3,3'-diisobutyl-α,α'-bithiophene | 786457-11-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: 3,3'-diisobutyl-α,α'-bithiophene
• 英文别名: 3,4'-bis(2-methylpropyl)-2,2'-bithiophene；3,4'-diisobutyl-2,2'-bithiophene；3-(2-Methylpropyl)-2-[4-(2-methylpropyl)thiophen-2-yl]thiophene
• CAS: 786457-11-2
• 化学式: C₁₆H₂₂S₂
• 分子量: 278.483
• InChiKey: ASJIYJGNURSPMW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,3'-diisobutyl-α,α'-bithiophene 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以95%的产率得到2-bromo-4,4'-diisobutyl-α,α'-bithiophene
  参考文献：
  名称：

  Oligothiophene Isocyanides for Platinum-Based Molecular Electronic Applications

  摘要：

  Understanding molecular orientation on a metal surface is key to designing molecular electronic device junctions. Though platinum device electrodes are of particular interest as a more stable alternative to the often used gold electrodes, the chemisorption of conducting molecules onto platinum surfaces has not been thoroughly studied. We present herein the first detailed study of the ability and manner in which soluble oligothiophene isocyanides, of lengths ranging from 2 to 7 nm, chemisorb onto platinum surfaces and nanoparticles. It was found that these oligothiophene isocyanides stand at a 41 degrees angle from the platinum surface normal, suggesting their applicability in molecule-bridged platinum electrode devices.

  DOI：

  10.1021/ja045904p
• 作为产物：
  描述：

  3-(isobutyl)thiophene 在 1,3,5,7-tetrakis[4-{hydroxy(tosyloxy)iodo}phenyl]adamantane 、 三甲基溴硅烷 作用下， 以 六氟异丙醇 为溶剂， 反应 2.0h， 以71%的产率得到3,3'-diisobutyl-α,α'-bithiophene
  参考文献：
  名称：

  使用可回收的高价碘（III）试剂，通过无金属的氧化偶合反应，可以干净，直接地合成α，α'-联噻吩和联吡咯。

  摘要：

  使用具有金刚烷或甲烷结构的可循环使用的高价碘（III）试剂已经实现了噻吩与吡咯的简便，清洁的氧化联芳基偶联反应。这些碘（III）试剂可以通过简单的固液分离即过滤从反应混合物中回收。

  DOI：

  10.1248/cpb.57.710

文献信息

• Hypervalent iodine(III): selective and efficient single-electron-transfer (SET) oxidizing agent
  作者：Toshifumi Dohi、Motoki Ito、Nobutaka Yamaoka、Koji Morimoto、Hiromichi Fujioka、Yasuyuki Kita

  DOI：10.1016/j.tet.2009.10.040

  日期：2009.12

  ethers, affording the corresponding aromatic cation radicals. Since then, hypervalent iodine(III) has been utilized as a selective and efficient SET oxidizing agent that enables a variety of direct C–H functionalizations of aromatic rings in electron-rich arenes under mild conditions. We have now extended the original method to work in a series of heteroaromatic compounds such as thiophenes, pyrroles,

  1994年，我们首先确定了苯基碘（III）双（三氟乙酸盐）（PIFA）对苯基醚的单电子转移（SET）氧化能力，提供了相应的芳族阳离子自由基。从那时起，高价碘（III）已被用作一种选择性和高效的SET氧化剂，可在温和条件下在富电子芳烃中实现芳环的各种直接C–H官能化。现在，我们已经将原始方法扩展为可用于一系列杂芳族化合物，例如噻吩，吡咯和吲哚。本文总结了自本世纪初以来的调查和结果。
• Clean and Direct Synthesis of .ALPHA.,.ALPHA.'-Bithiophenes and Bipyrroles by Metal-Free Oxidative Coupling Using Recyclable Hypervalent Iodine(III) Reagents
  作者：Toshifumi Dohi、Koji Morimoto、Chieko Ogawa、Hiromichi Fujioka、Yasuyuki Kita

  DOI：10.1248/cpb.57.710

  日期：——

  The facile and clean oxidative biaryl coupling reaction of thiophenes and pyrroles has been achieved using the recyclable hypervalent iodine(III) reagents having adamantane or methane structures. These iodine(III) reagents could be recovered from the reaction mixtures by a simple solid-liquid separation, i.e., filtration.

  使用具有金刚烷或甲烷结构的可循环使用的高价碘（III）试剂已经实现了噻吩与吡咯的简便，清洁的氧化联芳基偶联反应。这些碘（III）试剂可以通过简单的固液分离即过滤从反应混合物中回收。
• The synthesis of head-to-tail (H–T) dimers of 3-substituted thiophenes by the hypervalent iodine(iii)-induced oxidative biaryl coupling reaction
  作者：Toshifumi Dohi、Koji Morimoto、Yorito Kiyono、Akinobu Maruyama、Hirofumi Tohma、Yasuyuki Kita

  DOI：10.1039/b503058g

  日期：——

  The head-to-tail (H-T) dimers could be obtained selectively by the oxidative coupling reaction of 3-substituted thiophenes using a combination of hypervalent iodine(III) reagents and trimethylsilyl trifluoromethanesulfonate.

  通过使用高价碘（III）试剂和三甲基甲硅烷基三氟甲磺酸盐的组合，通过3-取代的噻吩的氧化偶联反应，可以选择性地获得头对尾（HT）二聚体。
• Metal-Free Regioselective Oxidative Biaryl Coupling Leading to Head-to-Tail Bithiophenes: Reactivity Switching, a Concept Based on the Iodonium(III) Intermediate
  作者：Koji Morimoto、Nobutaka Yamaoka、Chieko Ogawa、Tomofumi Nakae、Hiromichi Fujioka、Toshifumi Dohi、Yasuyuki Kita

  DOI：10.1021/ol101498r

  日期：2010.9.3

  A new synthetic concept for obtaining unsymmetrical biaryl coupling products by an oxidative method is reported. Our synthetic strategy casts light on the reaction intermediate for switching the reactivity of 3-substituted thiophenes. On the basis of this strategy, a novel direct method for the synthesis of head-to-tail bithiophenes using hypervalent iodine(III) reagents has been developed.
• Metal-Free Oxidative Coupling Reactions via σ-Iodonium Intermediates: The Efficient Synthesis of Bithiophenes Using Hypervalent Iodine Reagents
  作者：Koji Morimoto、Tomofumi Nakae、Nobutaka Yamaoka、Toshifumi Dohi、Yasuyuki Kita

  DOI：10.1002/ejoc.201100969

  日期：2011.11

  The direct oxidative biaryl coupling reaction is an attractive tool for environmentally benign green chemistry. A novel direct method for the synthesis of bithiophene using a hypervalent iodine reagent has been developed. The reaction mechanism has also been investigated, casting light on the reaction intermediate and revealing the reactivity with iodonium salts.

  直接氧化联芳基偶联反应是一种对环境友好的绿色化学有吸引力的工具。已经开发了一种使用高价碘试剂合成联噻吩的新型直接方法。还研究了反应机理，揭示了反应中间体并揭示了与碘盐的反应性。