2-[Hydroxy-(4-methoxyphenyl)methyl]-1-methylindole-3-carbaldehyde | 154989-52-3

• 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: 2-[Hydroxy-(4-methoxyphenyl)methyl]-1-methylindole-3-carbaldehyde
• CAS: 154989-52-3
• 化学式: C₁₈H₁₇NO₃
• 分子量: 295.338
• InChiKey: QWLODIQKSBEBIC-UHFFFAOYSA-N

物化性质

• 沸点：
  534.5±50.0 °C(predicted)
• 密度：
  1.19±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  51.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[Hydroxy-(4-methoxyphenyl)methyl]-1-methylindole-3-carbaldehyde 在 乙酸铵 作用下， 以 溶剂黄146 为溶剂， 反应 12.0h， 以32%的产率得到3-(4-methoxyphenyl)-1-[3-(4-methoxyphenyl)-4-methylpyrrolo[3,4-b]indol-2-yl]-4-methylfuro[3,4-b]indole
  参考文献：
  名称：

  Indolecarbonyl Coupling Reactions Promoted by Samarium Diiodide. Application to the Synthesis of Indole-Fused Compounds

  摘要：

  By the assistance of an N-sulfonyl group or a cyano group at the C-2 position, hydroxyalkylations of indole-3-carbonyls were achieved by the promotion of samarium diiodide. The indolecarbonyl coupling reactions proceeded in high stereoselectivity via chelate transition states. Intramolecular indolecarbonyl couplings of 1-(3-oxopropyl)indole-3-carboxaldehydes were realized as the indole-carbonyl group was more reactive toward SmI2 than the aliphatic carbonyl group. Elaboration of the coupling products with oxidizing agents, acid, phosphorus pentasulfide (or Lawesson's reagent), amines, and hydrazine led to a variety of indole derivatives and indole-fused polycyclic compounds of synthetic interest and pharmaceutical uses.

  DOI：

  10.1021/jo9720795
• 作为产物：
  描述：

  4-甲氧基苯甲醛 、 3-甲酰基-1-甲基吲哚-2-甲腈 在 六甲基磷酰三胺 、 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以82%的产率得到2-[Hydroxy-(4-methoxyphenyl)methyl]-1-methylindole-3-carbaldehyde
  参考文献：
  名称：

  Samarium(II) iodide-promoted hydroxyalkylations of indole 3-carbonyls. An expedient approach to pyrrolidino[1,2-a]indoles and furo[3,4-b]indoles

  摘要：

  在助溶剂六甲基磷酰胺存在下，3-甲酰基-、3-乙酰基-1-甲基吲哚及其 2-氰基类似物在碘化钐（II）的处理下发生分子内和分子间羟烷基化反应；分子内偶联产物具有霉菌素的结构原型，分子间偶联产物很容易转化为呋喃吲哚，作为吲哚-2,3-喹啉二甲醚的合成等价物。

  DOI：

  10.1039/c39930001277

文献信息

• Samarium(II) iodide-promoted hydroxyalkylations of indole 3-carbonyls. An expedient approach to pyrrolidino[1,2-a]indoles and furo[3,4-b]indoles
  作者：Jiann-Shyng Shiue、Jim-Min Fang

  DOI：10.1039/c39930001277

  日期：——

  3-Formyl-, 3-acetyl-1-methylindole and their 2-cyano analogues undergo intra- and inter-molecular hydroxyalkylations on treatment with samarium(II) iodide in the presence of a cosolvent hexamethylphosphoramide; the intramolecular coupling products have the structure prototype of mytomycins and the intermolecular coupling products are readily converted to furoindoles as synthetic equivalents of indole-2,3-quinodimethanes.

  在助溶剂六甲基磷酰胺存在下，3-甲酰基-、3-乙酰基-1-甲基吲哚及其 2-氰基类似物在碘化钐（II）的处理下发生分子内和分子间羟烷基化反应；分子内偶联产物具有霉菌素的结构原型，分子间偶联产物很容易转化为呋喃吲哚，作为吲哚-2,3-喹啉二甲醚的合成等价物。
• Indolecarbonyl Coupling Reactions Promoted by Samarium Diiodide. Application to the Synthesis of Indole-Fused Compounds
  作者：Shu-Chen Lin、Fwu-Duo Yang、Jiann-Shyng Shiue、Shyh-Ming Yang、Jim-Min Fang

  DOI：10.1021/jo9720795

  日期：1998.5.1

  By the assistance of an N-sulfonyl group or a cyano group at the C-2 position, hydroxyalkylations of indole-3-carbonyls were achieved by the promotion of samarium diiodide. The indolecarbonyl coupling reactions proceeded in high stereoselectivity via chelate transition states. Intramolecular indolecarbonyl couplings of 1-(3-oxopropyl)indole-3-carboxaldehydes were realized as the indole-carbonyl group was more reactive toward SmI2 than the aliphatic carbonyl group. Elaboration of the coupling products with oxidizing agents, acid, phosphorus pentasulfide (or Lawesson's reagent), amines, and hydrazine led to a variety of indole derivatives and indole-fused polycyclic compounds of synthetic interest and pharmaceutical uses.