9,11,12,13,13a,14-hexahydro-2,3,6-trimethoxy-13a-methyldibenzo[f,h]pyrrolo[1,2-b]isoquinolin-11-one | 958261-83-1

• 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: 9,11,12,13,13a,14-hexahydro-2,3,6-trimethoxy-13a-methyldibenzo[f,h]pyrrolo[1,2-b]isoquinolin-11-one
• 英文别名: 2,3,6-Trimethoxy-13a-methyl-9,12,13,14-tetrahydrophenanthro[9,10-f]indolizin-11-one；2,3,6-trimethoxy-13a-methyl-9,12,13,14-tetrahydrophenanthro[9,10-f]indolizin-11-one
• CAS: 958261-83-1
• 化学式: C₂₄H₂₅NO₄
• 分子量: 391.467
• InChiKey: CCLVFPSLXAWVLY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  9,11,12,13,13a,14-hexahydro-2,3,6-trimethoxy-13a-methyldibenzo[f,h]pyrrolo[1,2-b]isoquinolin-11-one 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以96%的产率得到9,11,12,13,13a,14-hexahydro-2,3,6-trimethoxy-13a-methyldibenzo[f,h]pyrrolo[1,2-b]isoquinoline
  参考文献：
  名称：

  Total Synthesis of Phenanthroindolizidine Alkaloids through an Amidyl Radical Cascade/Rearrangement Reaction

  摘要：

  A short and general synthesis of the phenanthroindolizidine alkaloids is reported, featuring an unusual amidyl radical 5-exo/5-exo/rearrangement cascade of a xanthate precursor. Second, using an amidyl radical 5-exo/6-endo cascade to synthesize a phenanthroindolizidine alkaloid exclusively has been developed through a small structural modification.

  DOI：

  10.1021/ol4025925
• 作为产物：
  描述：

  4-甲基-4-戊酸 在 4-二甲氨基吡啶 、 草酰氯 、 过氧化双月桂酰 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 8.0h， 生成 9,11,12,13,13a,14-hexahydro-2,3,6-trimethoxy-13a-methyldibenzo[f,h]pyrrolo[1,2-b]isoquinolin-11-one
  参考文献：
  名称：

  Total Synthesis of Phenanthroindolizidine Alkaloids through an Amidyl Radical Cascade/Rearrangement Reaction

  摘要：

  A short and general synthesis of the phenanthroindolizidine alkaloids is reported, featuring an unusual amidyl radical 5-exo/5-exo/rearrangement cascade of a xanthate precursor. Second, using an amidyl radical 5-exo/6-endo cascade to synthesize a phenanthroindolizidine alkaloid exclusively has been developed through a small structural modification.

  DOI：

  10.1021/ol4025925

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.
• Total Synthesis of Phenanthroindolizidine Alkaloids through an Amidyl Radical Cascade/Rearrangement Reaction
  作者：Guifang Han、Yuxiu Liu、Qingmin Wang

  DOI：10.1021/ol4025925

  日期：2013.10.18

  A short and general synthesis of the phenanthroindolizidine alkaloids is reported, featuring an unusual amidyl radical 5-exo/5-exo/rearrangement cascade of a xanthate precursor. Second, using an amidyl radical 5-exo/6-endo cascade to synthesize a phenanthroindolizidine alkaloid exclusively has been developed through a small structural modification.