(2'S,4'R,5'S,10'S)-10'-methoxy-5,5-dimethylspiro[1,3-dioxane-2,3'-6,9-dioxapentacyclo[9.7.0.02,4.05,10.012,17]octadeca-1(11),12,14,16-tetraene]-18'-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (2'S,4'R,5'S,10'S)-10'-methoxy-5,5-dimethylspiro[1,3-dioxane-2,3'-6,9-dioxapentacyclo[9.7.0.02,4.05,10.012,17]octadeca-1(11),12,14,16-tetraene]-18'-one
• 化学式: C₂₂H₂₄O₆
• 分子量: 384.429
• InChiKey: BQBMYJMMUCVKEZ-JXOCDABTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  28
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2'S,4'R,5'S,10'S)-10'-methoxy-5,5-dimethylspiro[1,3-dioxane-2,3'-6,9-dioxapentacyclo[9.7.0.02,4.05,10.012,17]octadeca-1(11),12,14,16-tetraene]-18'-one 在 三氟乙酸 作用下， 以 氯仿 为溶剂， 反应 1.0h， 以90%的产率得到2-<(2,2-Dimethyl-3-hydroxypropyl)oxy>-4-<(2-hydroxyethyl)oxy>benzazulene-5,13-dione
  参考文献：
  名称：

  Diels-Alder Reactions of Cyclopropenone Ketals: A Concise Tropolone Annulation Applicable to Rubrolone C Ring Introduction

  摘要：

  A concise tropolone annulation applicable to rubrolone C ring introduction is detailed based on the room-temperature [4 + 2] cycloaddition reaction of the cyclopropenone ketal 10 with the oxygenated diene 9. Conversion of the sensitive [4 + 2] cycloadduct 11 to the norcaradiene 18, low temperature electrocyclic rearrangement to a cycloheptatrienone ketal, and tautomerization to 12 provided a fully oxygenated tropolone analogous to that found in rubrolone.

  DOI：

  10.1021/jo00091a040
• 作为产物：
  描述：

  2,2-二溴-1-茚酮 在 N-溴代丁二酰亚胺(NBS) 、 叔丁基锂 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 lithium chloride 作用下， 以 二氯甲烷 为溶剂， 反应 8.42h， 生成 (2'S,4'R,5'S,10'S)-10'-methoxy-5,5-dimethylspiro[1,3-dioxane-2,3'-6,9-dioxapentacyclo[9.7.0.02,4.05,10.012,17]octadeca-1(11),12,14,16-tetraene]-18'-one
  参考文献：
  名称：

  Diels-Alder Reactions of Cyclopropenone Ketals: A Concise Tropolone Annulation Applicable to Rubrolone C Ring Introduction

  摘要：

  A concise tropolone annulation applicable to rubrolone C ring introduction is detailed based on the room-temperature [4 + 2] cycloaddition reaction of the cyclopropenone ketal 10 with the oxygenated diene 9. Conversion of the sensitive [4 + 2] cycloadduct 11 to the norcaradiene 18, low temperature electrocyclic rearrangement to a cycloheptatrienone ketal, and tautomerization to 12 provided a fully oxygenated tropolone analogous to that found in rubrolone.

  DOI：

  10.1021/jo00091a040

文献信息

• Diels-Alder Reactions of Cyclopropenone Ketals: A Concise Tropolone Annulation Applicable to Rubrolone C Ring Introduction
  作者：Dale L. Boger、Yan Zhu

  DOI：10.1021/jo00091a040

  日期：1994.6

  A concise tropolone annulation applicable to rubrolone C ring introduction is detailed based on the room-temperature [4 + 2] cycloaddition reaction of the cyclopropenone ketal 10 with the oxygenated diene 9. Conversion of the sensitive [4 + 2] cycloadduct 11 to the norcaradiene 18, low temperature electrocyclic rearrangement to a cycloheptatrienone ketal, and tautomerization to 12 provided a fully oxygenated tropolone analogous to that found in rubrolone.