1,3,5-三溴-2,4-二甲氧基苯 | 25676-73-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 1,3,5-三溴-2,4-二甲氧基苯
• 英文名称: 2,4,6-Tribrom-resorcin-dimethylether
• 英文别名: 1,3,5-tribromo-2,4-dimethoxybenzene；2,4,6-tribromo-1,3-dimethoxybenzene
• CAS: 25676-73-7
• 化学式: C₈H₇Br₃O₂
• 分子量: 374.854
• InChiKey: AZFRKBCSVYYWDW-UHFFFAOYSA-N

物化性质

• 熔点：
  69-70 °C(Solv: ethanol (64-17-5))
• 沸点：
  338.0±37.0 °C(Predicted)
• 密度：
  2.015±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,3,5-三溴-2,4-二甲氧基苯 在 氢溴酸 、 溶剂黄146 作用下， 生成 2,4,6-三溴间苯二酚
  参考文献：
  名称：

  Kohn; Loeff, Monatshefte fur Chemie, 1924, vol. 45, p. 592

  摘要：

  DOI：
• 作为产物：
  描述：

  间苯二甲醚 在 溴 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以98%的产率得到1,3,5-三溴-2,4-二甲氧基苯
  参考文献：
  名称：

  Synthesis and Antiproliferative Activity of Natural and Non-Natural Polymethoxychalcones and Polymethoxyflavones

  摘要：

  合成了两个系列的五甲氧基查尔酮和五甲氧基黄酮类化合物，包括天然产物2′-羟基-3,4,5,4′,6′-五甲氧基查尔酮（8c）、5,6,7,8,3′,4′,5′-七甲氧基黄酮（6）、5,7,3′,4′,5′-五甲氧基黄酮（9c）、3-羟基-5,6,7,8,3′,4′,5′-七甲氧基黄酮（7）和3-羟基-5,7,3′,4′,5′-五甲氧基黄酮（10）。通过细胞计数试剂盒-8（CCK-8）测定法评估了这些化合物对三株人癌细胞系（HeLa、HCC1954和SK-OV-3）的体外抗增殖活性。结果显示，大多数合成化合物表现出中等到强效的抗增殖活性。一些化合物的潜能与阳性对照药物顺铂相当或更高。特别是化合物4c、4e、8a和9a的IC50值等于或低于10 μM，值得进一步研究。

  DOI：

  10.1007/s10600-019-02605-x

文献信息

• Toxic Metronidazole-Induced MRI Changes
  作者：Cheryl K Horlen、Charles F Seifert、Cathy S Malouf

  DOI：10.1345/aph.10028

  日期：2000.11

  To report a case of changes documented by magnetic resonance imaging (MRI) of the head probably due to accumulation of metronidazole in a patient with liver dysfunction.

  A 34-year-old Hispanic man with cirrhosis and hepatitis C being treated with metronidazole for Bacteroides fragilis meningitis and bacteremia developed ataxia, disorientation, and peripheral neuropathy. An MRI at the time meningitis was diagnosed was negative. After the patient received >60 g of metronidazole, an MRI revealed increased signal intensity below, behind, and lateral to the fourth ventricle. Concomitant metronidazole serum concentration was toxic at 35.1 μg/mL.

  This is the second reported case of metronidazole-induced MRI changes. Metronidazole is known to accumulate in patients with liver dysfunction and can cause peripheral neuropathy and central nervous system (CNS) dysfunction; these effects may take up to two years to completely resolve.

  Metronidazole dosages should be reduced in patients with liver dysfunction to prevent the accumulation of metronidazole, which can lead to CNS dysfunction and peripheral neuropathy.

  报告一例头部磁共振成像（MRI）显示的变化，可能是由于肝功能障碍患者体内甲硝唑积累所致。

  一名34岁的西班牙裔男子患有肝硬化和丙型肝炎，因拜杆菌脑膜炎和菌血症接受甲硝唑治疗，出现共济失调、定向障碍和周围神经病变。脑膜炎确诊时进行的MRI检查结果为阴性。患者接受了超过60克的甲硝唑后，MRI显示第四脑室下方、后方和侧面信号强度增加。同时，甲硝唑血清浓度达到35.1μg/mL，毒性较大。

  这是第二例报告的甲硝唑诱导的MRI变化。甲硝唑已知会在肝功能障碍患者体内积累，并可导致周围神经病变和中枢神经系统（CNS）功能障碍；这些影响可能需要长达两年的时间才能完全消除。

  应该在肝功能障碍患者中减少甲硝唑剂量，以防止甲硝唑积累，从而导致CNS功能障碍和周围神经病变。

• Kiehlmann, E.; Lauener, R. W., Canadian Journal of Chemistry, 1989, vol. 67, p. 335 - 344
  作者：Kiehlmann, E.、Lauener, R. W.

  DOI：——

  日期：——
• Natoli, Maria C.; Agozzino, Pasquale; Ceraulo, Leopoldo, Gazzetta Chimica Italiana, 1983, vol. 113, # 7/8, p. 493 - 502
  作者：Natoli, Maria C.、Agozzino, Pasquale、Ceraulo, Leopoldo、Lamartina, Liliana

  DOI：——

  日期：——
• Antiferromagnetic Exchange Interaction among the Three Spins Placed in an Isosceles Triangular Configuration in 2,4-Dimethoxy-1,3,5-benzenetriyltris(<i>N</i>-<i>tert</i>-butyl nitroxide)
  作者：Junpei Fujita、Masakazu Tanaka、Hiroshi Suemune、Noboru Koga、Kenji Matsuda、Hiizu Iwamura

  DOI：10.1021/ja961849b

  日期：1996.1.1

  2,4-Dimethoxy-1,3,5-benzenetriyltris(N-tert-butyl nitroxide) (3) was prepared by lithiation of 2,4-dimethoxy-1,3,5-tribromobenzene followed by the reaction with 2-methyl-2-nitrosopropane and subsequent oxidation with Ag2O. The triradical crystallizes in the orthorhombic space group Pnma (no. 62) with four molecules in the unit cell of dimensions a = 18.200(3) Angstrom, b = 19.018(3) Angstrom, and c = 6.659(5) Angstrom. X-ray analysis for an orange plate single crystal of 3 revealed that the three nitroxide radicals in a molecule have large dihedral angles (90 degrees and 79 degrees) between N-O bonds and the benzene ring plane in the all-syn conformation and the distances between them are 5.44 and 5.28 Angstrom. An EPR spectrum of triradical 3 in frozen toluene solution showed quartet signals (g = 2.0062, \D/hc\ = 0.010, and \E/hc\ = 0.0004 cm(-1)) in addition to the signals at g = 4.019 and 6.035 due to Delta m(s) = 2 and 3 transitions, respectively. Temperature dependence of molar susceptibility for a microcrystalline sample obtained by SQUID measurements suggested that the antiferromagnetic interaction produces a doublet ground state in triradical 3. Experimental data were fitted in terms of the equation derived from an isosceles triangular three spin system (H = -2J(SA1SB + SBSA2 + alpha SA1SA2) with negative J's to afford two sets of the best fitting parameters: J/k(B) = -41.5 K, alpha = 0.31 and J/k(B) = -22.3 K, alpha = 2.29. The former J/k(B) value is more consistent with J/k(B) = -39.7 K for the reference biradical, 1-bromo-2,4-dimethoxy-3,5-benzenediylbis(N-tert-butyl nitroxide) (4). In triradical 3, therefore, the ground spin state would be a doublet with the stronger antiferromagnetic interaction between the spins at 1 and 3 positions and 3 and 5 positions polarizing the ferromagnetic alignment of the 1 and 5 spins, providing the first demonstration of an organic triradical showing competing interactions.
• KIEHLMANN, E.;LAUENER, R. W., CAN. J. CHEM., 67,(1989) N, C. 335-344
  作者：KIEHLMANN, E.、LAUENER, R. W.

  DOI：——

  日期：——