5-Methoxy-4-methyl-1-pyridin-2-ylsulfonylindole-3-carbaldehyde | 1443501-78-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 5-Methoxy-4-methyl-1-pyridin-2-ylsulfonylindole-3-carbaldehyde
• 英文别名: 5-methoxy-4-methyl-1-pyridin-2-ylsulfonylindole-3-carbaldehyde
• CAS: 1443501-78-7
• 化学式: C₁₆H₁₄N₂O₄S
• 分子量: 330.364
• InChiKey: FMILWPZTDZGOIR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  86.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-Methoxy-4-methyl-1-pyridin-2-ylsulfonylindole-3-carbaldehyde 在 indium 、 三苯基膦双(三氟甲磺酰亚胺)金 、 氯化铵 作用下， 以 四氢呋喃 、 水 、 1,2-二氯乙烷 为溶剂， 生成 5-Methoxy-4-methyl-3-(3-methyl-2,5-dihydrofuran-2-yl)-1-pyridin-2-ylsulfonylindole
  参考文献：
  名称：

  Carbocyclization versus Oxycyclization on the Metal-Catalyzed Reactions of Oxyallenyl C3-Linked Indoles

  摘要：

  The preparation of previously unknown (indol-3-yl)-alpha-allenols and -allenones was accomplished from indole-3-carbaldehydes, through indium mediated Barbier allenylation reaction taking advantage of the N-(2-pyridyl)sulfonyl group. Metal catalyzed cyclizations of oxyallenyl C3-linked indoles proceeded in two ways depending on the presence or absence of the N- (2-pyridyl)sulfonyl group. For allenols, gold catalyzed oxycyclization occurred in the presence of the protecting group; in the absence of the protecting group, palladium- and gold-catalyzed benzannulations operated. On the contrary, under gold catalysis furyl-indoles were obtained as exclusive products from NH-allenones, while S-endo carbocyclization adducts were the major components starting from N-SO(2)py-protected allenones. These cyclization reactions have been developed experimentally, and their mechanisms have additionally been investigated by a computational study.

  DOI：

  10.1021/jo401013d
• 作为产物：
  描述：

  吡啶-2-磺酰氯 、 5-甲氧基-4-甲基吲哚-3-甲醛 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以82%的产率得到5-Methoxy-4-methyl-1-pyridin-2-ylsulfonylindole-3-carbaldehyde
  参考文献：
  名称：

  Carbocyclization versus Oxycyclization on the Metal-Catalyzed Reactions of Oxyallenyl C3-Linked Indoles

  摘要：

  The preparation of previously unknown (indol-3-yl)-alpha-allenols and -allenones was accomplished from indole-3-carbaldehydes, through indium mediated Barbier allenylation reaction taking advantage of the N-(2-pyridyl)sulfonyl group. Metal catalyzed cyclizations of oxyallenyl C3-linked indoles proceeded in two ways depending on the presence or absence of the N- (2-pyridyl)sulfonyl group. For allenols, gold catalyzed oxycyclization occurred in the presence of the protecting group; in the absence of the protecting group, palladium- and gold-catalyzed benzannulations operated. On the contrary, under gold catalysis furyl-indoles were obtained as exclusive products from NH-allenones, while S-endo carbocyclization adducts were the major components starting from N-SO(2)py-protected allenones. These cyclization reactions have been developed experimentally, and their mechanisms have additionally been investigated by a computational study.

  DOI：

  10.1021/jo401013d

文献信息

• Carbocyclization versus Oxycyclization on the Metal-Catalyzed Reactions of Oxyallenyl C3-Linked Indoles
  作者：Benito Alcaide、Pedro Almendros、José M. Alonso、Israel Fernández

  DOI：10.1021/jo401013d

  日期：2013.7.5

  The preparation of previously unknown (indol-3-yl)-alpha-allenols and -allenones was accomplished from indole-3-carbaldehydes, through indium mediated Barbier allenylation reaction taking advantage of the N-(2-pyridyl)sulfonyl group. Metal catalyzed cyclizations of oxyallenyl C3-linked indoles proceeded in two ways depending on the presence or absence of the N- (2-pyridyl)sulfonyl group. For allenols, gold catalyzed oxycyclization occurred in the presence of the protecting group; in the absence of the protecting group, palladium- and gold-catalyzed benzannulations operated. On the contrary, under gold catalysis furyl-indoles were obtained as exclusive products from NH-allenones, while S-endo carbocyclization adducts were the major components starting from N-SO(2)py-protected allenones. These cyclization reactions have been developed experimentally, and their mechanisms have additionally been investigated by a computational study.