2-(4-氯苄基)-3-氧代-3-苯基丙酸乙酯 | 859189-07-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 中文名称: 2-(4-氯苄基)-3-氧代-3-苯基丙酸乙酯
• 英文名称: ethyl 2-(4-chlorobenzyl)-3-oxo-3-phenylpropanoate
• 英文别名: Ethyl 2-[(4-chlorophenyl)methyl]-3-oxo-3-phenylpropanoate
• CAS: 859189-07-4
• 化学式: C₁₈H₁₇ClO₃
• 分子量: 316.784
• InChiKey: NPPHHROMXZOEPP-UHFFFAOYSA-N

物化性质

• 熔点：
  54-55 °C
• 沸点：
  240 °C(Press: 12 Torr)
• 密度：
  1.202±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-氯苄基)-3-氧代-3-苯基丙酸乙酯 在 barium dihydroxide 作用下， 生成 3-(4-氯苯基)苯丙酮
  参考文献：
  名称：

  Burton; Ingold, Journal of the Chemical Society, 1928, p. 915

  摘要：

  DOI：
• 作为产物：
  描述：

  ethyl 2-benzoyl-3-(4-chlorophenyl)acrylate 在 二氢吡啶 、 N-((1R,2S)-(1-hydroxy-1,2-diphenylethan-2-yl))-N'-(3,5-bis-(trifluoro-methyl)-phenyl)-thiourea 作用下， 以 水 为溶剂， 反应 24.0h， 以92%的产率得到2-(4-氯苄基)-3-氧代-3-苯基丙酸乙酯
  参考文献：
  名称：

  硫脲在水中的Hantzsch酯作为还原剂催化α-酮基取代的丙烯酸酯化合物的还原†

  摘要：

  已开发出第一种在硫脲催化下在水中通过Hantzsch酯还原α-酮基取代的丙烯酸酯化合物的方法。分离出的产品具有中等至高收率（38–95％）。这些产物是合成一系列天然产物和其他生物活性分子的重要中间体。

  DOI：

  10.1039/c7ra00995j

文献信息

• Environmentally benign nucleophilic substitution reaction of arylalkyl halides in water using CTAB as the inverse phase transfer catalyst
  作者：Atul K. Godha、Jayaraman Thiruvengadam、Viswanadhan Abhilash、Prajwal Balgi、A. V. Narayanareddy、Kumaresan Vignesh、Amol V. Gadakh、A. M. Sathiyanarayanan、Sambasivam Ganesh

  DOI：10.1039/c9nj03941d

  日期：——

  An environmentally benign, practically scalable and highly selective C-arylalkylation of active methylene compounds is developed using CTAB as the inverse phase transfer catalyst in water. The methodology developed is elaborated into the one-pot synthesis of quinoline derivatives and also applicable to the regioselective N-aralkyl of 2-pyridones.

  使用CTAB作为水中的反相转移催化剂，开发了一种环境友好，实用可扩展且选择性高的活性亚甲基化合物的C-芳烷基化方法。所开发的方法详述于一锅合成喹啉衍生物中，并且也适用于2-吡啶酮的区域选择性N-芳烷基。
• Enantioselective and Diastereoselective Ir-Catalyzed Hydrogenation of α-Substituted β-Ketoesters via Dynamic Kinetic Resolution
  作者：Guoxian Gu、Jiaxiang Lu、Ouran Yu、Jialin Wen、Qin Yin、Xumu Zhang

  DOI：10.1021/acs.orglett.8b00433

  日期：2018.4.6

  An iridium/f-amphol catalytic system for the enantioselective hydrogenation of α-substituted β-ketoesters via dynamic kinetic resolution is reported. The desired anti products were obtained in high yields (up to 98%) with good diastereoselectivity (up to 96:4 diastereometic ratio (dr)) and excellent enantioselectivity (up to >99% enantiomeric excess (ee)). A catalytic model is proposed to explain the

  报道了用于通过动态动力学拆分对α-取代的β-酮酸酯进行对映选择性氢化的铱/ f-amphol催化体系。以高收率（高达98％），良好的非对映选择性（高达96：4的非对映比率（dr））和优异的对映选择性（高达> 99％的对映体过量（ee））获得所需的抗产物。提出了催化模型来解释立体选择性。
• Highly chemoselective transfer hydrogenation of the C C bonds of α-Keto substituted acrylate compounds catalyzed by an Iridium-TsEN complex in water
  作者：Ala' Ahmad、Crystal Wong、Jordan Chapin、Bukuo Ni

  DOI：10.1016/j.tetlet.2023.154904

  日期：2024.1

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• A Convenient and Efficient Synthesis of Dipeptidyl Benzoxaboroles and Their Peptidomimetics
  作者：Zhengyan Fu、Yongmei Xie、Jiangpeng He、Aiping Tong、Yuquan Wei

  DOI：10.1055/s-0033-1339550

  日期：——

  We have developed a convenient and efficient method for the synthesis of dipeptidyl benzoxaboroles and their peptidomimetics. The novel dipeptidyl benzoxaboroles were obtained by the protecting-group-free coupling of 6-amino-1,3-dihydro-2,1-benzoxaborol-1-ol with various N-(arylcarbonyl)phenylalanines. Bioisosteric replacement of the terminal amide moiety of dipeptidyl benzoxaboroles by 1,3,4-oxadiazoles or 4H-3,1-benzothiazin-4-one provided their peptidomimetics with good molecular diversity. These transformations were based on the pluripotency of methyl (S)-2-isothiocyanato-3-phenylpropanoate and were highlighted by mild reaction conditions, high atom efficiency, and good to excellent isolated yields. This method is a valuable addition to the development of novel drug-like boronic acid molecules.
• Regioselective Palladium(II)-Catalyzed Desulfitative Heck-Type Reaction: Access to α-Benzyl-β-keto Esters from Baylis-Hillman Adducts and Sodium Sulfinates
  作者：Kommu Nagaiah、Kammari Bal Raju、Vellakkaran Mari

  DOI：10.1055/s-0033-1339663

  日期：——

  A new palladium(II)-catalyzed desulfitative Heck-Type arylation from sodium arenesulfinates and Baylis-Hillman adducts for the synthesis of highly functionalized alpha-benzyl-beta-keto ester derivatives in good to excellent yields has been developed. This methodology is simple and mild, it can utilize halogen bearing building blocks, and it has excellent regioselectivity.