4-bromo-5-chloropyrocatechol | 369354-51-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-bromo-5-chloropyrocatechol
• 英文别名: 4-bromo-5-chloro-pyrocatechol；5-Chlor-4-brom-1.2-dihydroxy-benzol；4-Brom-5-chlor-brenzcatechin；4-Bromo-5-chlorobenzene-1,2-diol；4-bromo-5-chlorobenzene-1,2-diol
• CAS: 369354-51-8
• 化学式: C₆H₄BrClO₂
• 分子量: 223.454
• InChiKey: RNNZLGSNEGYSIR-UHFFFAOYSA-N

物化性质

• 沸点：
  319.0±37.0 °C(Predicted)
• 密度：
  1.952±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-bromo-5-chloropyrocatechol 在 五氯化磷 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 8.0h， 生成 2,6,7-trichloro-2-oxo-4-phenylbenzo[e]-1,2λ⁵-oxaphosphorin-3-ene
  参考文献：
  名称：

  摘要：

  According to the NMR, IR, and high-resolution mass spectra, the major products of the reactions of 5,6-dibromo-2-chlorobenzo[d]-1,3,2-dioxaphosphole 2,2-dichloride with arylacetylenes are 4-aryl-6,7-dibromo-2-chloro-5,6-benzo[e]-1,2-oxaphosphorin-3-ene 2-oxides. The steric structure of one of the hydrolysis products, 2-hydroxy-6,7-dibromo-4-phenyl-5,6-benzo[e]-1,2-oxaphosphorin-3-ene 2-oxide, was studied by single crystal X-ray diffraction.

  DOI：

  10.1023/a:1012381423101
• 作为产物：
  描述：

  4-氯邻苯二酚 在 溴 、 溶剂黄146 作用下， 生成 4-bromo-5-chloropyrocatechol
  参考文献：
  名称：

  Expeditious Synthesis of Vialinin B, an Extremely Potent Inhibitor of TNF-α Production

  摘要：

  A first total synthesis of vialinin B, a powerful inhibitor (IC50 20 pM) of TNF-alpha production, is described. The key reactions include a double Suzuki-Miyaura coupling of electron-rich aryl bromide with a couple of phenylboronic acids, a Cu-mediated Ullmann reaction, and a LHMDS-promoted phenylacetylation. This synthesis proceeded in 11 steps with 18% overall yield from a known sesamol derivative.

  DOI：

  10.1021/ol9020833

文献信息

• Slooff, Recueil des Travaux Chimiques des Pays-Bas, 1935, vol. 54, p. 995,999
  作者：Slooff

  DOI：——

  日期：——
• Expeditious Synthesis of Vialinin B, an Extremely Potent Inhibitor of TNF-α Production
  作者：Yue Qi Ye、Hiroyuki Koshino、Jun-ichi Onose、Kunie Yoshikawa、Naoki Abe、Shunya Takahashi

  DOI：10.1021/ol9020833

  日期：2009.11.5

  A first total synthesis of vialinin B, a powerful inhibitor (IC50 20 pM) of TNF-alpha production, is described. The key reactions include a double Suzuki-Miyaura coupling of electron-rich aryl bromide with a couple of phenylboronic acids, a Cu-mediated Ullmann reaction, and a LHMDS-promoted phenylacetylation. This synthesis proceeded in 11 steps with 18% overall yield from a known sesamol derivative.
• ——
  作者：V. F. Mironov、R. R. Petrov、A. A. Shtyrlina、A. T. Gubaidullin、I. A. Litvinov、R. Z. Musin、A. I. Konovalov

  DOI：10.1023/a:1012381423101

  日期：——

  According to the NMR, IR, and high-resolution mass spectra, the major products of the reactions of 5,6-dibromo-2-chlorobenzo[d]-1,3,2-dioxaphosphole 2,2-dichloride with arylacetylenes are 4-aryl-6,7-dibromo-2-chloro-5,6-benzo[e]-1,2-oxaphosphorin-3-ene 2-oxides. The steric structure of one of the hydrolysis products, 2-hydroxy-6,7-dibromo-4-phenyl-5,6-benzo[e]-1,2-oxaphosphorin-3-ene 2-oxide, was studied by single crystal X-ray diffraction.