3-(octylsulfanyl)thiophene | 120186-62-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3-(octylsulfanyl)thiophene
• 英文别名: octyl 3-thienyl sulfide；3-octylmercapto-thiophene；3-Octylmercapto-thiophen；3-octylsulfanylthiophene
• CAS: 120186-62-1
• 化学式: C₁₂H₂₀S₂
• 分子量: 228.423
• InChiKey: IWBMDDCNOXVMRI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  14
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  53.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(octylsulfanyl)thiophene 在 四(三苯基膦)钯 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 、 溶剂黄146 、 甲苯 为溶剂， 反应 75.0h， 生成 4-(octylsulfanyl)-5,5'-bis(trimethylsilyl)-2,2'-bithiophene
  参考文献：
  名称：

  One-Pot Synthesis of Symmetric Octithiophenes from Asymmetric β-Alkylsulfanyl Bithiophenes

  摘要：

  Starting from 4-(octylsulfanyl)-2,2'-bithiophene, 4-bromo-4'-(octylsulfanyl)-2,2'-bithiophene, 4-iodo-4'-(octylsulfanyl)-2,2'-bithiophene, 4-bromo-4'-[(S)-2-methylbutylsulfanyl]-2,2'-bithiophene, and 4-iodo-4'-[(S)-2-methylbutylsulfanyl]-2,2'-bithiophene, a new series of symmetrically beta-substituted octithiophenes were synthesized by one-pot oxidative coupling with FeCl3. The octithiophenes obtained are soluble in common organic solvents and show different solvatochromic properties depending on the substitution type. In particular, the bromine atom exerts a positive influence on the supramolecular organization: the brominated octithiophenes display high filmability, solvatochromism, and CD induced by aggregation (when the chiral 2-methylbutylsulfanyl group is present), properties usually observed for polythiophenes. Density functional theory (DFT) calculations were carried out an a model bithiophene (4-substituted with a methylsulfanyl group) in order to understand the possible mechanism of the growth, the regiochemistry, and the reason for the polymerization leads to an octithiophene.

  DOI：

  10.1021/ma0614141
• 作为产物：
  描述：

  3-甲氧基噻吩 、 1-辛硫醇 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 20.0h， 以93%的产率得到3-(octylsulfanyl)thiophene
  参考文献：
  名称：

  One-Pot Synthesis of Symmetric Octithiophenes from Asymmetric β-Alkylsulfanyl Bithiophenes

  摘要：

  Starting from 4-(octylsulfanyl)-2,2'-bithiophene, 4-bromo-4'-(octylsulfanyl)-2,2'-bithiophene, 4-iodo-4'-(octylsulfanyl)-2,2'-bithiophene, 4-bromo-4'-[(S)-2-methylbutylsulfanyl]-2,2'-bithiophene, and 4-iodo-4'-[(S)-2-methylbutylsulfanyl]-2,2'-bithiophene, a new series of symmetrically beta-substituted octithiophenes were synthesized by one-pot oxidative coupling with FeCl3. The octithiophenes obtained are soluble in common organic solvents and show different solvatochromic properties depending on the substitution type. In particular, the bromine atom exerts a positive influence on the supramolecular organization: the brominated octithiophenes display high filmability, solvatochromism, and CD induced by aggregation (when the chiral 2-methylbutylsulfanyl group is present), properties usually observed for polythiophenes. Density functional theory (DFT) calculations were carried out an a model bithiophene (4-substituted with a methylsulfanyl group) in order to understand the possible mechanism of the growth, the regiochemistry, and the reason for the polymerization leads to an octithiophene.

  DOI：

  10.1021/ma0614141

文献信息

• Facile Preparation of Aryl Sulfides Using Palladium Catalysis under Mild Conditions
  作者：Tatsuo Okauchi、Kouji Kuramoto、Mitsuru Kitamura

  DOI：10.1055/s-0030-1259012

  日期：2010.12

  A convenient method for C-S cross-coupling of aryl bromides with various thiols has been developed that involves the use of a 1,1'-bis(diphenylphosphino)ferrocene (DPPF)-ligated palladium complex with N,N-diisopropylethylamine (DIPEA) as the base. This coupling is tolerant of a wide range of functional groups, including hydroxy, amino, cyano, nitro, formyl, and carboxyl groups.

  已开发出一种用于芳基溴化物与各种硫醇的 CS 交叉偶联的便捷方法，该方法涉及使用 1,1'-双（二苯基膦基）二茂铁 (DPPF)-连接的钯配合物与 N,N-二异丙基乙胺 (DIPEA) 作为基地。这种偶联可耐受多种官能团，包括羟基、氨基、氰基、硝基、甲酰基和羧基。