Furan-3-methanethiol | 108499-25-8

• 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: Furan-3-methanethiol
• 英文别名: 3-Furylmethanethiol；3-Furanmethanethiol；furan-3-ylmethanethiol
• CAS: 108499-25-8
• 化学式: C₅H₆OS
• 分子量: 114.168
• InChiKey: QVJBJBWGSWLPQL-UHFFFAOYSA-N

物化性质

• 沸点：
  156.2±15.0 °C(Predicted)
• 密度：
  1.112±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 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：
  14.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Furan-3-methanethiol 在 二叔丁基过氧化物 、 potassium ethoxide 作用下， 以 乙醇 为溶剂， 生成 Furan-3-thioaldehyde radical anion
  参考文献：
  名称：

  Rotational conformers of furan- and thiophenethioaldehyde anion radicals

  摘要：

  The radical anions of the four isomeric furan and thiophene thioaldehydes have been obtained by photolysis, in an alkaline medium, of the corresponding thiols in the presence of di-tert-butyl peroxide. The same reaction also yields the four corresponding aldehyde radical anions, starting from the appropriate alcohols. The ESR spectra show that in most cases the two rotational conformers (E and Z) are present at the equilibrium. By means of appropriate methyl-substituted derivatives it has been possible to assign the structure of the two conformers. In the case of the 2-furan and 2-thiophene aldehyde anion radicals it has been also found that the conformational preference is the same as that exhibited by the corresponding molecules.

  DOI：

  10.1021/jo00022a023
• 作为产物：
  描述：

  3-呋喃甲醇 在 硫脲 作用下， 生成 Furan-3-methanethiol
  参考文献：
  名称：

  Rotational conformers of furan- and thiophenethioaldehyde anion radicals

  摘要：

  The radical anions of the four isomeric furan and thiophene thioaldehydes have been obtained by photolysis, in an alkaline medium, of the corresponding thiols in the presence of di-tert-butyl peroxide. The same reaction also yields the four corresponding aldehyde radical anions, starting from the appropriate alcohols. The ESR spectra show that in most cases the two rotational conformers (E and Z) are present at the equilibrium. By means of appropriate methyl-substituted derivatives it has been possible to assign the structure of the two conformers. In the case of the 2-furan and 2-thiophene aldehyde anion radicals it has been also found that the conformational preference is the same as that exhibited by the corresponding molecules.

  DOI：

  10.1021/jo00022a023

文献信息

• Fe-Catalyzed Thioesterification of Carboxylic Esters
  作者：Silja Magens、Bernd Plietker

  DOI：10.1002/chem.201101073

  日期：2011.8.1

  shelf‐stable aryl esters and thiols, a variety of carboxylic acid esters were transformed into the corresponding thioesters with no racemization of labile stereocenters (see scheme). The method was successfully applied in a native chemical‐ligation‐type peptide formation, which suggests that the thiol may act as a co‐catalyst for future 1,2‐additions of pronucleophiles to carboxylic esters.

  第二性质：从稳定的芳基酯和硫醇开始，各种羧酸酯被转化为相应的硫酯，而没有外消旋的立体中心（见方案）。该方法已成功地用于天然化学连接型肽的形成，这表明硫醇可能会作为亲核试剂将来向羧酸酯中添加1,2的助催化剂。
• Bifunctional iminophosphorane catalysed enantioselective sulfa-Michael addition of alkyl thiols to alkenyl benzimidazoles
  作者：Michele Formica、Geoffroy Sorin、Alistair J. M. Farley、Jesús Díaz、Robert S. Paton、Darren J. Dixon

  DOI：10.1039/c8sc01804a

  日期：——

  The first enantioselective sulfa-Michael addition of alkyl thiols to alkenyl benzimidazoles, enabled by a bifunctional iminophosphorane (BIMP) organocatalyst, is described. The iminophosphorane moiety of the catalyst provides the required basicity to deprotonate the thiol nucleophile while the chiral scaffold and H-bond donor control facial selectivity. The reaction is broad in scope with respect to

  描述了由双功能亚氨基正膦 (BIMP) 有机催化剂实现的烷基硫醇与烯基苯并咪唑的首次对映选择性磺胺-迈克尔加成。催化剂的亚氨基正膦部分提供了硫醇亲核试剂去质子化所需的碱性，而手性支架和氢键供体则控制面选择性。就硫醇和苯并咪唑反应伙伴而言，该反应范围很广，反应收率高达 98%，反应率为 96:4。
• A Novel Histamine 2(H2) Receptor Antagonist with Gastroprotective Activity. I. Synthesis and Pharmacological Evaluation of N-Phenoxypropylacetamide Derivatives with Thioether Function.
  作者：Yasuo SEKINE、Nobuhiko HIRAKAWA、Noriaki KASHIWABA、Hajime MATSUMOTO、Teruo KUTSUMA、Tetsuaki YAMAURA、Akihiro SEKINE

  DOI：10.1248/cpb.46.610

  日期：——

  N-(phenoxypropyl)acetamide derivatives with a thioether moiety and their sulfur-oxidized analogues were synthesized and evaluated for histamine H2-receptor antagonistic activity, Ca antagonistic activity and gastric anti-secretory activity in the lumen-perfuseed rat. Selected compounds were also tested for gastroprotective activity, which was expected to be based on Ca antagonistic activity. Structure-activity

  为了开发新型抗溃疡药，合成了一系列具有硫醚部分的N-（苯氧丙基）乙酰胺衍生物及其硫氧化类似物，并评估了其对组胺H2-受体的拮抗活性，对钙的拮抗活性和对胃的抑制作用。腔灌注大鼠体内的抗分泌活性。还测试了选择的化合物的胃保护活性，预期其基于Ca拮抗活性。讨论了构效关系。作为硫醚部分，发现-CH 2 -S（O）对-CH 2 -Ar（Ar；苯基或呋喃基）对于上述活性是最佳的。特别地，在大鼠模型中，N- [3-[（3-（哌啶子基甲基）苯氧基]丙基]乙酰胺与苄基亚磺酰基，苄基磺酰基，糠基亚磺酰基或糠基磺酰基显示出有效的胃保护活性。这些化合物是具有胃抗分泌和胃保护活性的新型抗溃疡药物的候选者。2-糠基亚磺酰基-N- [3-[（哌啶子基甲基）苯氧基]丙基]乙酰胺是测试化合物中最有效的，代号为FRG-8701。
• Synthesis of N-sulfenylimines via an electrochemical radical coupling of amines and thiols mediated by bromide ions
  作者：Qian Wang、Haibo Mei、Romana Pajkert、Gerd-Volker Röschenthaler、Jianlin Han

  DOI：10.1016/j.tet.2024.134133

  日期：2024.8

  electrochemical dehydrogenative coupling reaction between amines and thiols at room temperature has been developed, which includes the formation of imine intermediate and N–S bond as key steps enabling rapid synthesis of -sulfenylimines. The method successfully applies to a wide range of amines as well as structurally diverse thiols, exhibiting excellent functional group tolerance. The reaction also can be scaled

  开发了一种在室温下胺和硫醇之间的高效电化学脱氢偶联反应，其中包括亚胺中间体和N-S键的形成作为快速合成-硫基亚胺的关键步骤。该方法成功地适用于多种胺以及结构多样的硫醇，表现出优异的官能团耐受性。该反应还可以放大，为α-硫基亚胺提供了一种高效、绿色的方法。
• Del Zotto, Alessandro; Baratta, Walter; Rigo, Pierluigi, Journal of the Chemical Society. Perkin transactions I, 1999, # 21, p. 3079 - 3082
  作者：Del Zotto, Alessandro、Baratta, Walter、Rigo, Pierluigi

  DOI：——

  日期：——