2-methyl-1-(1-(pyridin-2-ylsulfonyl)-5-(p-tolyl)-1H-indol-3-yl)buta-2,3-dien-1-ol | 1443501-86-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2-methyl-1-(1-(pyridin-2-ylsulfonyl)-5-(p-tolyl)-1H-indol-3-yl)buta-2,3-dien-1-ol
• CAS: 1443501-86-7
• 化学式: C₂₅H₂₂N₂O₃S
• 分子量: 430.527
• InChiKey: KDBZIDUZAYZGBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.01
• 重原子数：
  31.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  72.19
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-methyl-1-(1-(pyridin-2-ylsulfonyl)-5-(p-tolyl)-1H-indol-3-yl)buta-2,3-dien-1-ol 在 manganese(IV) oxide 、 三苯基膦双(三氟甲磺酰亚胺)金 作用下， 以 1,2-二氯乙烷 、 乙腈 为溶剂， 生成 3-(3-Methylfuran-2-yl)-5-(4-methylphenyl)-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 在 indium 、 sodium hydride 、 氯化铵 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 2-methyl-1-(1-(pyridin-2-ylsulfonyl)-5-(p-tolyl)-1H-indol-3-yl)buta-2,3-dien-1-ol
  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