N-formyl-2-<2-(6-methoxynaphthalenyl)>-2-(3-methoxyphenyl)ethylamine | 133043-17-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-formyl-2-<2-(6-methoxynaphthalenyl)>-2-(3-methoxyphenyl)ethylamine
• 英文别名: N-[2-(6-methoxynaphthalen-2-yl)-2-(3-methoxyphenyl)ethyl]formamide
• CAS: 133043-17-1
• 化学式: C₂₁H₂₁NO₃
• 分子量: 335.403
• InChiKey: NYVHAYUNFQXDHI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.73
• 重原子数：
  25.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  47.56
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-formyl-2-<2-(6-methoxynaphthalenyl)>-2-(3-methoxyphenyl)ethylamine 在 三氯氧磷 作用下， 以 乙腈 为溶剂， 反应 12.0h， 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
• 作为产物：
  描述：

  <2-(6-methoxynaphthalenyl)>(3-methoxyphenyl)acetonitrile 在 硼烷 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 13.5h， 生成 N-formyl-2-<2-(6-methoxynaphthalenyl)>-2-(3-methoxyphenyl)ethylamine
  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

文献信息

• 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
  作者：Taxiarchis M. Georgiadis、Millie M. Georgiadis、Francois Diederich

  DOI：10.1021/jo00010a034

  日期：1991.5

  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.