2-(4-iodo-phenyl)-N-(methoxycarbonylmethyl)acrylamide | 1167996-52-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(4-iodo-phenyl)-N-(methoxycarbonylmethyl)acrylamide
• 英文别名: Methyl 2-[2-(4-iodophenyl)prop-2-enoylamino]acetate；methyl 2-[2-(4-iodophenyl)prop-2-enoylamino]acetate
• CAS: 1167996-52-2
• 化学式: C₁₂H₁₂INO₃
• 分子量: 345.137
• InChiKey: QNYMCGDWLBNUIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  一氧化碳 、 2-(4-iodo-phenyl)-N-(methoxycarbonylmethyl)acrylamide 、 DL-丙氨酸甲酯盐酸盐 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 ℃ 、4.0 MPa 条件下， 反应 24.0h， 以78%的产率得到2-(4-((1-(methoxycarbonyl)ethyl)aminoglyoxyloyl)phenyl)-N-(methoxycarbonylmethyl)-acrylamide
  参考文献：
  名称：

  Palladium-catalysed selective aminocarbonylation of 1′,4-diiodostyrene

  摘要：

  1'4-Diiodostyrene possessing both iodo-aryl and iodo-alkenyl functionalities was prepared and used as substrate in palladium-catalysed aminocarbonylation. The corresponding dicarboxamides were obtained as major products in high yields by using several amine nucleophiles including amino acid methyl esters. Due to the highly different reactivity of the two iodo-functionalities, the selective aminocarbonylation of the iodo-vinyl moiety was carried out at atmospheric carbon monoxide pressure resulting in the formation of 4-iodo-phenyl-acrylamides. The latter amides were used as Substrates in high pressure aminocarbonylation resulting in amide-ketocarboxamide type products. The latter functionality was formed via double Carbon monoxide insertion into the iodo-aryl bond. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.04.012
• 作为产物：
  描述：

  一氧化碳 、 甘氨酸甲酯盐酸盐 、 1-(4-fluorophenyl)-1-iodoethene 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 24.0h， 以89%的产率得到2-(4-iodo-phenyl)-N-(methoxycarbonylmethyl)acrylamide
  参考文献：
  名称：

  Palladium-catalysed selective aminocarbonylation of 1′,4-diiodostyrene

  摘要：

  1'4-Diiodostyrene possessing both iodo-aryl and iodo-alkenyl functionalities was prepared and used as substrate in palladium-catalysed aminocarbonylation. The corresponding dicarboxamides were obtained as major products in high yields by using several amine nucleophiles including amino acid methyl esters. Due to the highly different reactivity of the two iodo-functionalities, the selective aminocarbonylation of the iodo-vinyl moiety was carried out at atmospheric carbon monoxide pressure resulting in the formation of 4-iodo-phenyl-acrylamides. The latter amides were used as Substrates in high pressure aminocarbonylation resulting in amide-ketocarboxamide type products. The latter functionality was formed via double Carbon monoxide insertion into the iodo-aryl bond. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.04.012

文献信息

• Palladium-catalysed selective aminocarbonylation of 1′,4-diiodostyrene
  作者：Antal Szilágyi、Roland Farkas、Andrea Petz、László Kollár

  DOI：10.1016/j.tet.2009.04.012

  日期：2009.6

  1'4-Diiodostyrene possessing both iodo-aryl and iodo-alkenyl functionalities was prepared and used as substrate in palladium-catalysed aminocarbonylation. The corresponding dicarboxamides were obtained as major products in high yields by using several amine nucleophiles including amino acid methyl esters. Due to the highly different reactivity of the two iodo-functionalities, the selective aminocarbonylation of the iodo-vinyl moiety was carried out at atmospheric carbon monoxide pressure resulting in the formation of 4-iodo-phenyl-acrylamides. The latter amides were used as Substrates in high pressure aminocarbonylation resulting in amide-ketocarboxamide type products. The latter functionality was formed via double Carbon monoxide insertion into the iodo-aryl bond. (C) 2009 Elsevier Ltd. All rights reserved.