1-(2-methoxymethyl-allyl)-1H-indole-3-carboxaldehyde | 886883-35-8

• 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: 1-(2-methoxymethyl-allyl)-1H-indole-3-carboxaldehyde
• 英文别名: 1-[2-(Methoxymethyl)prop-2-enyl]indole-3-carbaldehyde；1-[2-(methoxymethyl)prop-2-enyl]indole-3-carbaldehyde
• CAS: 886883-35-8
• 化学式: C₁₄H₁₅NO₂
• 分子量: 229.279
• InChiKey: HTDAOLXOOFBQQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 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：

  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-((R)-1-phenyl-ethyl)-amine 、 [RhCl(coe)2]2 silica gel 作用下， 以 二氯甲烷 、 氘代甲苯 、 乙酸乙酯 、 苯 为溶剂， 反应 36.0h， 生成 (R)-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
• 作为产物：
  描述：

  3-甲氧基-2-氯甲基丙烯 、 3-吲哚甲醛 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以64%的产率得到1-(2-methoxymethyl-allyl)-1H-indole-3-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.