trans-4,4'-bis(tert-butylthio)stilbene | 570421-75-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: trans-4,4'-bis(tert-butylthio)stilbene
• 英文别名: trans-4,4'-bis(t-butylthio)stilbene；1-tert-butylsulfanyl-4-[(E)-2-(4-tert-butylsulfanylphenyl)ethenyl]benzene
• CAS: 570421-75-9
• 化学式: C₂₂H₂₈S₂
• 分子量: 356.596
• InChiKey: QJNRUKODZXIECE-BQYQJAHWSA-N

物化性质

• 熔点：
  159-160 °C (polymorph)(Solv: heptane (142-82-5); plates)
• 沸点：
  480.0±34.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  50.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  trans-4,4'-bis(tert-butylthio)stilbene 在 碘 、 三溴化硼 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 14.0h， 生成 trans-4,4'-bis(S-acetyl)stilbenedithiol
  参考文献：
  名称：

  Thetert-Butyl Moiety—A Base Resistent Thiol Protecting Group Smoothly Replaced by the Labile Acetyl Moiety

  摘要：

  Aryl t-butyl sulfides underwent quantitative tert-butyl/acetyl exchange reactions affording thioacetic acid S-aryl esters when treated with acetyl chloride and boron tribromide.

  DOI：

  10.1081/scc-120015820
• 作为产物：
  描述：

  4-(叔丁基磺酰基)苯甲醛 在 四氯化钛 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以67%的产率得到trans-4,4'-bis(tert-butylthio)stilbene
  参考文献：
  名称：

  Thetert-Butyl Moiety—A Base Resistent Thiol Protecting Group Smoothly Replaced by the Labile Acetyl Moiety

  摘要：

  Aryl t-butyl sulfides underwent quantitative tert-butyl/acetyl exchange reactions affording thioacetic acid S-aryl esters when treated with acetyl chloride and boron tribromide.

  DOI：

  10.1081/scc-120015820

文献信息

• Bromine catalyzed conversion of S-tert-butyl groups into versatile and, for self-assembly processes accessible, acetyl-protected thiols
  作者：Alfred Błaszczyk、Mark Elbing、Marcel Mayor

  DOI：10.1039/b408677e

  日期：——

  The facile and efficient conversion of a tert-butyl protecting group to an acetyl protecting group for thiols by catalytic amounts of bromine in acetyl chloride and the presence of acetic acid has been developed. The fairly mild reaction conditions are of particular interest for new protecting group strategies for sulfur functionalised target structures.

  在乙酰氯和乙酸存在的情况下，通过催化溴的用量，将叔丁基保护基团简便高效地转化为硫醇的乙酰基保护基团。这种相当温和的反应条件对于硫官能化目标结构的新保护基策略具有特别重要的意义。
• Utilization of microwave heating in the McMurry reaction for facile coupling of aldehydes and ketones to give alkenes
  作者：Nicolai Stuhr-Hansen

  DOI：10.1016/j.tetlet.2005.06.057

  日期：2005.8

  Microwave heating was applied in high-yield syntheses of alkenes by McMurry coupling of aldehydes and ketones with low-valent titanium. All aldehydes and ketones including sulfur end-capped analogues gave alkenes in isolated yields above 80% without detectable amounts of pinacols. (c) 2005 Elsevier Ltd. All rights reserved.
• The<b><i>tert</i></b>-Butyl Moiety—A Base Resistent Thiol Protecting Group Smoothly Replaced by the Labile Acetyl Moiety
  作者：Nicolai Stuhr-Hansen

  DOI：10.1081/scc-120015820

  日期：2003.1.4

  Aryl t-butyl sulfides underwent quantitative tert-butyl/acetyl exchange reactions affording thioacetic acid S-aryl esters when treated with acetyl chloride and boron tribromide.