZrCl 2）作为促进剂，锌在室温下的二甲基甲酰胺中作为末端还原剂。该方案具有广泛的底物适用性，并从玉米中获得了所需的3-取代-3-羟基吲哚-2-酮，收率高且反应时间短。版权所有©2011 John Wiley＆Sons，Ltd.
• Access to β-Hydroxyl Esters via Copper-Catalyzed Reformatsky Reaction of Ketones and Aldehydes
  作者：Ren Shi Luo、Lu Ouyang、Jian Hua Liao、Yan Ping Xia

  DOI：10.1055/s-0040-1707110

  日期：2020.9

  An efficient and simple Cu-catalyzed Reformatsky reaction of ketones and aldehydes has been accomplished with ethyl iodoacetate. Excellent yields of β-hydroxyl esters were achieved with a range of ketones and aldehydes, which varied from aromatic to aliphatic, unsaturated to saturated ketones and aldehydes. This practical and convenient transformation was conducted with inexpensive, readily available

  用碘乙酸乙酯完成了一种有效且简单的铜催化的酮和醛的 Reformatsky 反应。使用一系列酮和醛（从芳香族到脂肪族、从不饱和到饱和的酮和醛）可实现出色的 β-羟基酯收率。这种实用且方便的转化是在温和的反应条件下使用廉价、容易获得和商业化的原料进行的。

表征谱图