methyl 3-benzyl-1-hydroxy-2-naphthoate | 1384880-03-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl 3-benzyl-1-hydroxy-2-naphthoate
• 英文别名: 2-Naphthalenecarboxylic acid, 1-hydroxy-3-(phenylmethyl)-, methyl ester；methyl 3-benzyl-1-hydroxynaphthalene-2-carboxylate
• CAS: 1384880-03-8
• 化学式: C₁₉H₁₆O₃
• 分子量: 292.334
• InChiKey: XXYZXAFRTXGVNV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (E)-methyl 3-(3-cinnamylphenyl)-3-oxopropanoate 在 palladium(II) trifluoroacetate 、 copper diacetate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 23.0h， 以64%的产率得到methyl 3-benzyl-1-hydroxy-2-naphthoate
  参考文献：
  名称：

  Pd-Catalyzed Sequential C–C Bond Formation and Cleavage: Evidence for an Unexpected Generation of Arylpalladium(II) Species

  摘要：

  A Pd(II)-catalyzed reaction engaging alkenyl beta-keto esters is reported that leads to the formation of 1-naphthols and an unexpected generation of arylpalladium-(II) species. Interception of the in situ generated arylpalladium(II) species in a Mizoroki-Heck reaction, together with additional mechanistic studies, provided strong evidence in support of the first aromatization-driven beta-carbon elimination process. A single Pd catalyst served to promote a series of both C-C bond forming and cleavage events in an unprecedented manner.

  DOI：

  10.1021/ja304616q

文献信息

• Pd-Catalyzed Sequential C–C Bond Formation and Cleavage: Evidence for an Unexpected Generation of Arylpalladium(II) Species
  作者：So Won Youn、Byung Seok Kim、Arun R. Jagdale

  DOI：10.1021/ja304616q

  日期：2012.7.18

  A Pd(II)-catalyzed reaction engaging alkenyl beta-keto esters is reported that leads to the formation of 1-naphthols and an unexpected generation of arylpalladium-(II) species. Interception of the in situ generated arylpalladium(II) species in a Mizoroki-Heck reaction, together with additional mechanistic studies, provided strong evidence in support of the first aromatization-driven beta-carbon elimination process. A single Pd catalyst served to promote a series of both C-C bond forming and cleavage events in an unprecedented manner.