3-羟基-2-(4-氯苯基)丙烯酸乙酯 | 4383-55-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-羟基-2-(4-氯苯基)丙烯酸乙酯
• 英文名称: 3-hydroxy-2-(4-chlorophenyl)acrylic acid ethyl ester
• 英文别名: ethyl (Z)-2-(4-chlorophenyl)-3-hydroxyprop-2-enoate
• CAS: 4383-55-5
• 化学式: C₁₁H₁₁ClO₃
• 分子量: 226.66
• InChiKey: FKDFMJGLSRALAR-YFHOEESVSA-N

物化性质

• 熔点：
  53-54 °C
• 沸点：
  363.0±42.0 °C(Predicted)
• 密度：
  1.261±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  3-羟基-2-(4-氯苯基)丙烯酸乙酯 在 臭氧 作用下， 以 甲醇 为溶剂， 反应 0.25h， 以91%的产率得到4-氯苯甲酰甲酸乙酯
  参考文献：
  名称：

  芳基α-酮酯的便捷新合成

  摘要：

  摘要 α-酮酯的多种用途包括酶抑制剂 1 和抗炎剂 2。它们也是有机合成中的有用试剂。 3 迄今为止，合成这些化合物的最有效方法通常涉及有毒副产物，例如氢氰化物，4 或需要昂贵或高反应性的起始试剂，如取代乙炔醚。5 其他简单的合成方法收率适中，或对特定底物有效。6 现在，我们提出了一种制备芳基 a-酮酯的便捷方法最大限度地减少这些问题。

  DOI：

  10.1080/00397919908086470
• 作为产物：
  描述：

  ethyl 3-(4-chlorophenyl)-2-diazo-3-hydroxypropanoate 在 dirhodium tetraacetate 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.08h， 生成 3-羟基-2-(4-氯苯基)丙烯酸乙酯
  参考文献：
  名称：

  DBU-catalyzed condensation of acyldiazomethanes to aldehydes in water and a new approach to ethyl β-hydroxy α-arylacrylates

  摘要：

  DBU-catalyzed condensation of ethyl diazoacetate (EDA) with aldehydes in pure water afforded corresponding beta-hydroxy alpha-diazo carbonyl compounds. The beta-hydroxy group of the products was further converted into beta-siloxy group. The Rh(II)-catalyzed reaction of the beta-aryl beta-siloxy alpha-diazo carbonyl compounds gave 1,2-aryl shift products predominantly. The three-step transformation constitutes an efficient synthesis of ethyl beta-hydroxy alpha-arylacrylates. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.12.062

文献信息

• [EN] PROCESS FOR MAKING AMINO ACID COMPOUNDS<br/>[FR] PROCÉDÉ DE PRÉPARATION DE COMPOSÉS D'ACIDES AMINÉS
  申请人：GENENTECH INC

  公开号：WO2013173779A1

  公开（公告）日：2013-11-21

  The invention provides new processes for making and purifying amino acid compounds, which are useful in the preparation of AKT inhibitors used in the treatment of diseases such as cancer, including the compound (S)-2-(4-chlorophenyl)-1-(4-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazin-1-yl)-3-(isopropylamino)propan-1-one.

  这项发明提供了制备和纯化氨基酸化合物的新工艺，这些化合物在制备用于治疗癌症等疾病的AKT抑制剂中非常有用，包括化合物(S)-2-(4-氯苯基)-1-(4-((5R,7R)-7-羟基-5-甲基-6,7-二氢-5H-环戊[d]嘧啶-4-基)哌嗪-1-基)-3-(异丙基氨基)丙酮。
• Palladium(0)-catalyzed rearrangement of allyl enol ethers to form chiral quaternary carbon centers via asymmetric allylic alkylation
  作者：Nazim Uddin、Mizzanoor Rahaman、Eduardo Alberch、Sharif A. Asad、M. Mahmun Hossain

  DOI：10.1016/j.tetlet.2018.07.065

  日期：2018.9

  Herein we report the first palladium(0)-catalyzed asymmetric allylic alkylation (AAA) of allyl enol ether via π-allylpalladium intermediate using Trost chiral diphosphine. This unprecedented reaction produced very rare α-aryl quaternary aldehydes with multi-functional groups. The main novelty in the chemistry demonstrates that enol ethers can be used as precursors for π-allylpalladium intermediates

  在本文中，我们报告了使用Trost手性二膦酸酯通过π-烯丙基钯中间体，通过烯丙基烯醇醚进行的第一个钯（0）催化的烯丙基烯醇醚不对称烯丙基烷基化（AAA）。这种空前的反应产生了非常罕见的具有多官能团的α-芳基季醛。化学中的主要新颖性表明，烯醇醚可用作π-烯丙基钯中间体的前体，这一发现当然是罕见的，据我们所知，也许没有先例。已发现手性配体（R，R）-L3在此Pd-AAA反应中是最佳的，并与一系列类似物提供良好至极佳的收率（80–95％）和对映选择性（70–90％）。
• NEUROLOGICALLY ACTIVE COMPOUNDS
  申请人：Barnham Kevin Jeffrey

  公开号：US20100160346A1

  公开（公告）日：2010-06-24

  The present invention relates to neurologically-active compounds, processes for their preparation and their use as pharmaceutical or veterinary agents, in particular for the treatment of neurological conditions, more specifically neurodegenerative conditions such as Alzheimer's disease.

  本发明涉及神经活性化合物，其制备方法以及它们作为制药或兽医制剂的用途，特别是用于治疗神经系统疾病，更具体地说是神经退行性疾病，如阿尔茨海默病。
• PROCESS FOR MAKING AMINO ACID COMPOUNDS
  申请人：Genentech, Inc.

  公开号：US20150148559A1

  公开（公告）日：2015-05-28

  The invention provides new processes for making and purifying amino acid compounds, which are useful in the preparation of AKT inhibitors used in the treatment of diseases such as cancer, including the compound (S)-2-(4-chlorophenyl)-1-(4-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazin-1-yl)-3-(isopropylamino)propan-1-one.

  这项发明提供了制备和纯化氨基酸化合物的新工艺，这些化合物在制备用于治疗癌症等疾病的AKT抑制剂时非常有用，包括化合物(S)-2-(4-氯苯基)-1-(4-((5R,7R)-7-羟基-5-甲基-6,7-二氢-5H-环戊[d]嘧啶-4-基)哌嗪-1-基)-3-(异丙基氨基)丙酮。
• Iron Lewis Acid Catalyzed Reactions of Aromatic Aldehydes with Ethyl Diazoacetate:  Unprecedented Formation of 3-Hydroxy-2-arylacrylic Acid Ethyl Esters by a Unique 1,2-Aryl Shift
  作者：Syed J. Mahmood、M. Mahmun Hossain

  DOI：10.1021/jo972142q

  日期：1998.5.1

  The iron Lewis acid [eta(5)-(C5H5)Fe(CO)(2)(TKF)]BF4 (1) was found to catalyze reactions of ethyl diazoacetate (EDA) and aromatic aldehydes, yielding 3-hydroxy-2-arylacrylic acid ethyl esters and the corresponding B-keto esters. According to the literature, this is the first report of the formation of enol esters from EDA and aromatic aldehydes. The yield of the enol esters increased with electron-rich aldehydes. With 2,4-dimethoxybenzaldehyde the only product isolated was the corresponding enol ester in 80% yield. However, in the presence of electron-deficient aldehydes such as p-nitrobenzaldehyde, formation of enol ester decreased to 32%. The most unique feature of these reactions is that enol esters are formed by an unusual 1,2-aryl shift, from a possible intermediate 8, which in turn is formed from the reaction of the iron aldehyde complex 7 and EDA.