2,3,3a,9a-tetrahydro-1H-cyclopenta[b]chromen-9-one | 244084-54-6

• 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: 2,3,3a,9a-tetrahydro-1H-cyclopenta[b]chromen-9-one
• CAS: 244084-54-6
• 化学式: C₁₂H₁₂O₂
• 分子量: 188.226
• InChiKey: RVVNMFILTLMWGA-UHFFFAOYSA-N

物化性质

• 沸点：
  324.1±22.0 °C(Predicted)
• 密度：
  1.190±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3,3a,9a-tetrahydro-1H-cyclopenta[b]chromen-9-one 在 正丁基锂 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 正己烷 为溶剂， 反应 2.5h， 生成 9-(1,3-Dithian-2-yl)-9a-methyl-1,2,3,3a-tetrahydrocyclopenta[b]chromen-9-ol
  参考文献：
  名称：

  A New Redundant Rearrangement of Aromatic Ring Fused Cyclic α-Hydroxydithiane Derivatives. Synthesis of Aromatic Ring Fused Cyclic 1,2-Diketones with One-Carbon Ring Expansion

  摘要：

  A new reaction involving rearrangement of aromatic ring fused cyclic dithiane alcohol by N-chlorosuccinimide in CH2Cl2-H2O to the corresponding one-carbon ring expanded 1,2-diketone has been developed. A wide range of structurally varied dithiane alcohols have been found to undergo this rearrangement in high yields. The general criteria and reaction mechanism for this rearrangement have also been worked out.

  DOI：

  10.1021/jo990634s
• 作为产物：
  描述：

  1-环戊烯羧酸 、 苯酚 在 PPA 作用下， 反应 4.5h， 以30%的产率得到2,3,3a,9a-tetrahydro-1H-cyclopenta[b]chromen-9-one
  参考文献：
  名称：

  A New Redundant Rearrangement of Aromatic Ring Fused Cyclic α-Hydroxydithiane Derivatives. Synthesis of Aromatic Ring Fused Cyclic 1,2-Diketones with One-Carbon Ring Expansion

  摘要：

  A new reaction involving rearrangement of aromatic ring fused cyclic dithiane alcohol by N-chlorosuccinimide in CH2Cl2-H2O to the corresponding one-carbon ring expanded 1,2-diketone has been developed. A wide range of structurally varied dithiane alcohols have been found to undergo this rearrangement in high yields. The general criteria and reaction mechanism for this rearrangement have also been worked out.

  DOI：

  10.1021/jo990634s

文献信息

• A New Redundant Rearrangement of Aromatic Ring Fused Cyclic α-Hydroxydithiane Derivatives. Synthesis of Aromatic Ring Fused Cyclic 1,2-Diketones with One-Carbon Ring Expansion
  作者：Brindaban C. Ranu、Umasish Jana

  DOI：10.1021/jo990634s

  日期：1999.8.1

  A new reaction involving rearrangement of aromatic ring fused cyclic dithiane alcohol by N-chlorosuccinimide in CH2Cl2-H2O to the corresponding one-carbon ring expanded 1,2-diketone has been developed. A wide range of structurally varied dithiane alcohols have been found to undergo this rearrangement in high yields. The general criteria and reaction mechanism for this rearrangement have also been worked out.