optically inactive (E)-bis-(2-nitro-1-phenyl-ethyl)-diazene-N,N'-dioxide | 66618-68-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: optically inactive (E)-bis-(2-nitro-1-phenyl-ethyl)-diazene-N,N'-dioxide
• 英文别名: Opt.-inakt. (E)-Bis-(2-nitro-1-phenyl-aethyl)-diazen-N,N'-dioxid；dimeres (2-Nitro-1-nitroso-aethyl)-benzol
• CAS: 66618-68-6；215189-63-2
• 化学式: C₁₆H₁₆N₄O₆
• 分子量: 360.326
• InChiKey: SBSBJJSPVZBJHZ-FMQUCBEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  26.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  138.42
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  optically inactive (E)-bis-(2-nitro-1-phenyl-ethyl)-diazene-N,N'-dioxide 以 乙醇 为溶剂， 反应 1.0h， 以31%的产率得到2-硝基-1-苯基乙烷-1-酮肟
  参考文献：
  名称：

  Pseudonitrosites and Other Azodioxides with Vicinal Electron Acceptors

  摘要：

  Twelve vicinally substituted nitro-nitroso compounds (pseudonitrosites) were synthesized, nine of them for the first time. In the solid state the dimeric azodioxides are present. In the class of the pseudonitrosites 2a-h, all compounds exhibited comparatively strong antiplatelet activity in vitro (Born test: collagen). Four of them showed an IC50 below 10 mu M, 2a being the most active I substance with an IC50 = 2.1 mu M. When administered orally to rats (60 mg/kg) small antithrombotic effects were observed. The pseudonitrosite 6d was the most active compound(18% inhibition in arterioles). The in vitro decomposition of 2a at 37 degrees C gave NO and N2O, indicating that the above pharmacological effects were mediated by an NO-dependent mechanism. The replacement of the nitro group in the pseudonitrosite partial structure by other electron accepters i.e. acetyl, carboxyl, or acetyloxy groups leads to inactive (10a) or less active compounds (10b, c).

  DOI：

  10.1002/(sici)1521-4184(199803)331:3<111::aid-ardp111>3.0.co;2-z
• 作为产物：
  描述：

  苯乙烯 在 三氧化二氮 作用下， 以 甲苯 为溶剂， 以11%的产率得到optically inactive (E)-bis-(2-nitro-1-phenyl-ethyl)-diazene-N,N'-dioxide
  参考文献：
  名称：

  Pseudonitrosites and Other Azodioxides with Vicinal Electron Acceptors

  摘要：

  Twelve vicinally substituted nitro-nitroso compounds (pseudonitrosites) were synthesized, nine of them for the first time. In the solid state the dimeric azodioxides are present. In the class of the pseudonitrosites 2a-h, all compounds exhibited comparatively strong antiplatelet activity in vitro (Born test: collagen). Four of them showed an IC50 below 10 mu M, 2a being the most active I substance with an IC50 = 2.1 mu M. When administered orally to rats (60 mg/kg) small antithrombotic effects were observed. The pseudonitrosite 6d was the most active compound(18% inhibition in arterioles). The in vitro decomposition of 2a at 37 degrees C gave NO and N2O, indicating that the above pharmacological effects were mediated by an NO-dependent mechanism. The replacement of the nitro group in the pseudonitrosite partial structure by other electron accepters i.e. acetyl, carboxyl, or acetyloxy groups leads to inactive (10a) or less active compounds (10b, c).

  DOI：

  10.1002/(sici)1521-4184(199803)331:3<111::aid-ardp111>3.0.co;2-z

文献信息

• Action du monoxyde d'azote sur le phényléthylène et sur quelques arylalcènes
  作者：Jacques Tuaillon、Roger Perrot

  DOI：10.1002/hlca.19780610203

  日期：1978.3.8

  Nitric oxide reacts with phenylethylene and arylalkenes under the action of sunlight and at room temperature giving dimeric nitronitroso compounds prouved by IR. spectroscopy (see Table 2) and the corresponding nitroolefins. The main gaseous product is nitrogen as prouved by gaz liquid chromatography (see Table 1). The dimeric nitronitroso compounds can also be obtained by the reaction of dinitrogen

  一氧化氮在阳光的作用下和在室温下与苯基乙烯和芳基烯烃反应，生成二聚亚硝基亚硝基化合物，经红外光谱鉴定。光谱学（见表2）和相应的硝基烯烃。气相色谱法提供的主要气体产物是氮气（请参见表1）。二聚亚硝基亚硝基化合物也可以通过三氧化二氮与烯烃的反应获得。进一步讨论了亚硝基化合物的结构。可以将它们还原得到对应于硝基的单胺，也可以将其转化为硝基烯烃。