1,2-bis(thiophen-2-ylmethyl)disulfane | 119784-44-0

• 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: 1,2-bis(thiophen-2-ylmethyl)disulfane
• 英文别名: Bis(2-thiophenemethyl) disulfide；2-[(thiophen-2-ylmethyldisulfanyl)methyl]thiophene
• CAS: 119784-44-0
• 化学式: C₁₀H₁₀S₄
• 分子量: 258.453
• InChiKey: WFMZJMLYKVJZAO-UHFFFAOYSA-N

物化性质

• 保留指数：
  2641

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  107
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,2-bis(thiophen-2-ylmethyl)disulfane 在 双氧水 、 溶剂黄146 作用下， 生成 [2]thienyl-methanethiosulfinic acid S-[2]thienylmethyl ester
  参考文献：
  名称：

  Kametani et al., Yakugaku Kenkyu, 1959, vol. 31, p. 125,131

  摘要：

  DOI：
• 作为产物：
  描述：

  2-噻吩甲基硫醇 在 三氟化硼乙醚 、 10-甲基-9-均三甲苯基吖啶高氯酸盐 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 9.0h， 生成 1,2-bis(thiophen-2-ylmethyl)disulfane
  参考文献：
  名称：

  三苯甲基保护的硫醇和醇的光催化裂解

  摘要：

  我们报告了在 pH 中性条件下三苯甲基硫醚或醚的可见光光催化裂解。该方法导致以中等到极好的收率形成相应的对称二硫化物和醇。该协议只需要添加合适的光催化剂和光使其与多种功能正交，包括酸不稳定保护基团。相同的条件可用于直接将三苯甲基保护的硫醇转化为不对称的二硫化物或硒硫化物，并在固相有机合成中裂解三苯甲基树脂。

  DOI：

  10.1055/a-1979-5933

文献信息

• Green Aerobic Oxidation of Thiols to Disulfides by Flavin–Iodine Coupled Organocatalysis
  作者：Hiroki Iida、Marina Oka、Ryo Kozako

  DOI：10.1055/a-1520-9916

  日期：2021.7

  molecular iodine successfully promoted the aerobic oxidation of thiols to disulfides under metal-free mild conditions. The activation of molecular oxygen occurred smoothly at room temperature through the transfer of electrons from the iodine catalyst to the biomimetic flavin catalyst, forming the basis for a green oxidative synthesis of disulfides from thiols.

  使用核黄素衍生的有机催化剂和分子碘的耦合催化成功地促进了硫醇在无金属温和条件下有氧氧化成二硫化物。通过将电子从碘催化剂转移到仿生黄素催化剂，分子氧的活化在室温下顺利发生，形成了硫醇绿色氧化合成二硫化物的基础。
• Thermal conversion of primary alcohols to disulfides<i>via</i>xanthate intermediates: an extension to the Chugaev elimination
  作者：Wei He、Yong Ding、Jianzhuo Tu、Chuqiang Que、Zhanhui Yang、Jiaxi Xu

  DOI：10.1039/c8ob00024g

  日期：——

  Primary alcohols are converted into dialkyl disulfides via heating in situ generated O-alkyl S-difluoro(ethoxycarbonyl)methyl xanthates from ethyl bromodifluoroacetate and potassium xanthates, prepared from primary alcohols and carbon disulfide in the presence of KOH. The reaction mechanism is suggested as an alkyl C[1,3] shift followed by a radical mechanism. This extends to the Chugaev elimination

  通过在KOH存在下，由伯二氟乙酸乙酯和黄原酸钾原位加热生成的O-烷基S-二氟（乙氧基羰基）甲基黄原酸酯，将伯醇转化为二烷基二硫化物，所述原酸由溴二氟乙酸乙酯和黄原酸钾制备。建议的反应机理为烷基的C [1,3]转移，其后为自由基机理。这扩展到楚格耶夫消除法，产生烯烃。当前的研究提供了从可商购获得的伯烷醇中容易获得二烷基二硫化物的途径。
• 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.
• Generation of Thiols by Biotransformation of Cysteine−Aldehyde Conjugates with Baker's Yeast
  作者：Tuong Huynh-Ba、Walter Matthey-Doret、Laurent B. Fay、Rachid Bel Rhlid

  DOI：10.1021/jf026198j

  日期：2003.6.1

  Baker's yeast was shown to catalyze the transformation of cysteine-furfural conjugate into 2-furfurylthiol. The biotransformation's yield and kinetics were influenced by the reaction parameters such as pH, incubation mode (aerobic and anaerobic), and substrate concentration. 2-Furfurylthiol wets obtained in an optimal 37% yield when cysteine-furfural conjugate at a 20 mM concentration wets anaerobically incubated with whole cell baker's yeast at pH 8.0 and 30 degreesC. Similarly to 2-furfurylthiol, 5-methyl-2-furfurylthiol (11%), benzylthiol (8%), 2-thiophenemethanethiol (22%), 3-methyl-2-thiophenemethanethiol (3%), and 2-pyrrolemethanethiol (6%) were obtained from the corresponding cysteine-aldehyde conjugates by incubation with baker's yeast. This work indicates the versatile bioconversion capacity of baker's yeast for the generation of thiols from cysteine-alclehyde conjugates. Thanks to its food-grade character, baker's yeast provides a biochemical tool to produce thiols, which can be used as flavorings in foods and beverages.
• Pseudo Five-Component Synthesis of 3-(Hetero)arylmethyl-2,5-di(hetero)-aryl-Substituted Thiophenes via Sonogashira–Glaser Cyclization Sequence
  作者：Thomas Müller、Fabian Klukas、Jörg Perkampus、Dominik Urselmann

  DOI：10.1055/s-0034-1379074

  日期：——

  The Sonogashira-Glaser sequence combined with a microwave-assisted cyclization is a powerful tool to synthesize unsymmetrically substituted conjugated thiophenes. A variety of 3-(hetero)arylmethyl-2,5-di(hetero)aryl-substituted thiophenes could be synthesized in moderate to excellent yields using a single Pd/Cu catalyst system. The presented method is strikingly simple to perform using commercially available starting materials. The obtained trisubstituted oligothiophene derivatives are interesting molecules for materials science.