butyl 2-benzyl-3-(4-bromophenyl)-3-oxopropanoate | 1407163-04-5

• 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 2-benzyl-3-(4-bromophenyl)-3-oxopropanoate
• CAS: 1407163-04-5
• 化学式: C₂₀H₂₁BrO₃
• 分子量: 389.289
• InChiKey: XHSDEHYHWSKDEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  、 1-{[19-氨基-7-(2-氨基-2-羰基乙基)-10-(3-氨基-3-羰基丙基)-16-(4-乙基苯甲基)-13-(1-甲基丙基)-6,9,12,15,18-五羰基-1,2-二硫杂-5,8,11,14,17-五氮杂环二十碳烷-4-基]羰基}脯氨酰亮氨酰甘氨酸酰胺 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 2-benzyl-3-(4-bromophenyl)-3-oxopropanoate
  参考文献：
  名称：

  A Convenient and Efficient Synthesis of Dipeptidyl Benzoxaboroles and Their Peptidomimetics

  摘要：

  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.

  DOI：

  10.1055/s-0033-1339550

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。
• Replacing a stoichiometric silver oxidant with air: ligated Pd(<scp>ii</scp>)-catalysis to β-aryl carbonyl derivatives with improved chemoselectivity
  作者：Mari Vellakkaran、Murugaiah M. S. Andappan、Nagaiah Kommu

  DOI：10.1039/c3gc42504e

  日期：——

  Air was employed as a green reoxidant of Pd(0), replacing stoichiometric and toxic silver salt, in the chelation-controlled Pd(ii)-modulated arylative enolization of prop-2-en-1-ols to acquire synthetically-important β-aryl carbonyl derivatives.

  空气被用作Pd（0）的绿色氧化剂，取代了化学计量且有毒的银盐，在以螯合控制的Pd（II）调控下进行的烯醇化反应中，将丙烯-1-醇芳基化，以获得具有合成重要性的β-芳基酮衍生物。
• 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.
• 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.