1-(morpholin-4-yl)-2-(1-naphthyl)propenone | 1173656-79-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(morpholin-4-yl)-2-(1-naphthyl)propenone
• 英文别名: 1-Morpholin-4-yl-2-naphthalen-1-ylprop-2-en-1-one；1-morpholin-4-yl-2-naphthalen-1-ylprop-2-en-1-one
• CAS: 1173656-79-5
• 化学式: C₁₇H₁₇NO₂
• 分子量: 267.327
• InChiKey: AXUJVYPROJLHBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  吗啉 、 一氧化碳 、 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 ℃ 、100.0 kPa 条件下， 反应 20.0h， 以88%的产率得到1-(morpholin-4-yl)-2-(1-naphthyl)propenone
  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.