6-methoxy-4-<2-(6-methoxynaphthalenyl)>-3,4-dihydroisoquinoline | 133043-18-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢异喹啉
• 英文名称: 6-methoxy-4-<2-(6-methoxynaphthalenyl)>-3,4-dihydroisoquinoline
• 英文别名: 6-methoxy-4-(6-methoxynaphthalen-2-yl)-3,4-dihydroisoquinoline
• CAS: 133043-18-2
• 化学式: C₂₁H₁₉NO₂
• 分子量: 317.387
• InChiKey: IZQTWOIRRRFHIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.42
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  30.82
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  6-methoxy-4-<2-(6-methoxynaphthalenyl)>-3,4-dihydroisoquinoline 在 sodium tetrahydroborate 、 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 60.0h， 生成 (S)-(-)-2-acetyl-6-methoxy-4-<2-(6-methoxynaphthalenyl)>-1,2,3,4-tetrahydroisoquinoline
  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 、 18-冠醚-6 、 硼烷 、 magnesium 、 溶剂黄146 、 calcium chloride 、 三氯氧磷 作用下， 以 四氢呋喃 、 乙腈 、 苯 为溶剂， 反应 159.0h， 生成 6-methoxy-4-<2-(6-methoxynaphthalenyl)>-3,4-dihydroisoquinoline
  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