thiophen-3-ylmethanethiol | 16406-94-3

• 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: thiophen-3-ylmethanethiol
• 英文别名: thien-3-yl-methanethiol；thiophene-3-methylthiol；3-mercaptomethyl-thiophene；3-Thenylthiol；3-Thiophenemethanethiol
• CAS: 16406-94-3
• 化学式: C₅H₆S₂
• 分子量: 130.235
• InChiKey: DFLKSYRDWXWBBL-UHFFFAOYSA-N

物化性质

• 沸点：
  204.8±15.0 °C(Predicted)
• 密度：
  1.191±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  29.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  thiophen-3-ylmethanethiol 在 溴 、 potassium hydrogencarbonate 作用下， 以90%的产率得到3-Thienylmethyl disulfide
  参考文献：
  名称：

  合成这些 Et Etude Electrochimique De Disulfures Thiopheniques

  摘要：

  已经制备了具有噻吩单元的不对称和环状二硫化物。电化学研究表明，由于第二个氧化位点，它们的行为相对于噻吩母体发生了改变。它们中的一些的聚合导致电活性材料。描述了二噻吩并[3,2-c:2',3'-e][1,2] 二噻英的一种新的高效合成方法。

  DOI：

  10.1080/104265090969595
• 作为产物：
  描述：

  3-噻吩甲醛 在 potassium ethyl xanthogenate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 150.0 ℃ 、101.33 kPa 条件下， 生成 thiophen-3-ylmethanethiol
  参考文献：
  名称：

  黄原酸钾促进的还原硫化反应：从醛到硫醇、二硫化物和硫酯衍生物

  摘要：

  在此，我们开发了一种直接构建C-S键以获得具有生物活性的含硫化合物的合成策略，以及一种涉及醛或酮的还原硫化以获得多种取代的硫醇、二硫化物和硫酯衍生物的方法。 EtOCS 2 K 被证明可以作为 Berzelius 试剂或 Lawesson 试剂构建 C-S 键的潜在替代品。

  DOI：

  10.1039/d3cc05637f

文献信息

• Iodine-catalyzed Direct Thiolation of Indoles with Thiols Leading to 3-Thioindoles Using Air as the Oxidant
  作者：Xiaoxia Liu、Huanhuan Cui、Daoshan Yang、Shicui Dai、Guoqin Zhang、Wei Wei、Hua Wang

  DOI：10.1007/s10562-016-1798-2

  日期：2016.9

  A simple and convenient method has been developed for the construction of 3-thioindoles via molecular iodine-catalyzed direct thiolation of indoles with thiols. The present protocol, which employs thiols as the thiolating agents, inexpensive molecular iodine as the catalyst, and environmentally benign air as the oxidant, allows the regioselective generation of 3-thioindoles in good to excellent yields

  已经开发了一种简单方便的方法，用于通过分子碘催化吲哚与硫醇的直接硫醇化来构建 3-硫代吲哚。本协议采用硫醇作为硫醇化剂，廉价的分子碘作为催化剂，环境友好的空气作为氧化剂，允许区域选择性生成 3-硫代吲哚，收率良好。图形摘要
• Thienyl and thenyl alkyl disulfides: monomers and polymers
  作者：V. Duchenet、C. G. Andrieu、J.-M. Catel、G. Le Coustumer、J.-F. Penneau、G. Le Guillanton、P. Hapiot、P. Audebert

  DOI：10.1051/jcp:1998253

  日期：1998.6

  Thienyl and thenyl alkyl disulfides are synthesized by reaction between a mercaptan and dialkylazodicarboxylate; the addition of a second mercaptan gives the unsymmetrical disulfide. The cyclic disulfide, dithieno[3,2-c:2',3'-e] [1,2] dithiin is obtained from the 2,2'-dibromobithiophene. These thiophene derivatives including a second redox system are potential precursors for polymers. Chemical polymerization affords new materials.

  噻烷基和噻烷基烷基二硫化物通过某种巯烷与双烷基偶氮二羧酸酯反应合成；加入第二种巯烷可得到不对称二硫化物。循环二硫化物，双噻唑[3,2-c:2',3'-e][1,2]噻啉由2,2'-二溴双噻吩得到。这些噻吩衍生物包括第二种氧化还原系统，是潜在的聚合物前体。化学聚合可以得到新材料。
• 1-Aryl-2-(1-imidazolyl) alkyl ethers and thioethers
  申请人：Pfizer Inc.

  公开号：US04062966A1

  公开（公告）日：1977-12-13

  Novel 1-aryl-2-(1-imidazolyl)alkyl ethers and thioethers having anti-fungal properties are disclosed.

  揭示了具有抗真菌性能的新型1-芳基-2-(1-咪唑基)烷基醚和硫醚。
• Synthesis of bis(ethylenedithio)tetrathiafulvalene (BEDT-TTF) derivatives functionalised with two, four or eight hydroxyl groups
  作者：R. James Brown、Andrew C. Brooks、Jon-Paul Griffiths、Betrand Vital、Peter Day、John D. Wallis

  DOI：10.1039/b709823e

  日期：——

  Short synthetic routes to a range of BEDT-TTF derivatives functionalised with two, four or eight hydroxyl groups are reported, of interest because of their potential for introducing hydrogen bonding between donor and anion into their radical cation salts. The cycloaddition of 1,3-dithiole-2,4,5-trithione with alkenes to construct 5,6-dihydro-1,3-dithiolo[4,5-b]1,4-dithiin-2-thiones is a key step, with

  据报道，合成短程合成一系列用两个，四个或八个羟基官能化的BEDT-TTF衍生物的途径之所以引起人们的关注，是因为它们具有将供体和阴离子之间的氢键引入其自由基阳离子盐的潜力。1,3-二硫代2,4,5-三硫酮与烯烃的环加成反应以构建5,6-二氢-1,3-二硫代[4,5-b] 1,4-二硫代-2-硫酮是关键步骤，通过均相或异相偶联程序和O-脱保护完成合成。四（羟甲基）BEDT-TTF的单个非对映异构体的首次合成是顺式，反式产物，这是通过仔细选择O保护基团来促进均相和异偶合产物的分离而实现的。三硫酮与对映体1R，2R，5R，6R-双（O，O-异亚丙基）己-3-烯-1,2,5，的环化，
• Free-Radical Addition of Heteroarenethiols and Heteroarylmethanethiols to Hexyne and Phenylacetylene. Chemical Behavior of the Transient .beta.-Sulfanylvinyl Radicals
  作者：Luisa Benati、Laura Capella、Pier Carlo Montevecchi、Piero Spagnolo

  DOI：10.1021/jo00129a039

  日期：1995.12

  The free-radical reaction of a number of heteroarenethiols (including 2-thiophene-, 2-benzo[b]furan-and 2-benzo[b]thiophenethiol) and heteroarylmethanethiols (including 2-furyl-, 2-thienyl-, and 3-thienylmethanethiol) with hex-1-yne and phenylacetylene has been investigated in benzene solution both at 100 degrees C in the presence of AIBN and at room temperature in the presence of BEt(3)/O-2. Under both of these conditions the above thiols generally furnished transient 2-sulfanylvinyl radicals through regioselective addition of corresponding sulfanyl radicals to the terminal alkyne carbon, but 2-benzo[b]furanthiol failed to react with either alkyne in the presence of BEt(3)/O-2 and unexpectedely gave 2-(ethylsulfanyl)benzo[b]furan to a significant extent. The produced 2-(2-heteroarylsulfanyl) vinyl radicals largely preferred to undergo intermolecular H-abstraction reaction rather than intramolecular 5-endo cyclization onto the heteroaryl moiety of the 2-sulfanyl substituent. The 2-[(2-thienylmethyl)sulfanyl]- and, especially, 2-[(2-furylmethyl)sulfanyl]vinyl radicals, besides H-abstraction, promptly underwent intramolecular B-exo cyclization to give spiro radicals that interestingly underwent beta-scission of their respective C-S and C-O bond resulting in ring cleavage of the original heteroaryl group. The 2-[(3-thienylmethyl)sulfanyl]vinyl radicals did not exhibit any similar B-exo cyclization, but did undergo a 6-endo cyclization to a very slight extent.