1-[(S)-6-Hydroxy-4-(6-hydroxy-naphthalen-2-yl)-3,4-dihydro-1H-isoquinolin-2-yl]-ethanone | 133043-31-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: 1-[(S)-6-Hydroxy-4-(6-hydroxy-naphthalen-2-yl)-3,4-dihydro-1H-isoquinolin-2-yl]-ethanone
• CAS: 133043-31-9
• 化学式: C₂₁H₁₉NO₃
• 分子量: 333.387
• InChiKey: BLCJLIBHUXPQTJ-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.75
• 重原子数：
  25.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  60.77
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-[(S)-6-Hydroxy-4-(6-hydroxy-naphthalen-2-yl)-3,4-dihydro-1H-isoquinolin-2-yl]-ethanone 在 caesium carbonate 、 cesium fluoride 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 144.0h， 生成 (S)-(+)-1,2-diacetyl-1',2',3',8',9',10',11'.23',24',25',26',35'a-dodecahydro-14',20',38',41'-tetramethylspirotrietheno<28,32:31,35>dimetheno<17H><1,6,16,21>tetraoxacyclotritriacontino<25,24-c>pyridine>
  参考文献：
  名称：

  Synthesis and complexation properties of a water-soluble optically active cyclophane incorporating a 4-naphthyl-1,2,3,4-tetrahydroisoquinoline unit as a chiral spacer

  摘要：

  The unnatural alkaloid 6-methoxy-4-[2-(6-methoxynaphthalenyl)]-1,2,3,4-tetrahydroisoquinoline (5) was prepared as a chiral spacer for optically active cyclophane receptors. Optical resolution of the building block was accomplished through diastereomeric salt formation with dibenzoyltartaric acid. The S configuration was assigned by X-ray crystallographic methods to the hydrochloride salt of (-)-5. Starting from enantiomerically pure 5, the optically active cyclophanes (R)- and (S)-4 were prepared. These cycophanes, in which the chiral alkaloid spacer is bridged to an achiral diphenylmethane unit, are efficient binders of napthalene derivatives in D2O/CD3OD (60:40, v/v) and show a modest degree of chiral recognition in the inclusion complexation of naproxen derivatives.

  DOI：

  10.1021/jo00010a034
• 作为产物：
  描述：

  2-溴-6-甲氧基萘 在 盐酸 、 sodium tetrahydroborate 、 18-冠醚-6 、 硼烷 、 sodium acetate 、 三溴化硼 、 magnesium 、 溶剂黄146 、 calcium chloride 、 三氯氧磷 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 乙腈 、 苯 为溶剂， 反应 227.0h， 生成 1-[(S)-6-Hydroxy-4-(6-hydroxy-naphthalen-2-yl)-3,4-dihydro-1H-isoquinolin-2-yl]-ethanone
  参考文献：
  名称：

  Synthesis and complexation properties of a water-soluble optically active cyclophane incorporating a 4-naphthyl-1,2,3,4-tetrahydroisoquinoline unit as a chiral spacer

  摘要：

  The unnatural alkaloid 6-methoxy-4-[2-(6-methoxynaphthalenyl)]-1,2,3,4-tetrahydroisoquinoline (5) was prepared as a chiral spacer for optically active cyclophane receptors. Optical resolution of the building block was accomplished through diastereomeric salt formation with dibenzoyltartaric acid. The S configuration was assigned by X-ray crystallographic methods to the hydrochloride salt of (-)-5. Starting from enantiomerically pure 5, the optically active cyclophanes (R)- and (S)-4 were prepared. These cycophanes, in which the chiral alkaloid spacer is bridged to an achiral diphenylmethane unit, are efficient binders of napthalene derivatives in D2O/CD3OD (60:40, v/v) and show a modest degree of chiral recognition in the inclusion complexation of naproxen derivatives.

  DOI：

  10.1021/jo00010a034