1,4-di(p-tolylthio)butane | 94265-88-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1,4-di(p-tolylthio)butane
• 英文别名: 1.4-Di-p-tolylmercapto-butan；1,4-bis-p-tolylsulfanyl-butane；1,4-Bis-p-tolylmercapto-butan；1,1'-(Butane-1,4-diyldisulfanediyl)bis(4-methylbenzene)；1-methyl-4-[4-(4-methylphenyl)sulfanylbutylsulfanyl]benzene
• CAS: 94265-88-0
• 化学式: C₁₈H₂₂S₂
• 分子量: 302.505
• InChiKey: ZHBZUMMXMKJGCU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  50.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,4-di(p-tolylthio)butane 在 N-氯代丁二酰亚胺 、 间氯过氧苯甲酸 作用下， 以 四氯化碳 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 1,4-dichloro-1,4-di(p-tolylsulfinyl)butane
  参考文献：
  名称：

  A synthesis of diketones from carbonyl compounds and α,ω-dichloro-α,ω-disulfinylalkanes with two carbon–carbon bond-formation via bis-sulfinyloxiranes

  摘要：

  Bis-sulfinyloxiranes were synthesized in two steps from carbonyl compounds and alpha,omega-dichloro-alpha,omega-disulfinylalkanes, which were synthesized from alpha,omega-dibromoalkanes in three steps, in good yields. Treatment of the bis-sulfinyloxiranes with sodium benzenethiolate and piperidine gave alpha,alpha'-di(phenylthio) diketones and alpha,alpha'-diamino diketones, respectively, in high yields. From these products, some kinds of diketones were synthesized in good to high yields. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00352-6
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 以 二氯甲烷 、 乙腈 为溶剂， 反应 4.0h， 以77%的产率得到1,4-di(p-tolylthio)butane
  参考文献：
  名称：

  Abd-El-Aziz, Alaa S.; Epp, Karen M.; Lei, Yun, Journal of Chemical Research, Miniprint, 1995, # 5, p. 1252 - 1286

  摘要：

  DOI：

文献信息

• Copper-catalyzed visible-light-induced ring-opening carbonylation of sulfonium salts
  作者：Youcan Zhang、Zhi-Peng Bao、Chang-Sheng Kuai、Xiao-Feng Wu

  DOI：10.1016/j.jcat.2023.06.039

  日期：2023.10

  strategy for the synthesis of sulfur-containing carboxylic acid derivatives through copper/visible light catalyzed ring-opening carbonylation of sulfonium salts. The protocol employs photoredox to promote the selective cleavage of sulfonium salts C(sp3)-S bond, while performing sequential functionalization to form vicinal C–C and C-X (X = O or N) bonds in the presence of carbon monoxide and nucleophiles

  在此，我们开发了一种直接有效的策略，通过铜/可见光催化锍盐的开环羰基化合成含硫羧酸衍生物。该方案采用光氧化还原来促进锍盐 C(sp3)-S 键的选择性裂解，同时在一氧化碳和亲核试剂存在下进行顺序功能化以形成邻位 C-C 和 CX（X = O 或 N）键。多种底物成功转化为所需的羰基化产物，产率中等至良好，具有良好的官能团耐受性和优异的化学选择性。重要的是，这种方法可以很容易地扩展到生物活性分子的后期修饰。
• Marvel; Chambers, Journal of the American Chemical Society, 1948, vol. 70, p. 997
  作者：Marvel、Chambers

  DOI：——

  日期：——
• 715. Elimination–addition. Part I. Displacement of sulphonyl groups from diarylsulphonylalkanes
  作者：A. T. Kader、C. J. M. Stirling

  DOI：10.1039/jr9620003686

  日期：——
• Abd-El-Aziz, Alaa S.; Epp, Karen M.; Lei, Yun, Journal of Chemical Research, Miniprint, 1995, # 5, p. 1252 - 1286
  作者：Abd-El-Aziz, Alaa S.、Epp, Karen M.、Lei, Yun、Kotowich, Steven

  DOI：——

  日期：——
• A synthesis of diketones from carbonyl compounds and α,ω-dichloro-α,ω-disulfinylalkanes with two carbon–carbon bond-formation via bis-sulfinyloxiranes
  作者：Tsuyoshi Satoh、Daisaku Taguchi、Aki Kurabayashi、Makiko Kanoto

  DOI：10.1016/s0040-4020(02)00352-6

  日期：2002.5

  Bis-sulfinyloxiranes were synthesized in two steps from carbonyl compounds and alpha,omega-dichloro-alpha,omega-disulfinylalkanes, which were synthesized from alpha,omega-dibromoalkanes in three steps, in good yields. Treatment of the bis-sulfinyloxiranes with sodium benzenethiolate and piperidine gave alpha,alpha'-di(phenylthio) diketones and alpha,alpha'-diamino diketones, respectively, in high yields. From these products, some kinds of diketones were synthesized in good to high yields. (C) 2002 Elsevier Science Ltd. All rights reserved.