(S)-2-methoxymethyl-2,3-dihydro-1H-3a-aza-cyclopenta[a]indene-8-carboxaldehyde | 886883-42-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (S)-2-methoxymethyl-2,3-dihydro-1H-3a-aza-cyclopenta[a]indene-8-carboxaldehyde
• 英文别名: (2S)-2-(methoxymethyl)-2,3-dihydro-1H-pyrrolo[1,2-a]indole-4-carbaldehyde
• CAS: 886883-42-7
• 化学式: C₁₄H₁₅NO₂
• 分子量: 229.279
• InChiKey: DFHJMRDSJZRYPP-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-2-methoxymethyl-2,3-dihydro-1H-3a-aza-cyclopenta[a]indene-8-carboxaldehyde 在 [Rh(1,3-bis(diphenylphosphino)propane)₂]Cl 、 palladium diacetate 、 (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl potassium carbonate 、 caesium carbonate 作用下， 以 四氢呋喃 、 甲苯 、 xylene 为溶剂， 反应 146.0h， 生成 (S)-1-(2,4-dimethoxy-benzyl)-3-(2-methoxymethyl-2,3-dihydro-1H-3a-azacyclopenta[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：

  1-(2-methoxymethyl-allyl)-1H-indole-3-carboxaldehyde 在 (3,5-dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-(1-phenyl-ethyl)-amine 、 [RhCl(coe)2]2 溶剂黄146 作用下， 以 四氢呋喃 、 甲苯 、 苯 为溶剂， 反应 39.0h， 生成 (S)-2-methoxymethyl-2,3-dihydro-1H-3a-aza-cyclopenta[a]indene-8-carboxaldehyde
  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.