2,2'-dihydroxy-5-nitrobiphenyl | 96661-32-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,2'-dihydroxy-5-nitrobiphenyl
• 英文别名: p-Nitro-biphenol；2-(2-hydroxyphenyl)-4-nitrophenol
• CAS: 96661-32-4
• 化学式: C₁₂H₉NO₄
• 分子量: 231.208
• InChiKey: MLNVRZKTQIQZHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  86.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  二碳酸二叔丁酯 、 2,2'-dihydroxy-5-nitrobiphenyl 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以95%的产率得到di-tert-butyl (5-nitro-[1,1'-biphenyl]-2,2'-diyl) bis(carbonate)
  参考文献：
  名称：

  Synthesis and SAR study of N-(4-hydroxy-3-(2-hydroxynaphthalene-1-yl)phenyl)-arylsulfonamides: Heat shock protein 90 (Hsp90) inhibitors with submicromolar activity in an in vitro assay

  摘要：

  Heat shock protein 90 is emerging as an important target in cancer chemotherapy. In a program directed toward identifying novel chemical probes for Hsp90, we found N-(4-hydroxy-3-(2-hydroxynaphthalene-1-yl)phenyl)benzene sulfonamide as an Hsp90 inhibitor with very weak activity. In this report, we present a new and general method for the synthesis of a variety of analogs around this scaffold, and discuss their structure-activity relationships. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.08.022
• 作为产物：
  描述：

  在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 2,2'-dihydroxy-5-nitrobiphenyl
  参考文献：
  名称：

  Synthesis of Unsymmetrical o-Biphenols and o-Binaphthols via Silicon-Tethered Pd-Catalyzed C−H Arylation

  摘要：

  A mild, practical, and efficient method for the synthesis of unsymmetrical o-biphenols (including o-phenol-naphthols and o-binaphthols) has been developed. Unsymmetrical bis-aryloxy silanes, which were readily prepared in a semi-one-pot fashion, underwent the Pd-catalyzed intramolecular arylation followed by a routine TBAF desilylation step to furnish valuable unsymmetrical biphenols without necessity of isolation of seven-membered intermediates. The excellent functional group tolerance allows for synthesis of a variety of functionalized o-biphenols and o-binaphthols from easily available staring materials.

  DOI：

  10.1021/ol100924n

文献信息

• Phenoxenium ions identical intermediates in the acid-catalyzed solvolysis of n-tosyl-O-Arylhydroxylamines and in the thermolysis of N-Aryloxypyridinium salts
  作者：Hiroyuki Iijima、Yasuyuki Endo、Koichi Shudo、Toshihiko Okamoto

  DOI：10.1016/s0040-4020(01)91336-5

  日期：1984.1

  The acid-catalyzed solvolysis of N-tosyl-O-arylhydroxylamines in aromatic solvents and the thermolysis of N-arylqxypyridinium salts involve common intermediates, phenoxenium ions, for the formation of hydroxybiphenyl derivatives. Diphenylethers are formed when the hydrolysis of the N—O bonds is slow and the aromatic solvent has high nucleophilicity.

  N-甲苯磺酰基-O-芳基羟胺在芳族溶剂中的酸催化溶剂分解和N-芳基氧代吡啶鎓盐的热分解涉及常见的中间体苯氧鎓离子，用于形成羟基联苯衍生物。当N-O键的水解缓慢且芳族溶剂具有高亲核性时，会形成二苯醚。
• IIJIMA, HIROYUKI;ENDO, YASUYUKI;SHUDO, KOICHI;OKAMOTO, TOSHIHIKO, TETRAHEDRON, 1984, 40, N 23, 4981-4985
  作者：IIJIMA, HIROYUKI、ENDO, YASUYUKI、SHUDO, KOICHI、OKAMOTO, TOSHIHIKO

  DOI：——

  日期：——
• Synthesis and SAR study of N-(4-hydroxy-3-(2-hydroxynaphthalene-1-yl)phenyl)-arylsulfonamides: Heat shock protein 90 (Hsp90) inhibitors with submicromolar activity in an in vitro assay
  作者：Thota Ganesh、Pahk Thepchatri、Lian Li、Yuhong Du、Haian Fu、James P. Snyder、Aiming Sun

  DOI：10.1016/j.bmcl.2008.08.022

  日期：2008.9

  Heat shock protein 90 is emerging as an important target in cancer chemotherapy. In a program directed toward identifying novel chemical probes for Hsp90, we found N-(4-hydroxy-3-(2-hydroxynaphthalene-1-yl)phenyl)benzene sulfonamide as an Hsp90 inhibitor with very weak activity. In this report, we present a new and general method for the synthesis of a variety of analogs around this scaffold, and discuss their structure-activity relationships. (C) 2008 Elsevier Ltd. All rights reserved.
• Synthesis of Unsymmetrical <i>o</i>-Biphenols and <i>o</i>-Binaphthols via Silicon-Tethered Pd-Catalyzed C−H Arylation
  作者：Chunhui Huang、Vladimir Gevorgyan

  DOI：10.1021/ol100924n

  日期：2010.5.21

  A mild, practical, and efficient method for the synthesis of unsymmetrical o-biphenols (including o-phenol-naphthols and o-binaphthols) has been developed. Unsymmetrical bis-aryloxy silanes, which were readily prepared in a semi-one-pot fashion, underwent the Pd-catalyzed intramolecular arylation followed by a routine TBAF desilylation step to furnish valuable unsymmetrical biphenols without necessity of isolation of seven-membered intermediates. The excellent functional group tolerance allows for synthesis of a variety of functionalized o-biphenols and o-binaphthols from easily available staring materials.