2-Bromo-3-(1,4-dioxen-2-yl)-1-indanone | 155449-21-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 2-Bromo-3-(1,4-dioxen-2-yl)-1-indanone
• 英文别名: 2-Bromo-3-(2,3-dihydro-1,4-dioxin-5-yl)-2,3-dihydroinden-1-one
• CAS: 155449-21-1
• 化学式: C₁₃H₁₁BrO₃
• 分子量: 295.133
• InChiKey: VIVDIEKPUNZLCT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  2-Bromo-3-(1,4-dioxen-2-yl)-1-indanone 在 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， 以72%的产率得到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
• 作为产物：
  描述：

  2,2-二溴-1-茚酮 在 叔丁基锂 、 三乙胺 、 lithium chloride 作用下， 以 二氯甲烷 为溶剂， 反应 7.42h， 生成 2-Bromo-3-(1,4-dioxen-2-yl)-1-indanone
  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.