1,2-bis(2-hydroxyphenyl)diselenide | 73011-32-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 1,2-bis(2-hydroxyphenyl)diselenide
• 英文别名: 1,2-bis(2-hydroxyphenyl)diselane；bis(2-hydroxyphenyl) diselenide；bis(2-hydroxyphenyl)diselenide；2,2'-diselenidediyldiphenol；2-[(2-Hydroxyphenyl)diselanyl]phenol
• CAS: 73011-32-2
• 化学式: C₁₂H₁₀O₂Se₂
• 分子量: 344.13
• InChiKey: WXLMISPTCQITOI-UHFFFAOYSA-N

物化性质

• 熔点：
  65.0-66.5 °C(Solv: cyclohexane (110-82-7); toluene (108-88-3))
• 沸点：
  462.1±55.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.37
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• 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：

  1,2-bis(2-hydroxyphenyl)diselenide 在 偶氮二甲酸二异丙酯 、 溴 、 三苯基膦 作用下， 以 四氢呋喃 、 四氯化碳 、 二氯甲烷 、 甲苯 为溶剂， 反应 3.83h， 生成 ethyl (2R)-2-(2-{[2-methoxy-2-(m-tolyl)ethyl]selanyl}phenoxy)propanoate
  参考文献：
  名称：

  手性硒亲电子试剂的不对称甲氧基硒化

  摘要：

  制备了非常简单的手性非外消旋二硒化物，并将其相应的硒亲电试剂用于烯烃的立体选择性功能化。研究了不同烯烃对硒基化反应结果的影响。

  DOI：

  10.1002/ejoc.201101373
• 作为产物：
  描述：

  2-溴苯酚 在 正丁基锂 、 四甲基乙二胺 、 selenium 作用下， 以 正己烷 为溶剂， 反应 26.5h， 以35%的产率得到1,2-bis(2-hydroxyphenyl)diselenide
  参考文献：
  名称：

  手性硒亲电子试剂的不对称甲氧基硒化

  摘要：

  制备了非常简单的手性非外消旋二硒化物，并将其相应的硒亲电试剂用于烯烃的立体选择性功能化。研究了不同烯烃对硒基化反应结果的影响。

  DOI：

  10.1002/ejoc.201101373

文献信息

• An Efficient One-Pot Synthesis of Symmetrical Diselenides or Ditellurides from Halides with CuO Nanopowder/Se⁰ or Te⁰/Base
  作者：Devender Singh、Anna M. Deobald、Leandro R. S. Camargo、Greice Tabarelli、Oscar E. D. Rodrigues、Antonio L. Braga

  DOI：10.1021/ol100558b

  日期：2010.8.6

  A CuO nanopowder-catalyzed coupling reaction of aryl, alkyl, and heteroaryl iodides with elemental selenium and tellurium takes place in the presence of KOH at 90 degrees C In DMSO. A wide range of substituted symmetrical diselenides and ditellurides were afforded with good to excellent yields.
• Synthesis of novel organoselenium as catalyst for Baeyer–Villiger oxidation with 30% H2O2
  作者：Hayato Ichikawa、Yoshihide Usami、Masao Arimoto

  DOI：10.1016/j.tetlet.2005.10.055

  日期：2005.12

  A novel diselenide was synthesized in good yield via only four steps from phenol, and was employed as the catalyst for the Baeyer-Villiger oxidation with 30% H2O2 to obtain lactones in good yields. (c) 2005 Elsevier Ltd. All rights reserved.
• Functionalized alkyl and aryl diselenides as antimicrobial and antiviral agents: synthesis and properties
  作者：H Wójtowicz、M Chojnacka、J Młochowski、J Palus、L Syper、D Hudecova、M Uher、E Piasecki、M Rybka

  DOI：10.1016/j.farmac.2003.08.003

  日期：2003.12

  The different dialkyl and diaryl diselenides with carbamoyl and sulfamoyl moieties 2, 3, 5 and other substituents in the ortho position of benzene ring 4, 7, 8 as well as derivatives of 1,2,4-benzoselenadiazine (6) were designed as antiviral and antimicrobial agents and synthesized. Some of them, particularly 8a and 8b, were found in the antiviral assay in vitro to be strong inhibitors of cytopathic activity encephalomyocarditis virus (EMCV). The compound 4a and 8a were found to have a broad spectrum of acivity against bacteria, yeasts and pathogenic fungi in vitro.
• Asymmetric Methoxyselenenylations with Chiral Selenium Electrophiles
  作者：Liwei Zhao、Zhong Li、Thomas Wirth

  DOI：10.1002/ejoc.201101373

  日期：2011.12

  Very simple, chiral, non-racemic diselenides were prepared and their corresponding selenium electrophiles were used for the stereoselective functionalization of alkenes. The influence of different alkenes on the outcome of the selenenylation reaction was investigated.

  制备了非常简单的手性非外消旋二硒化物，并将其相应的硒亲电试剂用于烯烃的立体选择性功能化。研究了不同烯烃对硒基化反应结果的影响。
• An investigation of in vitro cytotoxicity and apoptotic potential of aromatic diselenides
  作者：Masood Ahmad Rizvi、Santosh Guru、Tahira Naqvi、Manjeet Kumar、Navanath Kumbhar、Showkat Akhoon、Shazia Banday、Shashank K. Singh、Shashi Bhushan、G. Mustafa Peerzada、Bhahwal Ali Shah

  DOI：10.1016/j.bmcl.2014.05.075

  日期：2014.8

  A target synthesis of a library of symmetric aromatic diselenides was attempted with the aim of generating anticancer lead compounds. Out of thirteen screened molecules (1-13) against a panel of human cancer cell lines, compound 8 exhibited highest cell growth inhibition in Human leukemia HL-60 cells with IC50 value of 8 mu M. Compound 8 had a good pro-apoptotic potential as evidenced from several apoptotic protocols like DNA cell cycle analysis and monitoring of apoptotic bodies formation using phase contrast and nuclear microscopy with Hoechst 33,258. Also, 8 significantly inhibits S phase of the cell cycle and eventually trigger apoptosis in HL-60 cells through mitochondrial dependent pathway substantiated by the loss of mitochondrial potential. A theoretical investigation of DNA binding ability of 8 showed that it selectively bind to minor groove of DNA, where it is stabilized by hydrogen bonding and hydrophobic interactions. (C) 2014 Elsevier Ltd. All rights reserved.