ethyl 3-hydroxy-5-phenylpent-4-enoate | 26954-29-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: ethyl 3-hydroxy-5-phenylpent-4-enoate
• 英文别名: ethyl 3-hydroxy-5-phenyl-1-pent-4-enoate；Ethyl 3-hydroxy-5-phenylpent-4-enoate
• CAS: 26954-29-0
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: GKJRUOHBIQZQNO-UHFFFAOYSA-N

物化性质

• 沸点：
  365.0±30.0 °C(Predicted)
• 密度：
  1.113±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 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-5-phenylpent-4-enoate 在 4-二甲氨基吡啶 、 immobilized Candida parapsilosis ATCC 7330 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 7.5h， 生成 (E)-(S)-5-Phenyl-3-((S)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-pent-4-enoic acid ethyl ester
  参考文献：
  名称：

  Deracemisation of aromatic β-hydroxy esters using immobilised whole cells of Candida parapsilosis ATCC 7330 and determination of absolute configuration by 1H NMR

  摘要：

  Deracemisation of aryl and substituted aryl P-hydroxy esters using immobilised whole cells of Candida parapsilosis ATCC 7330 yields the corresponding (S)-enantiomer in >99% enantiomeric excess and good yield (up to 68%). The absolute configuration of ethyl 3-(2,4-dichlorophenyl)-3-hydroxy propanoate and ethyl 3-hydroxy-5-phenyl-pent-4-enoate as determined by H-1 NMR using MTPA chloride was found to be 'S'. The chemical shifts of the methoxy groups of the two diastereomeric MTPA esters were used as diagnostic signals to determine the absolute configuration. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.07.017
• 作为产物：
  描述：

  肉桂醛 、 碘代醋酸乙酯 在 nickel(II) iodide 、 锰 、 三氟乙酸 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以94%的产率得到ethyl 3-hydroxy-5-phenylpent-4-enoate
  参考文献：
  名称：

  一种β-羟基酯类化合物的合成方法

  摘要：

  本发明属于医药、有机化工合成技术领域，公开了一种β‑羟基酯类化合物的合成方法，以醛类化合物和碘代乙酸酯类化合物作为原料，锰粉作为促进剂，金属镍盐作为催化剂，以有机溶剂为反应介质，并加入有机质子酸，在惰性气体保护下搅拌反应，反应结束后冷却至室温，减压蒸馏浓缩得到粗产物，再经柱层析提纯，得到β‑羟基酯类化合物。本发明的合成方法操作安全简单，原料容易得到、价格低廉，反应效率高，产率可达到90％以上，甚至高达98％；对功能团适应性好，对底物适应性广，环境友好，有利于工业生产，在医药、有机合成中应用广泛。

  公开号：

  CN111333507B

文献信息

• Dimethylzinc-Mediated, Oxidatively Promoted Reformatsky Reaction of Ethyl Iodoacetate with Aldehydes and Ketones
  作者：Pier Giorgio Cozzi、Alessandro Mignogna、Paola Vicennati

  DOI：10.1002/adsc.200700572

  日期：2008.5.5

  A practical and general Reformatsky reaction, promoted by oxidants and mediated by dimethylzinc, is described. The reaction is fast and runs at 0 °C with aldehydes and ketones, under mild reaction conditions. Preliminary results obtained for the enantioselective version show that inexpensive chiral amino alcohols could be used in the challenging formation of enantioenriched quaternary stereogenic centers

  描述了一种由氧化剂促进并由二甲基锌介导的实用且通用的Reformatsky反应。该反应快速，可在温和的反应条件下于0°C与醛和酮一起运行。对映体选择性形式获得的初步结果表明，廉价的手性氨基醇可用于富挑战性地形成对映体富集的季立体异构中心。
• A Ball‐Milling‐Enabled Reformatsky Reaction
  作者：Qun Cao、Roderick T. Stark、Ian A. Fallis、Duncan L. Browne

  DOI：10.1002/cssc.201900886

  日期：2019.6.21

  An operationally simple one‐jar one‐step mechanochemical Reformatsky reaction using in situ generated organozinc intermediates under neat grinding conditions has been developed. Notable features of this reaction protocol are that it requires no solvent, no inert gases, and no pre‐activation of the bulk zinc source. The developed process is demonstrated to have good substrate scope (39–82 % yield) and

  已开发出一种在简单研磨条件下使用原位生成的有机锌中间体进行的简单操作的一罐式一步机械化学Reformatsky反应。该反应规程的显着特征是它不需要溶剂，不需要惰性气体并且无需预先激活大量的锌源。事实证明，开发的工艺具有良好的底物范围（39-82％的产率），并且不管锌源的初始形态如何都有效。
• Reformatsky Reaction in Water:  Evidence for a Radical Chain Process
  作者：Lothar W. Bieber、Ivani Malvestiti、Elisabeth C. Storch

  DOI：10.1021/jo970827k

  日期：1997.12.1

  The Reformatsky reaction of 2-bromo esters and carbonyl compounds in the presence of zinc can be carried out in concentrated aqueous salt solutions without any cosolvent. The reaction of bromoacetates is greatly enhanced by catalytic amounts of benzoyl peroxide or peracids and gives satisfactory yields with aromatic aldehydes. Preparative yields comparable to those of the traditional procedure are obtained with ethyl 2-bromoisobutyrate. This ester needs no catalyst and reacts even with saturated aldehydes and aromatic ketones, although in law yields. A radical chain mechanism, initiated by electron abstraction from the organometallic Reformatsky reagent, is proposed. Two nonchain pathways, involving radicals directly produced od the metal surface, may compete, especially in the case of secondary and tertiary halides.
• Lewis Acid Catalysis in Supercritical Carbon Dioxide. Use of Poly(ethylene glycol) Derivatives and Perfluoroalkylbenzenes as Surfactant Molecules Which Enable Efficient Catalysis in ScCO₂
  作者：Ichiro Komoto、Shū Kobayashi

  DOI：10.1021/jo0353177

  日期：2004.2.1

  Lewis acid catalysis in supercritical carbon dioxide (CO2) was investigated. While solubility of most organic materials is low in scCO(2), poly(ethylene glycol) derivatives or perfluoroalkylbenzenes were found to work as surfactants to dissolve organic materials in scCO(2). In the presence of these molecules, Lewis acid catalyzed organic reactions such as aldol-, Mannich-, and Friedel-Crafts-type reactions proceeded smoothly in scCO(2). Formation of emulsions was observed in these reactions, and the systems were studied in detail.
• 一种β-羟基酯类化合物的合成方法
  申请人：赣南医学院

  公开号：CN111333507B

  公开（公告）日：2022-10-18

  本发明属于医药、有机化工合成技术领域，公开了一种β‑羟基酯类化合物的合成方法，以醛类化合物和碘代乙酸酯类化合物作为原料，锰粉作为促进剂，金属镍盐作为催化剂，以有机溶剂为反应介质，并加入有机质子酸，在惰性气体保护下搅拌反应，反应结束后冷却至室温，减压蒸馏浓缩得到粗产物，再经柱层析提纯，得到β‑羟基酯类化合物。本发明的合成方法操作安全简单，原料容易得到、价格低廉，反应效率高，产率可达到90％以上，甚至高达98％；对功能团适应性好，对底物适应性广，环境友好，有利于工业生产，在医药、有机合成中应用广泛。