methyl 2-benzyl-3-(4-chlorophenyl)-3-oxopropanoate

• 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: methyl 2-benzyl-3-(4-chlorophenyl)-3-oxopropanoate
• 化学式: C₁₇H₁₅ClO₃
• 分子量: 302.757
• InChiKey: FAAZDLXQAVHWSI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  methyl 2-benzyl-3-(4-chlorophenyl)-3-oxopropanoate 在 一水合肼 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以70%的产率得到4-benzyl-5-(4-chlorophenyl)-2,3-dihydro-1H-pyrazol-3-one
  参考文献：
  名称：

  Morita–Baylis–Hillman adducts as building blocks of heterocycles: a simple approach to 4-substituted pyrazolones, and mechanism investigation via ESI–MS(/MS)

  摘要：

  We describe herein an efficient approach for the preparation of 4-substituted 2,3-dihydro-1H-pyrazol-3-ones starting from Morita-Baylis-Hillman adducts. These heterocycles were obtained in two or three steps as single isomers with moderate to good overall yields. One efficient and alternative methodology for the synthesis of alpha-methyl-beta-ketoesters is also reported (up to 91 % yield). Additionally, the mechanism of formation of pyrazolones was investigated employing ESI-MS/MS reaction monitoring.

  DOI：

  10.1007/s00706-015-1427-6
• 作为产物：
  描述：

  4-碘苯酚 、 2-[(4-氯苯基)-羟基甲基]-丙烯酸甲酯 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以75%的产率得到methyl 2-benzyl-3-(4-chlorophenyl)-3-oxopropanoate
  参考文献：
  名称：

  Morita–Baylis–Hillman adducts as building blocks of heterocycles: a simple approach to 4-substituted pyrazolones, and mechanism investigation via ESI–MS(/MS)

  摘要：

  We describe herein an efficient approach for the preparation of 4-substituted 2,3-dihydro-1H-pyrazol-3-ones starting from Morita-Baylis-Hillman adducts. These heterocycles were obtained in two or three steps as single isomers with moderate to good overall yields. One efficient and alternative methodology for the synthesis of alpha-methyl-beta-ketoesters is also reported (up to 91 % yield). Additionally, the mechanism of formation of pyrazolones was investigated employing ESI-MS/MS reaction monitoring.

  DOI：

  10.1007/s00706-015-1427-6

文献信息

• Arylation of the Baylis-Hillman adducts
  作者：Deevi Basavaiah、Kannan Muthukumaran

  DOI：10.1016/s0040-4020(98)00200-2

  日期：1998.5

  Palladium catalyzed arylation of the Baylis-Hillman adducts, methyl 3-hydroxy-2-methylenealkanoates, has been described.

  已经描述了Baylis-Hillman加合物，3-羟基-2-亚甲基链烷酸甲酯的钯催化的芳基化。