butyl 2-benzyl-3-oxooctanoate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: butyl 2-benzyl-3-oxooctanoate
• 英文别名: Butyl 2-benzyl-3-oxooctanoate
• 化学式: C₁₉H₂₈O₃
• 分子量: 304.43
• InChiKey: MAANSUASCPVSMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  22
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 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：

  Butyl 2-methylidene-3-oxooctanoate 、 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96%的产率得到butyl 2-benzyl-3-oxooctanoate
  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

• 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.