3-cyanocyclohexyl methyl sulfide | 153495-68-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-cyanocyclohexyl methyl sulfide
• 英文别名: 3-Methylsulfanylcyclohexane-1-carbonitrile
• CAS: 153495-68-2
• 化学式: C₈H₁₃NS
• 分子量: 155.264
• InChiKey: RWSBDMUHKXTFKI-UHFFFAOYSA-N

物化性质

• 沸点：
  282.0±33.0 °C(predicted)
• 密度：
  1.02±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  49.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-cyanocyclohexyl methyl sulfide 在 sodium hydroxide 、 potassium sulfate 、 potassium hydrogensulfate 、 lithium aluminium tetrahydride 、 oxone 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 氯仿 、 水 为溶剂， 反应 27.5h， 生成 cis-(3-(methylsulfonyl)cyclohexyl)methyl isothiocyanate
  参考文献：
  名称：

  Design and synthesis of bifunctional isothiocyanate analogs of sulforaphane: correlation between structure and potency as inducers of anticarcinogenic detoxication enzymes

  摘要：

  Thirty-five bifunctional isothiocyanates were synthesized as structural analogs of sulforaphane [(-)-l-isothiocyanato-4(R)-(methylsulfinyl)butane] that was recently isolated from broccoli as the principal and very potent inducer of detoxication (phase 2) enzymes in mouse tissues and murine hepatoma cells (Hepa 1c1c7) in culture (Zhang, Y.; Talalay, P.; Cho, C.-G.; Posner, G. Il. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 2399-2403). Determination of the potency of each analog in inducing NAD(P)H:quinone reductase, a phase 2 detoxication enzyme, has allowed generalizations concerning the relation of structure and activity. The most potent analogs were bifunctional derivatives in which the isothiocyanate group was separated from a methylsulfonyl or an acetyl group by three or four carbon atoms, and in some of which these groups were conformationally restricted. Among these analogs, the bicyclic ketoisothiocyanate (+/-)-exo-2-acetyl-6-isothiocyanatonorbornane (30) was a very potent inducer (comparable to sulforaphane) of quinone reductase in hepatoma cells, and it also induced both quinone reductase and glutathione transferases in several mouse organs in vivo. This and related bicyclic ketoisothiocyanates represent potent phase 2 enzyme inducers that are relatively easily synthesized and that may be more stable metabolically than the natural sulfoxide sulforaphane.

  DOI：

  10.1021/jm00027a021
• 作为产物：
  描述：

  3-methylsulfanylcyclohexanone 以 甲醇 为溶剂， 反应 4.0h， 生成 3-cyanocyclohexyl methyl sulfide
  参考文献：
  名称：

  Design and synthesis of bifunctional isothiocyanate analogs of sulforaphane: correlation between structure and potency as inducers of anticarcinogenic detoxication enzymes

  摘要：

  Thirty-five bifunctional isothiocyanates were synthesized as structural analogs of sulforaphane [(-)-l-isothiocyanato-4(R)-(methylsulfinyl)butane] that was recently isolated from broccoli as the principal and very potent inducer of detoxication (phase 2) enzymes in mouse tissues and murine hepatoma cells (Hepa 1c1c7) in culture (Zhang, Y.; Talalay, P.; Cho, C.-G.; Posner, G. Il. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 2399-2403). Determination of the potency of each analog in inducing NAD(P)H:quinone reductase, a phase 2 detoxication enzyme, has allowed generalizations concerning the relation of structure and activity. The most potent analogs were bifunctional derivatives in which the isothiocyanate group was separated from a methylsulfonyl or an acetyl group by three or four carbon atoms, and in some of which these groups were conformationally restricted. Among these analogs, the bicyclic ketoisothiocyanate (+/-)-exo-2-acetyl-6-isothiocyanatonorbornane (30) was a very potent inducer (comparable to sulforaphane) of quinone reductase in hepatoma cells, and it also induced both quinone reductase and glutathione transferases in several mouse organs in vivo. This and related bicyclic ketoisothiocyanates represent potent phase 2 enzyme inducers that are relatively easily synthesized and that may be more stable metabolically than the natural sulfoxide sulforaphane.

  DOI：

  10.1021/jm00027a021

文献信息

• Posner Gary H., Cho Cheon-Gyu, Green Julianne V., Zhang Yuesheng, Talalay+, J. Med. Chem, 37 (1994) N 1, S 170-176
  作者：Posner Gary H., Cho Cheon-Gyu, Green Julianne V., Zhang Yuesheng, Talalay+

  DOI：——

  日期：——
• Design and synthesis of bifunctional isothiocyanate analogs of sulforaphane: correlation between structure and potency as inducers of anticarcinogenic detoxication enzymes
  作者：Gary H. Posner、C.-G. Cho、Julianne V. Green、Yuesheng Zhang、Paul Talalay

  DOI：10.1021/jm00027a021

  日期：1994.1

  Thirty-five bifunctional isothiocyanates were synthesized as structural analogs of sulforaphane [(-)-l-isothiocyanato-4(R)-(methylsulfinyl)butane] that was recently isolated from broccoli as the principal and very potent inducer of detoxication (phase 2) enzymes in mouse tissues and murine hepatoma cells (Hepa 1c1c7) in culture (Zhang, Y.; Talalay, P.; Cho, C.-G.; Posner, G. Il. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 2399-2403). Determination of the potency of each analog in inducing NAD(P)H:quinone reductase, a phase 2 detoxication enzyme, has allowed generalizations concerning the relation of structure and activity. The most potent analogs were bifunctional derivatives in which the isothiocyanate group was separated from a methylsulfonyl or an acetyl group by three or four carbon atoms, and in some of which these groups were conformationally restricted. Among these analogs, the bicyclic ketoisothiocyanate (+/-)-exo-2-acetyl-6-isothiocyanatonorbornane (30) was a very potent inducer (comparable to sulforaphane) of quinone reductase in hepatoma cells, and it also induced both quinone reductase and glutathione transferases in several mouse organs in vivo. This and related bicyclic ketoisothiocyanates represent potent phase 2 enzyme inducers that are relatively easily synthesized and that may be more stable metabolically than the natural sulfoxide sulforaphane.