(R)-(+)-2-acetyl-6-(4-chlorobutoxy)-4-<6-(4-chlorobutoxy)-2-naphthalenyl>-1,2,3,4-tetrahydroisoquinoline | 133043-21-7

• 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: (R)-(+)-2-acetyl-6-(4-chlorobutoxy)-4-<6-(4-chlorobutoxy)-2-naphthalenyl>-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 1-[(4R)-6-(4-chlorobutoxy)-4-[6-(4-chlorobutoxy)naphthalen-2-yl]-3,4-dihydro-1H-isoquinolin-2-yl]ethanone
• CAS: 133043-21-7
• 化学式: C₂₉H₃₃Cl₂NO₃
• 分子量: 514.492
• InChiKey: LZLLXKUUIINCMF-GDLZYMKVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.13
• 重原子数：
  35.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  38.77
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-acetyl-4,4-bis(4-hydroxy-3,5-dimethylphenyl)piperidine 、 (R)-(+)-2-acetyl-6-(4-chlorobutoxy)-4-<6-(4-chlorobutoxy)-2-naphthalenyl>-1,2,3,4-tetrahydroisoquinoline 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 120.0h， 以43%的产率得到(R)-(-)-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 、 cesium fluoride 、 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 251.0h， 生成 (R)-(+)-2-acetyl-6-(4-chlorobutoxy)-4-<6-(4-chlorobutoxy)-2-naphthalenyl>-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