3,4,5,6-tetrachloro-14-hydroxytetracyclo[6.4.1.(9,12).0(2,7)]tetradeca-3,5,10-triene-13-one | 1169513-43-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4,5,6-tetrachloro-14-hydroxytetracyclo[6.4.1.(9,12).0(2,7)]tetradeca-3,5,10-triene-13-one
• CAS: 1169513-43-2
• 化学式: C₁₄H₁₀Cl₄O₂
• 分子量: 352.044
• InChiKey: XZBPJDSFTXKLKC-ILAUZBBASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3,4,5,6-tetrachloro-14-hydroxytetracyclo[6.4.1.(9,12).0(2,7)]tetradeca-3,5,10-triene-13-one 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以75%的产率得到3,4,5,6-tetrachlorotetracyclo[6.4.1.1(9,12).0(2,7)]tetradeca-3,5,10-triene-13,14-dione
  参考文献：
  名称：

  From the anti-tricyclo[4.2.1.12,5]deca-3,7-diene framework to 4,5,6,7-tetrachloro-isoindenone derivatives

  摘要：

  Two formal trapping products of 4,5,6,7-tetrachloro-isoindenone (1b) can be obtained from the polycyclic precursor (4) in a multi-step sequence, thus guaranteeing the anti-orientation of the arene and alkene/arene units. Compound 2b was synthesized without the in situ generation of 4,5,6,7-tetrachloro-isoindenone 1b or cyclopentadiene and has been fully characterized. Furthermore, progress toward dibenzo derivative 3b, the poorly soluble [4+4] dimer of 1b, was made along analogous synthetic steps. In addition, the structures of two crucial intermediates were determined by X-ray crystallography. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.09.045
• 作为产物：
  描述：

  2,3,4,5-四氯噻吩 1,1-二氧化物 、 anti^9,10-10endo-hydroxytricyclo<4.2.1.1^2,5>deca-3,7-dien-9-one 在 碳酸氢钠 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以81%的产率得到3,4,5,6-tetrachloro-14-hydroxytetracyclo[6.4.1.(9,12).0(2,7)]tetradeca-3,5,10-triene-13-one
  参考文献：
  名称：

  Diels–Alder reactivity of anti-tricyclo[4.2.1.12,5]deca-3,7-diene derivatives

  摘要：

  The limited thermal stability of the polycyclic dione 1 can be circumvented by reacting its derivatives, hydroxyketone 3 and diol 4 with tetrachlorothiophene dioxide (6d) to yield the mono-Diels-Alder adduct 8 and rearranged polycyclic ether 11, respectively. The structures of both new products were confirmed by X-ray Structure determination. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.03.215