((1R,2R,3S,4S)-7,7-Dichloro-3-hydroxymethyl-bicyclo[2.2.1]hept-5-en-2-yl)-methanol | 151561-13-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ((1R,2R,3S,4S)-7,7-Dichloro-3-hydroxymethyl-bicyclo[2.2.1]hept-5-en-2-yl)-methanol
• CAS: 151561-13-6
• 化学式: C₉H₁₂Cl₂O₂
• 分子量: 223.099
• InChiKey: XLUPKKBJWOTEEC-KVFPUHGPSA-N

物化性质

• 沸点：
  337.8±37.0 °C(predicted)
• 密度：
  1.44±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.19
• 重原子数：
  13.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  ((1R,2R,3S,4S)-7,7-Dichloro-3-hydroxymethyl-bicyclo[2.2.1]hept-5-en-2-yl)-methanol 在 sodium tetrahydroborate 、 cyanocobalamin 、 对甲苯磺酸 作用下， 以 甲醇 、 乙二醇二甲醚 、 苯 为溶剂， 反应 3.33h， 生成 4-((1S,2S,5S,8R,9R)-12-Chloro-4,6-dioxa-tricyclo[7.2.1.0^2,8]dodec-10-en-5-yl)-benzonitrile
  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：

  Acetic acid (1R,2R,3S,4S)-3-acetoxymethyl-7,7-diethoxy-bicyclo[2.2.1]hept-5-en-2-ylmethyl ester 在 氢氧化钾 、 五氯化磷 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 34.0h， 生成 ((1R,2R,3S,4S)-7,7-Dichloro-3-hydroxymethyl-bicyclo[2.2.1]hept-5-en-2-yl)-methanol
  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