1,2,4-三氯-3-碘-5,6-二甲氧基苯 | 244037-28-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 1,2,4-三氯-3-碘-5,6-二甲氧基苯
• 英文名称: 1,2,4-trichloro-3-iodo-5,6-dimethoxybenzene
• 英文别名: 1,2-dimethoxy-4-iodo-3,5,6-trichlorobenzene；3,5,6-trichloro-4-iodoveratrole
• CAS: 244037-28-3
• 化学式: C₈H₆Cl₃IO₂
• 分子量: 367.398
• InChiKey: UJSOOCFUQZCRAQ-UHFFFAOYSA-N

物化性质

• 沸点：
  366.2±42.0 °C(Predicted)
• 密度：
  1.880±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  14
• 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：

  1,2,4-三氯-3-碘-5,6-二甲氧基苯 在 硫酸 、 硝酸 、 铜 作用下， 以 二氯甲烷 为溶剂， 反应 180.0h， 生成 2,2',3,3',6,6'-hexachloro-5-nitro-1,1'-biphenyl
  参考文献：
  名称：

  2,2‘,3,3‘,6,6‘-Hexachlorobiphenyl Hydroxylation by Active Site Mutants of Cytochrome P450 2B1 and 2B11

  摘要：

  The structural basis of species differences in cytochrome P450 2B-mediated hydroxylation of 2,2',3,3',6,6'-hexachlorobiphenyl (236HCB) was evaluated by using 14 site-directed mutants of cytochrome P450 2B1 and three point mutants of 2B11 expressed in Escherichia coli, To facilitate metabolite identification, seven possible products, including three hydroxylated and four dihydroxylated hexachlorobiphenyls, were synthesized by direct functionalization of precursors and Ullmann and crossed Ullmann reactions, HPLC and GC/MS analysis and comparison with authentic standards revealed that 2B1 2B11, and all their mutants produced 4,5-dihydroxy-236HCB and 5-hydroxy-236HCB, while 2B11 L363V and 2B1 I114V mutants also catalyzed hydroxylation at the 4-position. The amount of products formed by 2B1 mutants I114V, F206L, L209A, T302S, V363A, V363L, V367A, I477A, I477L, G478S, I480A, and I480L was smaller than that of the wild type. I477V exhibited unaltered 236HCB metabolism, and I480V produced twice as much dihydroxy product as the wild type, For 2B11, substitution of Val-114 or Asp-290 with lie decreased the product yields. Replacement of Leu-363 with Val dramatically altered the profile of 236HCB metabolites. In addition to an increase in the overall level of hydroxylation, the mutant mainly catalyzed hydroxylation at the 4-position. Incubation of P450 2B1 with 5-hydroxy-236HCB produced 4,5-dihydroxy-236HCB, which indicates that 4,5-dihydroxy-236HCB may be formed by a direct hydroxylation of 5-hydroxy-236HCB. The findings from this study demonstrate the importance of residues 114, 206, 209, 302, 363, 367, 477, 478, and 480 in 2B1 and 114, 290, and 363 in 2B11 for 236HCB metabolism.

  DOI：

  10.1021/tx990030j
• 作为产物：
  描述：

  4-碘藜芦醚 在 盐酸 、 双氧水 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 12.0h， 以82%的产率得到1,2,4-三氯-3-碘-5,6-二甲氧基苯
  参考文献：
  名称：

  一种1,2-二甲氧基-4-碘苯-3,5,6-三氯代苯 的制备方法

  摘要：

  本发明公开了一种1,2‑二甲氧基‑4‑碘苯‑3,5,6‑三氯代苯的制备方法，以4‑碘‑1,2‑二甲氧基苯为原料、以低碳链脂肪酸为溶剂、以双氧水和盐酸或者氯气作为氯代为氯源进行氯代，反应完成后，用亚硫酸氢盐溶液破坏过量的游离氯，经过抽滤、热搅拌洗涤、抽滤和干燥得到纯度在97％以上的产品。TLC为单一斑点。HPLC含量大于97％。本发明的反应制备的1,2‑二甲氧基‑4‑碘苯‑3,5,6‑三氯代苯方法中，避免了柱层析，操作简单、收率和纯度高。

  公开号：

  CN105732333B

文献信息

• Synthesis of Sterically Hindered Polychlorinated Biphenyl Derivatives
  作者：H.-J. Lehmler、S. Joshi、S. Vyas、M. Duffel、S. Parkin

  DOI：10.1055/s-0030-1258454

  日期：2011.4

  A series of sterically hindered (methoxylated) polychlorinated biphenyl derivatives were synthesized using the Suzuki and the Ullmann coupling reactions. The Suzuki coupling with Pd(dba)2/2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (DPDB) gave better yields (65-98%) compared to the classic Ullmann coupling reaction (20-38%). Despite the reactive catalyst system, no significant coupling with aromatic

  使用 Suzuki 和 Ullmann 偶联反应合成了一系列空间位阻（甲氧基化）多氯联苯衍生物。与经典的 Ullmann 偶联反应 (20-38%) 相比，Suzuki 与 Pd(dba) 2 /2-二环己基膦基-2',6'-二甲氧基联苯 (DPDB) 的偶联产生更好的产率 (65-98%)。尽管有反应性催化剂体系，但没有观察到与芳族氯取代基的显着偶联。四种 PCB 衍生物的晶体结构分析显示固态二面角范围为 69.7° 至 81.0°，这表明这些高度邻位取代的 PCB 衍生物具有一定的构象灵活性。 联芳基 - 钯 - Suzuki 交叉耦合 - Ullmann 交叉耦合 - 二面角