2-benzyl-3-iodo-4,5-dimethylthiophene | 1393655-63-4

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 2-benzyl-3-iodo-4,5-dimethylthiophene
• CAS: 1393655-63-4
• 化学式: C₁₃H₁₃IS
• 分子量: 328.217
• InChiKey: KSWJAPODUHIURW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  15
• 可旋转键数：
  2
• 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：

  2-mercapto-3-methyl-6-phenyl-hex-4-yn-3-ol 在 碘 、 碳酸氢钠 作用下， 以 乙腈 为溶剂， 反应 5.0h， 以68%的产率得到2-benzyl-3-iodo-4,5-dimethylthiophene
  参考文献：
  名称：

  An Iodocyclization Approach to Substituted 3-Iodothiophenes

  摘要：

  A novel approach to 3-iodothiophenes by direct iodocyclization of alkynylthiol derivatives is presented. A variety of 1-mercapto-3-yn-2-ols 5 (readily available from alkynylation of the corresponding alpha-mercapto ketones or alpha-mercapto esters) were smoothly converted into the corresponding 3-iodothiophene derivatives 6 in good yields by reaction with molecular iodine in the presence of NaHCO3 at room temperature in MeCN as the solvent.

  DOI：

  10.1021/jo301001j

文献信息

• Synthesis of thiophenes in a deep eutectic solvent: heterocyclodehydration and iodocyclization of 1-mercapto-3-yn-2-ols in a choline chloride/glycerol medium
  作者：Raffaella Mancuso、Asif Maner、Luciana Cicco、Filippo M. Perna、Vito Capriati、Bartolo Gabriele

  DOI：10.1016/j.tet.2016.05.062

  日期：2016.7

  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.