N-acryloyl-N-[1-methylethenyl]-[9-bromo-2,3,6-trimethoxyphenanthren-10-yl]methylamine | 958261-96-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: N-acryloyl-N-[1-methylethenyl]-[9-bromo-2,3,6-trimethoxyphenanthren-10-yl]methylamine
• 英文别名: N-[(10-bromo-3,6,7-trimethoxyphenanthren-9-yl)methyl]-N-prop-1-en-2-ylprop-2-enamide
• CAS: 958261-96-6
• 化学式: C₂₄H₂₄BrNO₄
• 分子量: 470.363
• InChiKey: ADHSXZUZMKPYIL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-acryloyl-N-[1-methylethenyl]-[9-bromo-2,3,6-trimethoxyphenanthren-10-yl]methylamine 在 三正丁基氢锡 、 1,1'-偶氮(氰基环己烷) 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以36%的产率得到9,11,12,13,13a,14-hexahydro-3,6,7-trimethoxy-13a-methyldibenzo[f,h]pyrrolo[1,2-b]-isoquinolin-11-one
  参考文献：
  名称：

  Synthesis of 13a-methylphenanthroindolizidines using radical cascade cyclization: synthetic studies toward (±)-hypoestestatin 1

  摘要：

  A radical cascade involving 6-endo cyclization of aryl radicals generated from N-acryloyl-N-(1-methylethenyl)-9-bromophenanthren-10-ylmethylamines, followed by 5-endo-trig cyclization of the resulting alpha-amidoyl radicals afforded phenanthroindolizidines bearing a methyl substituent at the angular C13a position. 2,3,6-Trimethoxy derivative was synthesized by using this method, but its spectral data were not in accord with those of literature values reported for hypoestestatin 1. Further synthetic study toward hypoestestatin 1 is demonstrated. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.08.030
• 作为产物：
  描述：

  3,6,7-三甲氧基菲-9-羧酸 在 氯化亚砜 、 四甲基乙二胺 、 仲丁基锂 、 二异丁基氢化铝 、 碳酸氢钠 、 溶剂黄146 、 三乙胺 、 N,N-二甲基甲酰胺 、 间氯过氧苯甲酸 、 三氟乙酸 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 xylene 为溶剂， 反应 70.51h， 生成 N-acryloyl-N-[1-methylethenyl]-[9-bromo-2,3,6-trimethoxyphenanthren-10-yl]methylamine
  参考文献：
  名称：

  Synthesis of 13a-methylphenanthroindolizidines using radical cascade cyclization: synthetic studies toward (±)-hypoestestatin 1

  摘要：

  A radical cascade involving 6-endo cyclization of aryl radicals generated from N-acryloyl-N-(1-methylethenyl)-9-bromophenanthren-10-ylmethylamines, followed by 5-endo-trig cyclization of the resulting alpha-amidoyl radicals afforded phenanthroindolizidines bearing a methyl substituent at the angular C13a position. 2,3,6-Trimethoxy derivative was synthesized by using this method, but its spectral data were not in accord with those of literature values reported for hypoestestatin 1. Further synthetic study toward hypoestestatin 1 is demonstrated. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.08.030

文献信息

• Synthesis of 13a-methylphenanthroindolizidines using radical cascade cyclization: synthetic studies toward (±)-hypoestestatin 1
  作者：Kosuke Takeuchi、Atsuko Ishita、Jun-ichi Matsuo、Hiroyuki Ishibashi

  DOI：10.1016/j.tet.2007.08.030

  日期：2007.11

  A radical cascade involving 6-endo cyclization of aryl radicals generated from N-acryloyl-N-(1-methylethenyl)-9-bromophenanthren-10-ylmethylamines, followed by 5-endo-trig cyclization of the resulting alpha-amidoyl radicals afforded phenanthroindolizidines bearing a methyl substituent at the angular C13a position. 2,3,6-Trimethoxy derivative was synthesized by using this method, but its spectral data were not in accord with those of literature values reported for hypoestestatin 1. Further synthetic study toward hypoestestatin 1 is demonstrated. (c) 2007 Elsevier Ltd. All rights reserved.