(E)-1,2-bis(1-nitro-1-methylethyl)diazene 1,2 oxide | 111167-57-8

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: (E)-1,2-bis(1-nitro-1-methylethyl)diazene 1,2 oxide
• 英文别名: (E)-2-nitropropan-2-yl-[2-nitropropan-2-yl(oxido)azaniumylidene]-oxidoazanium
• CAS: 111167-57-8；112401-19-1
• 化学式: C₆H₁₂N₄O₆
• 分子量: 236.184
• InChiKey: AZIBGNACRQNSRD-BQYQJAHWSA-N

物化性质

• 沸点：
  383.9±52.0 °C(Predicted)
• 密度：
  1.328±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  149
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-硝基-2-亚硝基丙烷 以 氘代氯仿 为溶剂， 生成 (E)-1,2-bis(1-nitro-1-methylethyl)diazene 1,2 oxide
  参考文献：
  名称：

  2-硝基-2-亚硝基丙烷及其二聚体的物理性质和结构

  摘要：

  摘要 在 2-nitro-2-nitrosopropane (Ia) 的溶液中，其二聚体 (E)-1,2-bis(1-nitro-1-methylethyl)-diazene 1,2-dioxide (IIa) 的数量不等，已通过 1 H NMR 和 IR 光谱检测到。通过前一种方法，平衡常数在苯中估计为 0.11 l mol -1 ，在 DMSO 中为 0.17 l mol -1 ，而 Ia 的 VIS 光谱给出不太精确的结果。IIa 的 E 构型来自红外光谱和晶体学 X 射线研究；尚未检测到第二个立体异构体 (IIIa) 的存在。根据偶极矩，Ia 的构象 ap 和 sc 几乎相等，而晶体中 IIa 的构象是 ap 。因此，静电排斥力优于 gauche 效应。

  DOI：

  10.1016/0022-2860(89)80180-2

文献信息

• Pseudonitroles and Their Dimeric Azodioxides
  作者：Klaus Rehse、Martin Herpel

  DOI：10.1002/(sici)1521-4184(199802)331:2<79::aid-ardp79>3.0.co;2-9

  日期：1998.2

  Thirteen geminally substituted nitro-nitroso compounds (pseudonitroles) have been synthesized, four of them for the first time. In the solid state the pseudonitroles are dimerized to azo-dioxides. This is proved by IR spectroscopy, with the dimeric N-O valence vibration being observed between 1293 and 1306 cm(-1). Only 1,3-diphenyl-2-nitro-2-nitrosopropane is monomeric even when solid. This is backed by its blue color and an IR band at 1574 cm(-1). When dissolved in chloroform these azodioxides dissociate completely to the blue monomers (lambda(max) similar to 650 nm). Eight pseudonitroles inhibited the aggregation of blood platelets half-maximally at concentrations below 10 mu M (Born test, collagen). When administered orally to rats (60 mg/kg) the thrombus formation in mesenteric arterioles and venules was inhibited up to 25 percent (k: 1-nitro-1-nitrosocyclohexane). When kept in aqueous media at 37 degrees C nitric oxide and its reduced form, i.e. nitrosohydrogen, are released. This suggests that the above biological effects arise from an NO dependent mechanism. The lack of influence on the blood pressure of spontaneously hypertensive rats, however, strongly suggests that an enzyme supported rather than a thermal formation of NO occurs in vivo.