2-Methyl-4-(2,4,5-trimethyl-thiophen-3-yl)-but-3-yn-2-ol | 880160-00-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 2-Methyl-4-(2,4,5-trimethyl-thiophen-3-yl)-but-3-yn-2-ol
• 英文别名: 2-methyl-4-(2,4,5-trimethylthiophen-3-yl)but-3-yn-2-ol
• CAS: 880160-00-9
• 化学式: C₁₂H₁₆OS
• 分子量: 208.324
• InChiKey: BOSXCZMZDXUIFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-Methyl-4-(2,4,5-trimethyl-thiophen-3-yl)-but-3-yn-2-ol 在 copper(l) iodide sodium hydroxide 、 四(三苯基膦)钯 、 偶氮二异丁腈 、 苄基三乙基氯化铵 作用下， 以 甲苯 、 苯 为溶剂， 反应 20.0h， 生成 4,5-Bis-(2,4,5-trimethyl-thiophen-3-yl)-[1,3]dithiol-2-one
  参考文献：
  名称：

  Synthesis and Photochromic Properties of Functional Diarylethenes with a [1,3]dithiol-2-one (Thione) Bridging Unit

  摘要：

  In designing new photochromic compounds for optical data storage and photo-switching devices, the synthesis of a series of 4,5-diaryl-1,3-dithiol-2-one and 4,5-diaryl-1,3-dithiol-2-thione, which are suitable building blocks for incorporation with fluorophore, is herein reported. Our strategy needs the preliminary preparation of diarylalkynes, obtained by successive Sonogashira-Hagihara coupling-reactions in good yields (63-92%). A combination of these synthetic precursors with diisopropylxanthogen disulfide leads to the corresponding 4,5-diaryl-1,3-dithiol-2-ones under radical conditions with excellent yields (54-70%). The thionation of these compounds is obtained nearly quantitatively with phosphorous pentasulfide.

  DOI：

  10.1080/15421400590946451
• 作为产物：
  描述：

  3-碘-2,4,5-三甲基噻吩 、 2-甲基-3-丁炔-2-醇 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 二乙胺 作用下， 反应 15.0h， 以85%的产率得到2-Methyl-4-(2,4,5-trimethyl-thiophen-3-yl)-but-3-yn-2-ol
  参考文献：
  名称：

  Synthesis and Photochromic Properties of Functional Diarylethenes with a [1,3]dithiol-2-one (Thione) Bridging Unit

  摘要：

  In designing new photochromic compounds for optical data storage and photo-switching devices, the synthesis of a series of 4,5-diaryl-1,3-dithiol-2-one and 4,5-diaryl-1,3-dithiol-2-thione, which are suitable building blocks for incorporation with fluorophore, is herein reported. Our strategy needs the preliminary preparation of diarylalkynes, obtained by successive Sonogashira-Hagihara coupling-reactions in good yields (63-92%). A combination of these synthetic precursors with diisopropylxanthogen disulfide leads to the corresponding 4,5-diaryl-1,3-dithiol-2-ones under radical conditions with excellent yields (54-70%). The thionation of these compounds is obtained nearly quantitatively with phosphorous pentasulfide.

  DOI：

  10.1080/15421400590946451