bis(p-hydroxyphenyl)selane | 141982-42-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: bis(p-hydroxyphenyl)selane
• 英文别名: 4-(4-hydroxyphenylselanyl)phenol；bis(4-hydroxyphenyl)diselenide；p-selenophenol；4,4'-selanediyl-di-phenol；Bis-(4-hydroxy-phenyl)-selenid；4,4'-Selandiyl-di-phenol；Bis(p-hydroxyphenyl) selenide；4-(4-hydroxyphenyl)selanylphenol
• CAS: 141982-42-5
• 化学式: C₁₂H₁₀O₂Se
• 分子量: 265.17
• InChiKey: KIKDXUSFMAWUGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.75
• 重原子数：
  15
• 可旋转键数：
  2
• 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：

  bis(p-hydroxyphenyl)selane 在 苄基三乙基氯化铵 、 三乙胺 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 13.0h， 生成 1-[4-({4-[2,3-bis(prop-2-enoyloxy)propoxy]phenyl}selanyl)phenoxy]-3-(prop-2-enoyloxy)-propan-2-yl prop-2-enoate
  参考文献：
  名称：

  Synthesis of bis(4-hydroxyphenyl) selenide and epoxide and acrylate monomers on this basis

  摘要：

  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.

  DOI：

  10.1134/s1070428015020104
• 作为产物：
  描述：

  4-碘苯酚 在 copper(I) oxide 、 selenium 、 乙二胺 、 potassium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 1.0h， 以58%的产率得到bis(p-hydroxyphenyl)selane
  参考文献：
  名称：

  Microwave-assisted Cu2O-catalyzed one-pot synthesis of symmetrical diaryl selenides from elemental selenium

  摘要：

  A novel and simple microwave-assisted one-pot protocol to prepare symmetrical diary] selenides has been developed. A cross-coupling reaction between aryl iodide and elemental selenium takes place in the presence of KOH and a catalytic amount of Cu2O/NH2CH2CH2NH2, leading to C-Se bond formation. The reactions are highly efficient with a reaction time of 1 h under microwave irradiation and yields from 50% to 90%. Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2013.06.117

文献信息

• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Se: MVol.B, 25, page 51 - 54
  作者：

  DOI：——

  日期：——
• Takamatsu, M., 1928, p. 450 - 450
  作者：Takamatsu, M.

  DOI：——

  日期：——
• Keimatsu; Yokota, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1931, vol. 51, p. 1007,1009, 1015; dtsch. Ref. 52 <1932> 19, 22
  作者：Keimatsu、Yokota

  DOI：——

  日期：——
• Microwave-assisted Cu2O-catalyzed one-pot synthesis of symmetrical diaryl selenides from elemental selenium
  作者：Shaozhong Zhang、Kranthi Karra、Christina Heintz、Erica Kleckler、Jin Jin

  DOI：10.1016/j.tetlet.2013.06.117

  日期：2013.8

  A novel and simple microwave-assisted one-pot protocol to prepare symmetrical diary] selenides has been developed. A cross-coupling reaction between aryl iodide and elemental selenium takes place in the presence of KOH and a catalytic amount of Cu2O/NH2CH2CH2NH2, leading to C-Se bond formation. The reactions are highly efficient with a reaction time of 1 h under microwave irradiation and yields from 50% to 90%. Published by Elsevier Ltd.
• 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.