benzothien-2-yl disulfide | 19434-29-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: benzothien-2-yl disulfide
• 英文别名: 2-Benzothienyl disulfide；2,2'-dithiobisbenzothiazole；bis-benzo[b]thiophen-2-yl disulfide；Bis-benzo[b]thiophen-2-yl-disulfid；2-(1-Benzothiophen-2-yldisulfanyl)-1-benzothiophene
• CAS: 19434-29-8
• 化学式: C₁₆H₁₀S₄
• 分子量: 330.519
• InChiKey: STILJYSSDRQMAA-UHFFFAOYSA-N

物化性质

• 熔点：
  114.5-115 °C(Solv: benzene (71-43-2); ethanol (64-17-5))
• 沸点：
  497.9±20.0 °C(Predicted)
• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  4-叔丁基苯乙烯 、 benzothien-2-yl disulfide 、 苯甲亚胺酸乙酯 在 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 双三氟甲烷磺酰亚胺银盐 、 copper(II) acetate monohydrate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 12.0h， 以51%的产率得到(E)-2-(benzo[b]thiophen-2-yl)-6-(4-(tert-butyl)styryl)benzonitrile
  参考文献：
  名称：

  连续的 C-H 活化能够方便地传递多功能芳烃

  摘要：

  从丰富的原料中模块化构建多功能芳烃是合成化学的不懈追求，加速了药物和材料的发现。在此，使用多功能亚胺酸酯的多重 C-H 活化策略，实现了密集功能化的含硫芳烃分子库的便捷传递，从而能够简明地构建生物活性分子，如双苯萘酚。

  DOI：

  10.1039/d1cc03243g
• 作为产物：
  描述：

  benzothiophen-2-yllithium 在 乙醚 、 硝酸 、 sulfur 作用下， 生成 benzothien-2-yl disulfide
  参考文献：
  名称：

  Mitra et al., Journal Of Scientific and Industrial Research, 1957, vol. 16 B, p. 348,351

  摘要：

  DOI：

文献信息

• Mild and highly efficient method for the oxidation of sulfides and oxidative coupling of thiols catalyzed by Fe3O4@MCM-41@VO-SPATB as efficient and magnetically recoverable nanocatalyst
  作者：Mohsen Nikoorazm、Farshid Ghorbani、Arash Ghorbani-Choghamarani、Zahra Erfani

  DOI：10.1007/s13738-018-1536-3

  日期：2019.3

  functionalized magnetic nanoporous MCM-41(Fe3O4@MCM-41@VO-SPATB) as efficient and magnetically recoverable nanocatalyst for oxidation of sulfides into sulfoxides and oxidative coupling of thiols into disulfides using H2O2 as green oxidant is presented. This method provides much improved modification of oxidation reactions in terms of mild reaction conditions, short reaction time and good-to-excellent yields

  羰基钒配合物与固定在功能化磁性纳米多孔MCM-41（Fe 3 O 4 @ MCM-41 @ VO-SPATB）上的s-丙基-2-氨基苯甲硫酸酯配体的使用作为有效的和磁性可回收的纳米催化剂，用于将硫化物氧化为亚砜和介绍了使用H 2 O 2作为绿色氧化剂将硫醇氧化成二硫化物的方法。该方法在温和的反应条件，较短的反应时间和良好至优异的产物收率方面提供了改进的氧化反应修饰。该方法的另一个重要特征是能够将磁铁矿纳米催化剂重复使用几次而不会损失其催化活性。
• Addition of heteroaromatic thiols to electron-rich alkenes: a reversed hetero ene reaction
  作者：Pier Carlo Montevecchi、Maria Luisa Navacchia

  DOI：10.1021/jo00125a036

  日期：1995.10

  Benzothiophenethiol la reacted with styrene to give thiol 2a, which resulted from a ''reversed hetero ene reaction''. When the reaction was carried out in the presence of radical precursors, products deriving from radical addition to the styrene double bond of both thiols la and 2a were formed. The reaction of 1a with butyl vinyl ether (EVE) gave the alpha,beta-unsaturated dithioester 23a, deriving from the ''ene reaction product'' 22a through elimination of butanol. Similar behavior was exhibited by benzofuranthiol Ib, which reacted with styrene to give thiol 2b and with EVE to give the thionoester 23b. Both dithio- and thionoesters 23a,b were trapped as Diels-Alder adducts. In contrast, thiophenethiol Ic did not react with styrene and reacted with EVE to give an electrophilic 1:1 adduct. Ene reaction of thiols la,b occurred only with electron-rich olefins. In agreement, la did not react with hex-l-ene and methyl acrylate and reacted with dimethyl maleate to give a nucleophilic adduct.
• 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.
• NOVEL ORGANIC SEMICONDUCTIVE MATERIAL AND ELECTRONIC DEVICE USING THE SAME
  申请人：Ricoh Company Ltd.

  公开号：EP2457272A1

  公开（公告）日：2012-05-30
• US5869599A
  申请人：——

  公开号：US5869599A

  公开（公告）日：1999-02-09