2-(1-naphthyl)acrylic acid isopropyl ester | 1173656-92-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(1-naphthyl)acrylic acid isopropyl ester
• CAS: 1173656-92-2
• 化学式: C₁₆H₁₆O₂
• 分子量: 240.302
• InChiKey: HHLPPHNZPWNLCV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  一氧化碳 、 异丙醇 、 1-(1-iodo-vinyl)-naphthalene 在 palladium diacetate 、 三乙胺 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 50.0 ℃ 、5.5 MPa 条件下， 反应 66.0h， 以63%的产率得到2-(1-naphthyl)acrylic acid isopropyl ester
  参考文献：
  名称：

  Synthesis of 2-naphthylacrylamides and 2-naphthylacrylates via homogeneous catalytic carbonylation of 1-iodo-1-naphthylethene derivatives

  摘要：

  Two highly reactive iodoalkenes (1-iodo-1-(2-naphthyl)ethene and 1-iodo-1-(1-naphthyl)ethene) were prepared from the corresponding acetonaphthone isomers via their hydrazones and used as substrates in palladium-catalysed carbonylations. Both iodoalkenyl substrates proved to be highly reactive in the presence of various N-nucleophiles and the corresponding N-substituted naphthylacrylamides were formed chemoselectively in nearly quantitative yields. High isolated yields (up to 93%) were achieved with all types of amines under mild reaction conditions. The alkoxycarbonylation of the above iodoalkenes resulted in esters of unexpectedly good isolated yields (up to 77%). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.04.056

文献信息

• Synthesis of 2-naphthylacrylamides and 2-naphthylacrylates via homogeneous catalytic carbonylation of 1-iodo-1-naphthylethene derivatives
  作者：Attila Takács、Roland Farkas、Andrea Petz、László Kollár

  DOI：10.1016/j.tet.2009.04.056

  日期：2009.6

  Two highly reactive iodoalkenes (1-iodo-1-(2-naphthyl)ethene and 1-iodo-1-(1-naphthyl)ethene) were prepared from the corresponding acetonaphthone isomers via their hydrazones and used as substrates in palladium-catalysed carbonylations. Both iodoalkenyl substrates proved to be highly reactive in the presence of various N-nucleophiles and the corresponding N-substituted naphthylacrylamides were formed chemoselectively in nearly quantitative yields. High isolated yields (up to 93%) were achieved with all types of amines under mild reaction conditions. The alkoxycarbonylation of the above iodoalkenes resulted in esters of unexpectedly good isolated yields (up to 77%). (C) 2009 Elsevier Ltd. All rights reserved.