2-cyano-1-hydroxy-1,2-dihydroisoquinoline | 941-94-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚和异茚
• 英文名称: 2-cyano-1-hydroxy-1,2-dihydroisoquinoline
• 英文别名: 1-hydroxy-1H-isoquinoline-2-carbonitrile；1-Hydroxy-1H-isochinolin-2-carbonitril；2-Cyan-1-hydroxy-1,2-dihydro-isochinolin；1-hydroxy-1H-isoquinoline-2-carbonitrile
• CAS: 941-94-6
• 化学式: C₁₀H₈N₂O
• 分子量: 172.186
• InChiKey: LWAOSIWPROAMIS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  47.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-cyano-1-hydroxy-1,2-dihydroisoquinoline 在 sodium tetrahydroborate 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 为溶剂， 反应 28.0h， 生成 2-ethyl-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  2-氰基-1,2-二氢异喹啉与溴在甲醇中加和不加吡啶时的立体化学方面

  摘要：

  2-Cyano-1-methoxy-1,2-dihydroisoquinoline (3) treated with bromine in methanol gave 4-bromo-2-cyano-1,3-dimethoxy-1,2,3,4-tetrahydroisoquinolines (4) exhibiting two configurational isomers (4a and 4b). During repeated recrystallization of 4a, auto-hydrolysis led it to 1-demethylation product (6), whereas 4b was intact giving single crystals. The structures of 4b and 6a were determined by X-Ray crystallography. 2-Cyano-1-hydroxy-1,2-dihydroisoquinoline (7) treated with bromine in methanol containing pyridine gave 6a stereoselectively in high yield, whereas from 3 compounds (4a) and (4b) were afforded in a product ratio of 1 : 1. The mechanisms for the 4a and 4b interconvertible reaction and also for the reaction from 7 to 6a were examined.

  DOI：

  10.3987/com-99-8820
• 作为产物：
  描述：

  异喹啉 、 溴化氰 在 乙醚 作用下， 生成 2-cyano-1-hydroxy-1,2-dihydroisoquinoline 、 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  Shimidzu, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1926, p. 92

  摘要：

  DOI：