5,6-bis(hydroxymethyl)-1,2,3,4-tetrachlorobicyclo<2.2.1>hept-2-ene | 91004-19-2

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: 5,6-bis(hydroxymethyl)-1,2,3,4-tetrachlorobicyclo<2.2.1>hept-2-ene
• 英文别名: 2.3-Dihydroxymethylen-1.4.5.6-tetrachlor-bicyclo<2.2.1>-hepten-5；2.3-Dihydroxymethylen-1.4.5.6-tetrachlor-bicyclo[2.2.1]-hepten-5；[1,4,5,6-Tetrachloro-3-(hydroxymethyl)-2-bicyclo[2.2.1]hept-5-enyl]methanol
• CAS: 91004-19-2
• 化学式: C₉H₁₀Cl₄O₂
• 分子量: 291.989
• InChiKey: GCXPHKUCBPHVEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  二乙氧基甲烷 、 5,6-bis(hydroxymethyl)-1,2,3,4-tetrachlorobicyclo<2.2.1>hept-2-ene 以6%的产率得到1,9,10,11-tetrachloro-2,3:8,7-endo-4,6-dioxatricyclo<7.2.1.0^2,8>dodec-10-ene
  参考文献：
  名称：

  Synthesis and structure-activity relationships of a series of insecticidal dioxatricyclododecenes acting as the noncompetitive antagonist of GABAA receptors

  摘要：

  Chlorinated analogues of 5-substituted 2,3:8,7-endo-4,6-dioxatricyclo[7.2.1.0(2,8)]dodec-10-ene (DTD) and 2,3:8,7-endo-4,6-dioxa-5-thiatricyclo[7.1.1.0(2,8)]dodec-10-ene 5-oxide were prepared. With -CH2-, -CH(Me)-, and -S(O)- at the 5 position, the presence of chlorine atoms in the norbornene moiety was important in exerting toxic effects to houseflies, while with -CH(n-Pr)- and -CH(Ph-CN-4)- the introduction of chlorine atoms resulted in a loss of toxic activity. The effect of the presence of chlorine atoms on the potency in inhibiting [S-35]tert-butylbicyclophosphorothionate (TBPS) binding to rat brain membranes was found to be correlated to their insecticidal activity. A good correlation (r=0.807) was obtained between insecticidal activity and the potency in inhibiting [S-35]TBPS binding for 29 compounds, including known noncompetitive antagonists of GABA(A) receptors. The Scatchard analysis indicated that both types of analogues, 1,9,10,11,12,12-hexachloro-DTD and 5-(4-cyanophenyl)-DTD, act competitively at the TBPS binding site in the GABA-gated chloride channel. These two types of analogues, however, appear to interact with slightly different subsites within the TBPS binding site.

  DOI：

  10.1021/jf00035a059
• 作为产物：
  描述：

  顺式-1,2-二羟甲基乙烯 、 1,2,3,4-四氯-1,3-环戊二烯 以 1,4-二氧六环 为溶剂， 反应 15.0h， 以11%的产率得到5,6-bis(hydroxymethyl)-1,2,3,4-tetrachlorobicyclo<2.2.1>hept-2-ene
  参考文献：
  名称：

  Synthesis and structure-activity relationships of a series of insecticidal dioxatricyclododecenes acting as the noncompetitive antagonist of GABAA receptors

  摘要：

  Chlorinated analogues of 5-substituted 2,3:8,7-endo-4,6-dioxatricyclo[7.2.1.0(2,8)]dodec-10-ene (DTD) and 2,3:8,7-endo-4,6-dioxa-5-thiatricyclo[7.1.1.0(2,8)]dodec-10-ene 5-oxide were prepared. With -CH2-, -CH(Me)-, and -S(O)- at the 5 position, the presence of chlorine atoms in the norbornene moiety was important in exerting toxic effects to houseflies, while with -CH(n-Pr)- and -CH(Ph-CN-4)- the introduction of chlorine atoms resulted in a loss of toxic activity. The effect of the presence of chlorine atoms on the potency in inhibiting [S-35]tert-butylbicyclophosphorothionate (TBPS) binding to rat brain membranes was found to be correlated to their insecticidal activity. A good correlation (r=0.807) was obtained between insecticidal activity and the potency in inhibiting [S-35]TBPS binding for 29 compounds, including known noncompetitive antagonists of GABA(A) receptors. The Scatchard analysis indicated that both types of analogues, 1,9,10,11,12,12-hexachloro-DTD and 5-(4-cyanophenyl)-DTD, act competitively at the TBPS binding site in the GABA-gated chloride channel. These two types of analogues, however, appear to interact with slightly different subsites within the TBPS binding site.

  DOI：

  10.1021/jf00035a059