2,3-dimethyl-5-p-tolylthiophene | 1403459-97-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 2,3-dimethyl-5-p-tolylthiophene
• 英文别名: 2,3-Dimethyl-5-(4-methylphenyl)thiophene
• CAS: 1403459-97-1
• 化学式: C₁₃H₁₄S
• 分子量: 202.32
• InChiKey: XOXLFVRMMDNQCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-mercapto-3-methyl-1-p-tolylpent-1-yn-3-ol 在 氯化胆碱 、 potassium iodide 、 palladium(II) iodide 作用下， 以 甘油 为溶剂， 反应 8.0h， 以80%的产率得到2,3-dimethyl-5-p-tolylthiophene
  参考文献：
  名称：

  Synthesis of thiophenes in a deep eutectic solvent: heterocyclodehydration and iodocyclization of 1-mercapto-3-yn-2-ols in a choline chloride/glycerol medium

  摘要：

  The heterocyclodehydration and iodocyclization of readily available 1-mercapto-3-yn-2-ols has been performed in a deep eutectic solvent (DES), that is, ChCl/Gly (1:2 molar ratio; ChCl=choline chloride, Gly=glycerol), as a non-conventional green solvent. The processes, carried out at 50 degrees C for 8 h in the presence of the PdI2/KI catalytic system or at room temperature for 5 h with 1.2 equiv of I-2, led to the formation of the corresponding thiophenes and 3-iodothiophenes in good to high yields. The DES/catalytic system could be easily recycled several times without appreciable loss of activity, after extraction of the thiophene product with hexane or Et2O. The alkynylation reaction of alpha-mercapto ketones, necessary for the preparation of the allcynylthiol substrates, was also successfully accomplished in the above protic eutectic mixture competitively with protonolysis. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2016.05.062

文献信息

• Synthesis of Substituted Thiophenes by Palladium-Catalyzed Heterocyclodehydration of 1-Mercapto-3-yn-2-ols in Conventional and Nonconventional Solvents
  作者：Bartolo Gabriele、Raffaella Mancuso、Lucia Veltri、Vito Maltese、Giuseppe Salerno

  DOI：10.1021/jo301943k

  日期：2012.11.2

  A variety of readily available 1-mercapto-3-yn-2-ols 5 were conveniently converted into the corresponding thiophenes 6 in good to high yields in MeOH as the solvent at 50-100 degrees C in the presence of catalytic amounts (1-2%) of PdI2 in conjunction with KI (KI:PdI2 molar ratio = 10). The catalyst could be made recyclable employing an ionic liquid, such as BmimBF(4), as the solvent under suitable conditions.
• Ink composition for color-memorizing photochromic writing instrument and writing instrument using the same
  申请人：Shibahashi Yutaka

  公开号：US20070082977A1

  公开（公告）日：2007-04-12

  An ink composition for a color-memorizing photochromic writing instrument, which comprises a photochromic agent containing a diarylethene photochromic compound dissolved, dispersed or suspended in a vehicle containing at least a solvent and a binder.
• US7575386B2
  申请人：——

  公开号：US7575386B2

  公开（公告）日：2009-08-18
• US8444450B2
  申请人：——

  公开号：US8444450B2

  公开（公告）日：2013-05-21