(S)-1-<2-(6-methoxy-2-naphthyl)propionyl>piperidine | 123675-42-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-1-<2-(6-methoxy-2-naphthyl)propionyl>piperidine
• 英文别名: (2S)-2-(6-methoxynaphthalen-2-yl)-1-piperidin-1-ylpropan-1-one
• CAS: 123675-42-3
• 化学式: C₁₉H₂₃NO₂
• 分子量: 297.397
• InChiKey: FHTGZZVEXQYHHU-AWEZNQCLSA-N

物化性质

• 沸点：
  487.4±28.0 °C(Predicted)
• 密度：
  1.122±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-[[22,22-diethyl-17,28,45,48-tetramethyl-3-[2-(triethylazaniumyl)ethoxy]-10,15,30,35-tetraoxa-22-azoniaoctacyclo[34.6.2.26,9.216,19.226,29.02,7.020,25.039,43]pentaconta-1(42),2,4,6,8,16(48),17,19(47),26,28,36(44),37,39(43),40,45,49-hexadecaen-42-yl]oxy]ethyl-triethylazanium;trichloride 、 (S)-1-<2-(6-methoxy-2-naphthyl)propionyl>piperidine 生成 2-[[22,22-diethyl-17,28,45,48-tetramethyl-3-[2-(triethylazaniumyl)ethoxy]-10,15,30,35-tetraoxa-22-azoniaoctacyclo[34.6.2.26,9.216,19.226,29.02,7.020,25.039,43]pentaconta-1(42),2,4,6,8,16(48),17,19(47),26,28,36(44),37,39(43),40,45,49-hexadecaen-42-yl]oxy]ethyl-triethylazanium;(2S)-2-(6-methoxynaphthalen-2-yl)-1-piperidin-1-ylpropan-1-one;trichloride
  参考文献：
  名称：

  CASTO, PETER P.;GEORGIADIS, TAXIARCHIS M.;DIEDERICH, FRANCOIS, J. ORG. CHEM., 54,(1989) N5, C. 5835-5838

  摘要：

  DOI：
• 作为产物：
  描述：

  萘普生 在 吡啶 、 氯化亚砜 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 24.5h， 生成 (S)-1-<2-(6-methoxy-2-naphthyl)propionyl>piperidine
  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.
• CASTO, PETER P.;GEORGIADIS, TAXIARCHIS M.;DIEDERICH, FRANCOIS, J. ORG. CHEM., 54,(1989) N5, C. 5835-5838
  作者：CASTO, PETER P.、GEORGIADIS, TAXIARCHIS M.、DIEDERICH, FRANCOIS

  DOI：——

  日期：——