butyl 3-(4-bromophenyl)-2-(4-methylbenzyl)-3-oxopropanoate | 1407163-05-6

• 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
• 英文名称: butyl 3-(4-bromophenyl)-2-(4-methylbenzyl)-3-oxopropanoate
• 英文别名: Butyl 3-(4-bromophenyl)-2-[(4-methylphenyl)methyl]-3-oxopropanoate
• CAS: 1407163-05-6
• 化学式: C₂₁H₂₃BrO₃
• 分子量: 403.316
• InChiKey: DPRFXMJFXLWXKB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(hydroxy(4-bromophenyl)methyl)acrylic acid butyl ester 、 sodium 4-methylbenzenesulfinate 在 copper dichloride 、 palladium dichloride 作用下， 以 1,4-二氧六环 为溶剂， 反应 8.0h， 以87%的产率得到butyl 3-(4-bromophenyl)-2-(4-methylbenzyl)-3-oxopropanoate
  参考文献：
  名称：

  Regioselective Palladium(II)-Catalyzed Desulfitative Heck-Type Reaction: Access to α-Benzyl-β-keto Esters from Baylis-Hillman Adducts and Sodium Sulfinates

  摘要：

  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.

  DOI：

  10.1055/s-0033-1339663

文献信息

• Ligated Regioselective PdII Catalysis to Access β-Aryl-Bearing Aldehydes, Ketones, and β-Keto Esters
  作者：Mari Vellakkaran、Murugaiah M. S. Andappan、Nagaiah Kommu

  DOI：10.1002/ejoc.201200770

  日期：2012.9

  arylative isomerization of allyl alcohols, a milder and regioselective access to the versatile building blocks β-aryl aldehydes and ketones was developed. This new and chelation-controlled protocol enabled the compatibility of wide range of functionalities to generate dihydrochalcones, α-benzyl-α′-alkyl acetones, dihydrocinnamaldehydes, and α-benzyl β-keto esters (from Baylis–Hillman adducts). A practical

  通过在 PdII 介导的烯丙醇芳基化异构化中使用配体，开发了一种更温和和区域选择性的通用构建块 β-芳基醛和酮。这种新的螯合控制方案使广泛的功能兼容，以生成二氢查耳酮、α-苄基-α'-烷基丙酮、二氢肉桂醛和 α-苄基 β-酮酯（来自 Baylis-Hillman 加合物）。还展示了普罗帕酮中间体的实用多克合成。
• 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.