1,2-bis(4-hydroxyphenyl)diselane | 835629-63-5

• 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(4-hydroxyphenyl)diselane
• 英文别名: bis(4-hydroxyphenyl)diselenide；4,4'-diselanediyl-di-phenol；4,4'-Diselandiyl-di-phenol；Bis-(4-hydroxy-phenyl)-diselenid；Bis(4-hydroxy-phenyl) diselenide；4-[(4-hydroxyphenyl)diselanyl]phenol
• CAS: 835629-63-5
• 化学式: C₁₂H₁₀O₂Se₂
• 分子量: 344.13
• InChiKey: IYMIPGFVFBAPOK-UHFFFAOYSA-N

物化性质

• 熔点：
  134 °C
• 沸点：
  494.2±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(4-hydroxyphenyl)diselane 、 乙酸酐 在 吡啶 作用下， 生成 bis-(4-acetoxy-phenyl)-diselenide
  参考文献：
  名称：

  Keimatsu; Yokota, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1930, vol. 50, p. 531,535; dtsch. Ref. S. 79

  摘要：

  DOI：
• 作为产物：
  描述：

  4-溴苯酚 在 selenium 、 hydrazine hydrate 、 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以62%的产率得到1,2-bis(4-hydroxyphenyl)diselane
  参考文献：
  名称：

  An investigation of in vitro cytotoxicity and apoptotic potential of aromatic diselenides

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2014.05.075

文献信息

• Rhodium-Catalyzed Enantioselective Hydroselenation of Heterobicyclic Alkenes
  作者：Sifeng Li、Qingjing Yang、Zhaoxiang Bian、Jun Wang

  DOI：10.1021/acs.orglett.0c00762

  日期：2020.4.3

  A highly efficient Rh(I)/(S)-xyl-Binap catalytic system is developed for the asymmetric hydroselenation of various nonpolar olefins with diselenides. Under these mild reaction conditions, a wide range of heterobicyclic alkenes give selenol-incorporated adducts in excellent enantioselectivities (up to 97%) along with high yields (up to 96%) by overcoming self-promoted racemic hydroselenation. The strategy

  开发了一种高效的Rh（I）/（S）-xyl-Binap催化体系，用于各种非极性烯烃与二硒化物的不对称加氢精制。在这些温和的反应条件下，通过克服自我促进的外消旋氢硒化作用，各种各样的杂双环烯烃可以使硒醇结合的加合物具有出色的对映选择性（最高97％）和高产率（最高96％）。该策略也适用于不对称的氧杂苯并降冰片二烯的动力学拆分。
• Matti, Bulletin de la Societe Chimique de France, 1940, vol. <5>7, p. 617,620
  作者：Matti

  DOI：——

  日期：——
• Synthesis of bis(4-hydroxyphenyl) selenide and epoxide and acrylate monomers on this basis
  作者：S. V. Balina、V. V. Russkikh、N. A. Orlova、L. N. Ogneva、V. V. Shelkovnikov

  DOI：10.1134/s1070428015020104

  日期：2015.2

  Reaction of SeCl2 with PhOH has afforded bis(4-hydroxyphenyl) selenide, whose treatment with epichlorohydrin provides a diepoxide that is transformed in bisacrylate and further in tetraacrylate via opening of the epoxide rings with acrylic acid followed by acylation with acryloyl chloride.
• Keimatsu; Yokota, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1930, vol. 50, p. 531,535; dtsch. Ref. S. 79
  作者：Keimatsu、Yokota

  DOI：——

  日期：——
• 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.