(1R,9S,13R,16S)-15-[(1R)-1-phenylethyl]-8,14-dioxa-15-azatetracyclo[7.6.1.02,7.013,16]hexadeca-2,4,6-triene | 182966-75-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (1R,9S,13R,16S)-15-[(1R)-1-phenylethyl]-8,14-dioxa-15-azatetracyclo[7.6.1.02,7.013,16]hexadeca-2,4,6-triene
• CAS: 182966-75-2
• 化学式: C₂₁H₂₃NO₂
• 分子量: 321.419
• InChiKey: HVQWZMNEIJDQGW-VRZSJZFSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,9S,13R,16S)-15-[(1R)-1-phenylethyl]-8,14-dioxa-15-azatetracyclo[7.6.1.02,7.013,16]hexadeca-2,4,6-triene 在 palladium on activated charcoal 氢气 、 溶剂黄146 作用下， 反应 6.0h， 以90%的产率得到(+)-(1R,4aS,9aR)-1,2,3,4,4a,9a-hexahydro-9H-xanthen-1-ol
  参考文献：
  名称：

  Relative and absolute stereocontrol in intramolecular nitrone cycloadditions to the cyclohexene ring

  摘要：

  The intramolecular reactivity of a nitrone derived from 2-(cyclohexen-3-yloxy)benzaldehyde has been investigated. By using (R)-alpha-phenylethylamine as chiral auxiliary, enantiomerically pure (9-amino-substituted) 1,2,3,4,4a,9a-hexahydro-9H-xanthen-1-ols were produced in satisfactory way. Copyright (C) 1996 Published by Elsevier Science Ltd

  DOI：

  10.1016/0040-4020(96)00676-x
• 作为产物：
  描述：

  2-(cyclohexen-3-yloxy)benzaldehyde 、 (R)-1-Phenylethylhydroxylamine 在 calcium chloride 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以24%的产率得到(1R,9S,13R,16S)-15-[(1R)-1-phenylethyl]-8,14-dioxa-15-azatetracyclo[7.6.1.02,7.013,16]hexadeca-2,4,6-triene
  参考文献：
  名称：

  Relative and absolute stereocontrol in intramolecular nitrone cycloadditions to the cyclohexene ring

  摘要：

  The intramolecular reactivity of a nitrone derived from 2-(cyclohexen-3-yloxy)benzaldehyde has been investigated. By using (R)-alpha-phenylethylamine as chiral auxiliary, enantiomerically pure (9-amino-substituted) 1,2,3,4,4a,9a-hexahydro-9H-xanthen-1-ols were produced in satisfactory way. Copyright (C) 1996 Published by Elsevier Science Ltd

  DOI：

  10.1016/0040-4020(96)00676-x

文献信息

• Arrighi; Broggini; Terraneo, Synthesis, 2001, # 3, p. 473 - 477
  作者：Arrighi、Broggini、Terraneo

  DOI：——

  日期：——
• Relative and absolute stereocontrol in intramolecular nitrone cycloadditions to the cyclohexene ring
  作者：Gianluigi Broggini、Franco Folcio、Nicola Sardone、Gaetano Zecchi

  DOI：10.1016/0040-4020(96)00676-x

  日期：1996.9

  The intramolecular reactivity of a nitrone derived from 2-(cyclohexen-3-yloxy)benzaldehyde has been investigated. By using (R)-alpha-phenylethylamine as chiral auxiliary, enantiomerically pure (9-amino-substituted) 1,2,3,4,4a,9a-hexahydro-9H-xanthen-1-ols were produced in satisfactory way. Copyright (C) 1996 Published by Elsevier Science Ltd