1-(3-Methoxyphenyl)-2-(4-methylphenyl)sulfonyl-1,3,4,9-tetrahydropyrido[3,4-b]indole | 1112426-46-6

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: 1-(3-Methoxyphenyl)-2-(4-methylphenyl)sulfonyl-1,3,4,9-tetrahydropyrido[3,4-b]indole
• CAS: 1112426-46-6
• 化学式: C₂₅H₂₄N₂O₃S
• 分子量: 432.543
• InChiKey: CWUYFWKSKUTIAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  70.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(3-Methoxyphenyl)-2-(4-methylphenyl)sulfonyl-1,3,4,9-tetrahydropyrido[3,4-b]indole 在 sodium hydroxide 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 0.5h， 以93%的产率得到1-(3-methoxyphenyl)-4,9-dihydro-3H-pyrido[3,4-b]indole
  参考文献：
  名称：

  Mild and Efficient Syntheses of 1-Aryl-3,4-dihydroisoquinolines and 1-Aryl-3,4-dihydro-β-carbolines via Regiospecific β-Eliminations of the CorrespondingN-Tosyl-1,2,3,4-tetrahydroisoquinolines andN-Tosyl-1,2,3,4-tetrahydro-β-carbolines

  摘要：

  Treatment of N-tosyl-1-aryl-1,2,3,4-tetrahydro-isoquinolines or N-tosyl-1-aryl-1, 2,3,4-tetrahydro-beta-carbolines with a strong base such as NaOH or KOH at 70 degrees C in dimethylsulfoxide (DMSO) produced 1-aryl-3,4-dihydroisoquinolines or 1-aryl-3,4-dihydro-beta-carbolines in good yields via mild and regiospecific beta-eliminations. A dramatic solvent effect was observed, DMSO was crucial for the reactions. The temperature is also crucial for the reactions and should be kept between 60 and 80 degrees C.

  DOI：

  10.1080/00397911.2011.568659
• 作为产物：
  描述：

  对甲苯磺酰氯 、 1-(3-methoxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole 在 吡啶 、 potassium carbonate 作用下， 生成 1-(3-Methoxyphenyl)-2-(4-methylphenyl)sulfonyl-1,3,4,9-tetrahydropyrido[3,4-b]indole
  参考文献：
  名称：

  Mild and Efficient Syntheses of 1-Aryl-3,4-dihydroisoquinolines and 1-Aryl-3,4-dihydro-β-carbolines via Regiospecific β-Eliminations of the CorrespondingN-Tosyl-1,2,3,4-tetrahydroisoquinolines andN-Tosyl-1,2,3,4-tetrahydro-β-carbolines

  摘要：

  Treatment of N-tosyl-1-aryl-1,2,3,4-tetrahydro-isoquinolines or N-tosyl-1-aryl-1, 2,3,4-tetrahydro-beta-carbolines with a strong base such as NaOH or KOH at 70 degrees C in dimethylsulfoxide (DMSO) produced 1-aryl-3,4-dihydroisoquinolines or 1-aryl-3,4-dihydro-beta-carbolines in good yields via mild and regiospecific beta-eliminations. A dramatic solvent effect was observed, DMSO was crucial for the reactions. The temperature is also crucial for the reactions and should be kept between 60 and 80 degrees C.

  DOI：

  10.1080/00397911.2011.568659