(4-bromobutyl)dimethylphosphine oxide | 153495-60-4

• 物质功能分类: 有机原料 - 有机膦化合物
• 分子结构分类: 有机化合物 - 有机磷化合物 - 有机膦及其衍生物
• 英文名称: (4-bromobutyl)dimethylphosphine oxide
• 英文别名: 1-Bromo-4-dimethylphosphorylbutane
• CAS: 153495-60-4
• 化学式: C₆H₁₄BrOP
• 分子量: 213.054
• InChiKey: BZJAISOKBJYYSU-UHFFFAOYSA-N

物化性质

• 沸点：
  320.2±25.0 °C(Predicted)
• 密度：
  1.291±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (4-bromobutyl)dimethylphosphine oxide 在 sodium hydroxide 、 肼 作用下， 以 甲醇 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.58h， 生成 (4-isothiocyanatobutyl)dimethylphosphine oxide
  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：

  1,4-二溴丁烷 、 甲基氯化镁 在 二乙基亚磷酸氢酯 作用下， 生成 (4-bromobutyl)dimethylphosphine oxide
  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

• Cellular accumulation of phosphonate analogs of hiv protease inhibitor compounds
  申请人：Arimilli N. Murty

  公开号：US20070010489A1

  公开（公告）日：2007-01-11

  Phosphonate substituted compounds with HIV protease inhibitory properties having use as therapeutics and for other industrial purposes are disclosed. The compositions inhibit 5 HIV protease activity and/or are useful therapeutically for the treatment of AIDS and other antiviral infections, as well as in assays for the detection of HIV protease.

  本发明揭示了具有HIV蛋白酶抑制剂性质的膦酸酯取代化合物，其具有作为治疗剂和其他工业用途的用途。该组合物抑制5型HIV蛋白酶活性和/或在治疗艾滋病和其他抗病毒感染方面具有治疗作用，以及在检测HIV蛋白酶方面的检测中有用。
• 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：——
• US7649015B2
  申请人：——

  公开号：US7649015B2

  公开（公告）日：2010-01-19