1,5-bis-(2-<2-<1-(tert-butoxycarbonyl)methoxy>ethoxy>ethoxy)naphthalene | 223463-91-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,5-bis-(2-<2-<1-(tert-butoxycarbonyl)methoxy>ethoxy>ethoxy)naphthalene
• 英文别名: Tert-butyl 2-[2-[2-[5-[2-[2-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethoxy]ethoxy]ethoxy]naphthalen-1-yl]oxyethoxy]ethoxy]acetate
• CAS: 223463-91-0
• 化学式: C₃₀H₄₄O₁₀
• 分子量: 564.673
• InChiKey: DXHKFSRSIDLDHW-UHFFFAOYSA-N

物化性质

• 沸点：
  632.088±55.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.127±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  40
• 可旋转键数：
  22
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1,5-bis-(2-<2-<1-(tert-butoxycarbonyl)methoxy>ethoxy>ethoxy)naphthalene 在 吡啶 、 草酰氯 、 N,N-二甲基甲酰胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 86.0h， 生成 1,5-bis<2-(2-<1-<(1R,2S,5R)-menthoxycarbonyl>methoxy>ethoxy)ethoxy>naphthalene
  参考文献：
  名称：

  Molecular Meccano, 48Probing Co-Conformational Changes in Chiral [2]Rotaxanes by1H-NMR Spectroscopy

  摘要：

  The template-directed syntheses of three [2]rotaxanes possessing either chiral centers or elements of planar chirality, in one of their two mechanically interlocked components, have been realized and their solid-state structures have been analyzed by X-ray crystallography. In one instance, an enantiomerically pure dumbbell-shaped component incorporating a 1,5-dioxynaphthalene recognition site and two (1R,2S,5R)-menthyl stoppers was employed to template the formation of the achiral tetracationic cyclophane, cyclobis(paraquat-p-phenylene). The resulting enantiomerically pure [2]rotaxane was isolated in a yield of 55%. In the other two instances, an achiral 1,5-dioxynaphthalene-based dumbbell-shaped component was employed to template the formation of bipyridinium-based cyclophanes possessing either one or two elements of planar chirality. The resulting [2]rotaxane, possessing one element of planar chirality, was isolated as a racemate in a yield of 24%. The related [2]rotaxane, possessing two elements of planar chirality, was isolated as a mixture of a meso form and an enantiomeric pair in an overall yield of 28%. The H-1-NMR-spectroscopic analysis of this mixture revealed a diastereoisomeric ratio of 4:1. A degenerate co-conformational change was identified by variable-temperature H-1-NMR spectroscopy in all [2]rotaxanes. The symmetry loss arising from the introduction of one or two elements of planar chirality enabled the elucidation of the mechanism of this dynamic process in two instances.

  DOI：

  10.1002/(sici)1099-0690(199904)1999:4<899::aid-ejoc899>3.0.co;2-c
• 作为产物：
  描述：

  溴乙酸叔丁酯 、 1,5-bis[2-(2-hydroxyethoxy)ethoxy]naphthalene 在 sodium hydroxide 、 四丁基碘化铵 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 168.0h， 以25%的产率得到1,5-bis-(2-<2-<1-(tert-butoxycarbonyl)methoxy>ethoxy>ethoxy)naphthalene
  参考文献：
  名称：

  Molecular Meccano, 48Probing Co-Conformational Changes in Chiral [2]Rotaxanes by1H-NMR Spectroscopy

  摘要：

  The template-directed syntheses of three [2]rotaxanes possessing either chiral centers or elements of planar chirality, in one of their two mechanically interlocked components, have been realized and their solid-state structures have been analyzed by X-ray crystallography. In one instance, an enantiomerically pure dumbbell-shaped component incorporating a 1,5-dioxynaphthalene recognition site and two (1R,2S,5R)-menthyl stoppers was employed to template the formation of the achiral tetracationic cyclophane, cyclobis(paraquat-p-phenylene). The resulting enantiomerically pure [2]rotaxane was isolated in a yield of 55%. In the other two instances, an achiral 1,5-dioxynaphthalene-based dumbbell-shaped component was employed to template the formation of bipyridinium-based cyclophanes possessing either one or two elements of planar chirality. The resulting [2]rotaxane, possessing one element of planar chirality, was isolated as a racemate in a yield of 24%. The related [2]rotaxane, possessing two elements of planar chirality, was isolated as a mixture of a meso form and an enantiomeric pair in an overall yield of 28%. The H-1-NMR-spectroscopic analysis of this mixture revealed a diastereoisomeric ratio of 4:1. A degenerate co-conformational change was identified by variable-temperature H-1-NMR spectroscopy in all [2]rotaxanes. The symmetry loss arising from the introduction of one or two elements of planar chirality enabled the elucidation of the mechanism of this dynamic process in two instances.

  DOI：

  10.1002/(sici)1099-0690(199904)1999:4<899::aid-ejoc899>3.0.co;2-c

文献信息

• Molecular Meccano, 48Probing Co-Conformational Changes in Chiral [2]Rotaxanes by1H-NMR Spectroscopy
  作者：Peter R. Ashton、José A. Bravo、Françisco M. Raymo、J. Fraser Stoddart、Andrew J. P. White、David J. Williams

  DOI：10.1002/(sici)1099-0690(199904)1999:4<899::aid-ejoc899>3.0.co;2-c

  日期：1999.4

  The template-directed syntheses of three [2]rotaxanes possessing either chiral centers or elements of planar chirality, in one of their two mechanically interlocked components, have been realized and their solid-state structures have been analyzed by X-ray crystallography. In one instance, an enantiomerically pure dumbbell-shaped component incorporating a 1,5-dioxynaphthalene recognition site and two (1R,2S,5R)-menthyl stoppers was employed to template the formation of the achiral tetracationic cyclophane, cyclobis(paraquat-p-phenylene). The resulting enantiomerically pure [2]rotaxane was isolated in a yield of 55%. In the other two instances, an achiral 1,5-dioxynaphthalene-based dumbbell-shaped component was employed to template the formation of bipyridinium-based cyclophanes possessing either one or two elements of planar chirality. The resulting [2]rotaxane, possessing one element of planar chirality, was isolated as a racemate in a yield of 24%. The related [2]rotaxane, possessing two elements of planar chirality, was isolated as a mixture of a meso form and an enantiomeric pair in an overall yield of 28%. The H-1-NMR-spectroscopic analysis of this mixture revealed a diastereoisomeric ratio of 4:1. A degenerate co-conformational change was identified by variable-temperature H-1-NMR spectroscopy in all [2]rotaxanes. The symmetry loss arising from the introduction of one or two elements of planar chirality enabled the elucidation of the mechanism of this dynamic process in two instances.