1-硝基-3-(3-硝基苯氧基)苯 | 38490-83-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-硝基-3-(3-硝基苯氧基)苯
• 英文名称: 3,3'-dinitrodiphenyl ether
• 英文别名: bis-(3-nitro-phenyl)-ether；Bis-(3-nitro-phenyl)-aether；4,4'-bis(nitrophenyl) ether；Bis[m-nitrophenyl]ether；1-nitro-3-(3-nitrophenoxy)benzene
• CAS: 38490-83-4
• 化学式: C₁₂H₈N₂O₅
• 分子量: 260.206
• InChiKey: QYBOKWQLGVZMHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-硝基-3-(3-硝基苯氧基)苯 在 水 、 镍 作用下， 生成 bis-[3-(4-methyl-thiazol-2-ylamino)-phenyl]-ether
  参考文献：
  名称：

  Tomita; Takase, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1955, vol. 75, p. 1077,1079

  摘要：

  DOI：
• 作为产物：
  描述：

  间硝基苯酚 在 copper diacetate 、 4 A molecular sieve 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 1-硝基-3-(3-硝基苯氧基)苯
  参考文献：
  名称：

  Regioselective Conversion of Arylboronic Acids to Phenols and Subsequent Coupling to Symmetrical Diaryl Ethers

  摘要：

  DOI：

  10.1021/jo0015873

文献信息

• Mechanism of Replacement of the Nitro Group and Fluorine Atom in meta-Substituted Nitrobenzenes by Phenols in the Presence of Potassium Carbonate
  作者：I. A. Khalfina、V. M. Vlasov

  DOI：10.1007/s11178-005-0280-1

  日期：2005.7

  The relative mobilities of the nitro group and fluorine atom in 1,3-dinitrobenzene and 1-fluoro-3-nitrobenzene by the action of phenols in the presence of potassium carbonate in dimethylformamide at 95–125°C were studied by the competing reaction method. The rate constant ratios k(NO2)/k(F) were correlated with the differences between the corresponding activation parameters (ΔΔH ≠ and ΔΔ S ≠). The greater mobility of the nitro group was found to be determined by the entropy control of the reactivity of arenes. The activation parameters (ΔH ≠ and ΔS ≠) were calculated, and the enthalpy-entropy compensation effect was revealed. The reaction mechanism is discussed.

  采用竞争反应法研究了在二甲基甲酰胺中，于 95-125°C 下，在碳酸钾存在下，1,3-二硝基苯和 1-氟-3-硝基苯中的硝基和氟原子在苯酚作用下的相对迁移率。速率常数比 k(NO2)/k(F)与相应活化参数（ΔΔH≠和ΔΔS≠）之间的差异相关。研究发现，硝基的更大流动性是由羰基反应性的熵控制决定的。计算了活化参数（ΔH ≠ 和 ΔS ≠），并揭示了焓熵补偿效应。讨论了反应机理。
• Intramolecular exchange coupling of arylnitrenes by OXYGEN
  作者：Masaki Minato、Paul M. Lahti

  DOI：10.1002/poc.610070905

  日期：1994.9

  a high-spin open-shell dinitrene. The results are consistent with oxygen being a weak exchange coupling linker in pi-conjugated open-shell molecules. The observed ground-state spin multiplicities are in accord with qualitative superexchange and connectivity models, despite any perturbations due to resonance effects between the oxygen linker and p-nitrene sites.

  一系列的米，Ñ '-diazidodiphenyl醚（米≤N，M = 3,4; ñ = 3,4）在77K冷冻，玻璃状2-甲基四氢呋喃矩阵以生成相应的二苯基乙醚光分解米，Ñ ' -二苯甲醚，用于电子自旋共振（ESR）光谱研究。3,4'-二叠氮二苯醚的ESR谱图为nit D / hc ∣ = 0·972 cm -1的单氮化物峰，还表现出a D / hc ∣ = 0·162 cm-的弱二氮化物五重体光谱。 1个ESR光谱强度与温度的关系（居里定律）与高自旋基态或很小的单重态-五重态带隙一致。二（3-叠氮苯基）醚产生一个强的单氮化物峰，∣ D / hc ∣ = 0·996 cm -1和一个五重态二硝烯ESR光谱（∣ D / hc ∣ = 0·162 cm -1），表现出非线性居里定律强度行为与五重奏一致，该五重奏是在单重态基态上方40 cal mol -1的热填充激发态。二（4-叠氮基苯基）醚给出一个强的单硝烯峰，∣
• Ph-dependent nmda receptor antagonists
  申请人：——

  公开号：US20040138502A1

  公开（公告）日：2004-07-15

  NMDA receptor blockers, including pH-sensitive NMDA receptor blockers, are provided as neuroprotective drugs that are useful in stroke, traumatic brain injury, epilepsy, and other neurologic events that involve acidification of brain or spinal cord tissue. Compositions and methods of this invention are used for treating neurodegeneration resulting from NMDA receptor activation. The compounds described herein have enhanced activity in brain tissue having lower-than normal pH due to pathological conditions such as hypoxia resulting from stroke, traumatic brain injury, global ischemia tat may occur during cardiac surgery, hypoxia tat may occur following cessation of breathing, pre-eclampsia, spinal cord trauma, epilepsy, chronic pain, vascular dementia and glioma tumors. Compounds described herein are also useful in preventing neurodegeneration in patients with Parkinson's Alzheimer's, Huntington's chorea, ALS, and other neurodegenerative conditions known to the art to be responsive to treatment using NMDA receptor blockers. Preferably the compounds provided herein are allosteric NMDA inhibitors.

  NMDA受体阻滞剂，包括pH敏感的NMDA受体阻滞剂，被提供作为神经保护药物，可用于中风、创伤性脑损伤、癫痫和其他涉及大脑或脊髓组织酸化的神经事件。本发明的组合物和方法用于治疗由NMDA受体激活引起的神经退行性疾病。所述化合物在具有低于正常pH的脑组织中具有增强的活性，这是由于病理条件（如中风引起的低氧血症、创伤性脑损伤、在心脏手术期间可能发生的全局缺血、呼吸停止后可能发生的低氧血症、妊娠期高血压综合症、脊髓损伤、癫痫、慢性疼痛、血管性痴呆和胶质瘤等）。所述化合物也可用于预防帕金森病、阿尔茨海默病、亨廷顿舞蹈症、肌萎缩侧索硬化症和其他已知对使用NMDA受体阻滞剂治疗有反应的神经退行性疾病患者的神经退行性。优选地，本文提供的化合物是变构NMDA抑制剂。
• PH-dependent NMDA receptor antagonists
  申请人：Traynelis Stephen F.

  公开号：US20090023791A1

  公开（公告）日：2009-01-22

  NMDA receptor blockers, including pH-sensitive NMDA receptor blockers, are provided as neurprotective drugs that are useful in stroke, traumatic brain injury, epilepsy, and other neurologic events that involve acidification of brain or spinal cord tissue. Compositions and methods of this invention are used for treating neurodegeneration resulting from NMDA receptor activation. The compounds described herein have enhanced activity in brain tissue having lower than normal pH due to pathological conditions such as hypoxia resulting from stroke, traumatic brain injury, global ischemia that may occur during cardiac surgery, hypoxia that may occur following cessation of breathing, pre-eclampsia, spinal cord trauma, epilepsy, chrounic pain, vascular dementia and glioma rumors. Compounds described herein are also useful in preventing neurodegeneration in patients with Parkinson's Alzheimer's, Huntington's chorea, ALS, and other neurodegenerative conditions known to the art to be responsive to treatment using NMDA receptor blockers. Prefebably the compounds provided herein are allosteric NMDA inhibitors.

  NMDA受体阻滞剂，包括pH敏感的NMDA受体阻滞剂，作为神经保护药物提供，可用于中风、创伤性脑损伤、癫痫和其他涉及脑或脊髓组织酸化的神经事件。本发明的组合物和方法用于治疗由NMDA受体激活引起的神经退行性疾病。所述化合物在具有低于正常pH的脑组织中具有增强的活性，这是由于病理情况（如中风、创伤性脑损伤、可能发生于心脏手术期间的全球性缺血、呼吸停止后可能发生的低氧、先兆子痫、脊髓损伤、癫痫、慢性疼痛、血管性痴呆和胶质瘤）所致。所述化合物还可用于预防帕金森病、阿尔茨海默病、亨廷顿舞蹈症、肌萎缩侧索硬化症和其他已知对使用NMDA受体阻滞剂治疗有响应的神经退行性疾病患者的神经退行性。最好所提供的化合物是变构的NMDA抑制剂。
• Method of preparing 3,3'-dinitrodiphenyl ether
  申请人：MITSUI TOATSU CHEMICALS, Inc.

  公开号：EP0193358A1

  公开（公告）日：1986-09-03

  This invention is a method for preparing 3,3'-dinitrodiphenylether by use of m-dinitrobenzene as a raw material. Namely, 3,3'-dinitrodiphenylether is prepared by a condensation reaction of m-dinitrobenzene with m-nitrophenol in dipolar aprotic solvents in the presence of a base, or a self-condensation reaction of m-dinitrobenzene in the dipolar aprotic solvents in the presence of nitrite or in the presence of m-nitrophenol and the base.

  本发明是一种以间二硝基苯为原料制备 3,3'-二硝基二苯醚的方法。也就是说，3,3'-二硝基二苯醚是通过间二硝基苯与间硝基苯酚在二极性非丙烷溶剂中在碱存在下的缩合反应，或间二硝基苯在二极性非丙烷溶剂中在亚硝酸盐存在下或在间硝基苯酚和碱存在下的自缩合反应制备的。