(S)-3-bromo-1-(2,4-dimethoxy-benzyl)-4-(2-methoxymethyl-2,3-dihydro-1H-3a-azacyclopenta[a]inden-8-yl)-pyrrole-2,5-dione | 886883-45-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-3-bromo-1-(2,4-dimethoxy-benzyl)-4-(2-methoxymethyl-2,3-dihydro-1H-3a-azacyclopenta[a]inden-8-yl)-pyrrole-2,5-dione
• 英文别名: 3-bromo-1-[(2,4-dimethoxyphenyl)methyl]-4-[(2S)-2-(methoxymethyl)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-4-yl]pyrrole-2,5-dione
• CAS: 886883-45-0
• 化学式: C₂₆H₂₅BrN₂O₅
• 分子量: 525.399
• InChiKey: VGPKSQUYURTINH-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  70
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-3-bromo-1-(2,4-dimethoxy-benzyl)-4-(2-methoxymethyl-2,3-dihydro-1H-3a-azacyclopenta[a]inden-8-yl)-pyrrole-2,5-dione 在 palladium diacetate 、 (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl 甲烷磺酸 、 caesium carbonate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 14.5h， 生成 (S)-3-(2-methoxymethyl-2,3-dihydro-1H-3a-aza-cyclopenta[a]inden-8-yl)-4-phenylamino-pyrrole-2,5-dione
  参考文献：
  名称：

  Enantioselective Synthesis of a PKC Inhibitor via Catalytic C−H Bond Activation

  摘要：

  The syntheses of two biologically active molecules possessing dihydropyrroloindole cores (1 and 2) were completed using rhodium-catalyzed imine-directed CA bond functionalization, with the second of these molecules containing a stereocenter that can be set with 90% ee during cyclization using chiral nonracemic phosphoramidite ligands. Catalytic decarbonylation and direct indole/maleimide coupling provide efficient access to 2.

  DOI：

  10.1021/ol060485h
• 作为产物：
  描述：

  3-甲氧基-2-氯甲基丙烯 在 (3,5-dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-(1-phenyl-ethyl)-amine 、 [Rh(1,3-bis(diphenylphosphino)propane)₂]Cl 、 [RhCl(coe)2]2 potassium carbonate 、 溶剂黄146 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 、 xylene 、 苯 为溶剂， 反应 183.0h， 生成 (S)-3-bromo-1-(2,4-dimethoxy-benzyl)-4-(2-methoxymethyl-2,3-dihydro-1H-3a-azacyclopenta[a]inden-8-yl)-pyrrole-2,5-dione
  参考文献：
  名称：

  Enantioselective Synthesis of a PKC Inhibitor via Catalytic C−H Bond Activation

  摘要：

  The syntheses of two biologically active molecules possessing dihydropyrroloindole cores (1 and 2) were completed using rhodium-catalyzed imine-directed CA bond functionalization, with the second of these molecules containing a stereocenter that can be set with 90% ee during cyclization using chiral nonracemic phosphoramidite ligands. Catalytic decarbonylation and direct indole/maleimide coupling provide efficient access to 2.

  DOI：

  10.1021/ol060485h

文献信息

• Enantioselective Synthesis of a PKC Inhibitor via Catalytic C−H Bond Activation
  作者：Rebecca M. Wilson、Reema K. Thalji、Robert G. Bergman、Jonathan A. Ellman

  DOI：10.1021/ol060485h

  日期：2006.4.1

  The syntheses of two biologically active molecules possessing dihydropyrroloindole cores (1 and 2) were completed using rhodium-catalyzed imine-directed CA bond functionalization, with the second of these molecules containing a stereocenter that can be set with 90% ee during cyclization using chiral nonracemic phosphoramidite ligands. Catalytic decarbonylation and direct indole/maleimide coupling provide efficient access to 2.