3-(1,4-Dioxen-2-yl)-inden-1-one | 155449-22-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚和异茚
• 英文名称: 3-(1,4-Dioxen-2-yl)-inden-1-one
• 英文别名: 3-(2,3-Dihydro-1,4-dioxin-5-yl)inden-1-one
• CAS: 155449-22-2
• 化学式: C₁₃H₁₀O₃
• 分子量: 214.221
• InChiKey: GTVNCOTTWIIPFH-UHFFFAOYSA-N

物化性质

• 沸点：
  314.5±42.0 °C(predicted)
• 密度：
  1.340±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(1,4-Dioxen-2-yl)-inden-1-one 在 N-溴代丁二酰亚胺(NBS) 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 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
• 作为产物：
  描述：

  2,2-二溴-1-茚酮 在 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 7.92h， 生成 3-(1,4-Dioxen-2-yl)-inden-1-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.