4,10-dicarbomethoxy-trans,trans-2,6,8,12-dibenzohexacyclo<5.5.0.0^3,5.0^9,11>dodec-1(7)-ene | 136824-01-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 4,10-dicarbomethoxy-trans,trans-2,6,8,12-dibenzohexacyclo<5.5.0.0^3,5.0^9,11>dodec-1(7)-ene
• CAS: 136824-01-6
• 化学式: C₂₈H₂₄O₄
• 分子量: 424.496
• InChiKey: CYDPEUPRAOQJBB-ADPRKSCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.14
• 重原子数：
  32.0
• 可旋转键数：
  2.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4,10-dicarbomethoxy-trans,trans-2,6,8,12-dibenzohexacyclo<5.5.0.0^3,5.0^9,11>dodec-1(7)-ene 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以85%的产率得到anti-5,6,11,12,14,15,17,18-octahydro-13H,16H-5,12:6,11-di-endo-cyclopropatetracene-15,18-dimethanol
  参考文献：
  名称：

  含有锥状双键的新系统的合成：强保护锥状双键缺乏反应性

  摘要：

  DOI：

  10.1002/1522-2675(20010321)84:3<707::aid-hlca707>3.0.co;2-p
• 作为产物：
  描述：

  3,8-Dihydro-heptalene-3,8-dicarboxylic acid dimethyl ester 、 2-carboxybenzene diazonium chloride 在 methyloxirane 作用下， 以 various solvent(s) 为溶剂， 以40%的产率得到4,10-dicarbomethoxy-trans,trans-2,6,8,12-dibenzohexacyclo<5.5.0.0^3,5.0^9,11>dodec-1(7)-ene
  参考文献：
  名称：

  Syntheses of systems containing strained double bonds: cycloaddition reactions of trans-3,8-dicarbomethoxydihydroheptalene

  摘要：

  The two strained systems 5 and 6 are the objectives of synthetic and structural studies because of their relationship to syn- and anti-sesquinorbornenes. The Diels-Alder cycloaddition of maleic anhydride, p-benzoquinone, dimethylacetylene dicarboxylate, singlet oxygen, and benzyne to trans-3,8-dicarboxydihyroheptalene 7 have been investigated. It is shown that the second addition to this system goes only with dienophiles such as singlet oxygen and benzyne. Compound 15, a derivative of the anti compound 6, was synthesized and the structure investigated by X-ray diffraction. Although the molecule is strained, the central double bond exhibits a planar environment. The structure of compound 9, a precursor to a derivative of the syn compound 5, is reported. The double-bond environment at the ring juncture differs significantly from planarity, and the folding angle is 7.3-degrees.

  DOI：

  10.1021/jo00024a012