2-[bis(ethylsulfanyl)methyl]thiophene

• 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-[bis(ethylsulfanyl)methyl]thiophene
• 化学式: C₉H₁₄S₃
• 分子量: 218.408
• InChiKey: HPJBIDBGWHZORV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  78.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-噻吩甲醛 、 乙硫醇 在 三甲基氯硅烷 作用下， 反应 1.5h， 以68%的产率得到2-[bis(ethylsulfanyl)methyl]thiophene
  参考文献：
  名称：

  Synthesis of Open-Chain Dithioacetals from Thiophene-2-carbaldehyde and Its Analogs

  摘要：

  基于噻吩-2-甲醛及其类似物与硫醇在氯三甲基硅烷中的反应，开发了一种合成含有各种噻吩片段的二硫缩醛类化合物的方法。

  DOI：

  10.1007/s11178-005-0275-y

文献信息

• Eco-friendly and Highly Chemoselective 1,3-Oxathio- and 1,3-Dithioacetalization of Aldehydes Using Ionic Liquids
  作者：J. S. Yadav、B. V. S. Reddy、G. Kondaji

  DOI：10.1246/cl.2003.672

  日期：2003.8

  Room temperature ionic liquids have been employed for the first time as novel and recyclable reaction media for the chemoselective conversion of aldehydes into their corresponding 1,3-oxathio- and dithioacetal derivatives in excellent yields under mild and neutral conditions. A wide range of functional and protecting groups such as TBDMS, PMB, THP, MOM, benzyl, propargyl ethers, acetonides, carbamates and esters are survived under these reaction conditions. The recovered activated ionic liquids can be recycled for four to five subsequent runs with consistency in activity.

  室温离子液体首次被用作新型且可回收的反应介质，用于在温和中性条件下将醛选择性转化为相应的1,3-氧硫杂环和二硫杂环衍生物，产率极佳。在这些反应条件下，包括TBDMS、PMB、THP、MOM、苄基、炔丙基醚、乙缩醛、氨基甲酸酯和酯等多种功能性和保护性官能团都能稳定存在。回收的活性离子液体可循环用于后续四到五次反应，活性保持一致。
• Simple, Mild and Efficient Thioacetalization and Transthioacetalization of Carbonyl Compounds and Deprotection of Thioacetals: Unique Role of Thiols in the Selectivity of Thioacetalization
  作者：Biswanath Das、Ravirala Ramu、Majjigapu Ravinder Reddy、Gurram Mahender

  DOI：10.1055/s-2004-834934

  日期：——

  Silica supported sodium hydrogen sulfate (NaHSO 4 .SiO 2 ) has been employed for efficient thioacetalization and transthioacetalization of carbonyl compounds in CH 2 Cl 2 at room temperature. Selectivity of thioacetalization was dependent on the thiols used for the conversion. The same catalyst was also found to be effective for deprotection of thioacetals in CH 2 Cl 2 -H 2 O at room temperature.

  二氧化硅负载的硫酸氢钠 (NaHSO 4 .SiO 2 ) 已被用于在室温下在 CH 2 Cl 2 中对羰基化合物进行有效的硫缩醛化和转硫缩醛化。硫缩醛化的选择性取决于用于转化的硫醇。还发现相同的催化剂在室温下在 CH 2 Cl 2 -H 2 O 中对硫缩醛的脱保护有效。
• Investigations Towards the Chemoselective Thioacetaliztion of Carbonyl Compounds by Using Ionic Liquid[bmim]Br as a Recyclable Catalytic Medium
  作者：Ahmed Kamal、Gagan Chouhan

  DOI：10.1002/adsc.200303171

  日期：2004.4

  The ionic liquid based on the 1-n-butyl-3-methylimidazolium cation has been prepared and used as an efficient catalytic medum for the chemoselective thioacetalization of carbonyl compounds. Furthermore, recycling and reuse of this ionic liquid medium has been demonstrated. Moreover, the use of this catalytic medium not only avoids the generation of waste but also provides a green process with minimal

  已经制备了基于1-正丁基-3-甲基咪唑鎓阳离子的离子液体，并将其用作羰基化合物的化学选择性硫缩醛化的有效催化介质。此外，已经证明了该离子液体介质的再循环和再利用。此外，使用这种催化介质不仅避免了废物的产生，而且还提供了危害最小的绿色工艺。
• Reactions of Thiophene-2-carbaldehydes with Thiols in the Presence of Chlorotrimethylsilane
  作者：L. K. Papernaya、E. P. Levanova、E. N. Sukhomazova、A. I. Albanov、E. N. Deryagina

  DOI：10.1023/b:rujo.0000010577.50576.d6

  日期：2003.10
• Chemoselective thioacetalization and transthioacetalization of carbonyl compounds catalyzed by immobilized scandium(III) triflate in ionic liquids
  作者：Ahmed Kamal、Gagan Chouhan

  DOI：10.1016/s0040-4039(03)00580-x

  日期：2003.4

  Immobilized scandium triflate [Sc(OTf)(3)] in ionic liquids has been found to be an extremely efficient and recyclable catalyst for the thioacetalization and transthioacetalization of both aromatic and aliphatic aldehydes. Significant rate acceleration and chemoselectivity was achieved by employing this catalytic system. (C) 2003 Elsevier Science Ltd. All rights reserved.