4-nitrophenyl[bis(benzylthio)]methane | 21299-21-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-nitrophenyl[bis(benzylthio)]methane
• 英文别名: Dibenzylthioacetal von p-Nitrobenzaldehyd；α,α-Bis-benzylthio-p-nitrotoluol；4-nitro-benzaldehyde dibenzyldithioacetal；4-Nitro-ω.ω-bis-benzylthio-toluol；4-Nitro-benzaldehyd-dibenzylmercaptal；4-Nitro-benzal-bis-benzylsulfid；1-[Bis(benzylsulfanyl)methyl]-4-nitrobenzene
• CAS: 21299-21-8
• 化学式: C₂₁H₁₉NO₂S₂
• 分子量: 381.519
• InChiKey: CCRUNYVIZSABGB-UHFFFAOYSA-N

物化性质

• 沸点：
  531.9±50.0 °C(Predicted)
• 密度：
  1.268±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  96.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-nitrophenyl[bis(benzylthio)]methane 在 N-benzyl-DABCO tribromide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.1h， 以92%的产率得到对硝基苯甲醛
  参考文献：
  名称：

  N‐Benzyl‐DABCO‐tribromide as an efficient and mild reagent for deprotection of dithioacetals

  摘要：

  N-Benzyl-DABCO-ammonium tribromide was found to be an efficient and recyclable reagent for the deprotection of dithioacetals in dichloromethane/methanol at room temperature. The reaction can be performed cleanly, in short time, and in high yield.

  DOI：

  10.1080/00397910500498952
• 作为产物：
  描述：

  benzyl-(4-nitro-benzyl)-sulfoxide 在 溶剂黄146 作用下， 生成 4-nitrophenyl[bis(benzylthio)]methane
  参考文献：
  名称：

  .alpha.-Carbon-sulfur oxidation-reduction reactions of sulfoxides. The case of benzylic sulfoxides

  摘要：

  DOI：

  10.1021/jo01263a030

文献信息

• Direct Synthesis of Unsymmetrical Dithioacetals
  作者：Sabine Bognar、Manuel Gemmeren

  DOI：10.1002/chem.202004835

  日期：2021.3.12

  only discuss symmetrical dithioacetals. Examples of mixed dithioacetals are scarce and no general method for the selective synthesis of these compounds exists. Herein, a synthetically simple general one‐step protocol was developed for the synthesis of a broad range of unsymmetrical dithioacetals consisting of one aromatic and one aliphatic thiol moiety from the corresponding aldehyde/thiol mixture. The

  二硫缩醛是合成有机化学中经常使用的基序，近来作为结构基序出现在有前景的抗植物病原体抗病毒剂中的关注日益增加。但是，大多数现有报告仅讨论对称的二硫缩醛。混合的二硫缩醛的例子很少，并且不存在用于选择性合成这些化合物的通用方法。本文中，开发了一种合成简单的通用单步操作规程，用于从相应的醛/硫醇混合物中合成范围广泛的不对称二硫缩醛，该不对称二硫缩醛由一个芳族基团和一个脂肪族硫醇基组成。混合小号，小号乙缩醛的收率很高，并且可以容忍各种官能团。动力学控制实现了对不对称二硫缩醛的出色选择性。
• Ku, Bonchul; Oh, Dong Young, Synthetic Communications, 1989, vol. 19, # 3and4, p. 433 - 438
  作者：Ku, Bonchul、Oh, Dong Young

  DOI：——

  日期：——
• Silica-supported phosphorus pentoxide: a reusable catalyst for S,S-acetalization of carbonyl groups under ambient conditions
  作者：Hamid Reza Shaterian、Kobra Azizi、Nafiseh Fahimi

  DOI：10.1080/17415993.2010.542155

  日期：2011.2.1

  Phosphorus pentoxide supported on silica gel (P2O5/SiO2) efficiently acts as a highly active and reusable catalyst for cyclic and non-cyclic S,S-acetalization of a variety of carbonyl compounds under mild, solvent-free and ambient conditions. This method offers significant advantages such as high conversion, clean work-up, short reaction times and simplicity in operation.[GRAPHICS].
• N‐Benzyl‐DABCO‐tribromide as an efficient and mild reagent for deprotection of dithioacetals
  作者：Firouz Matloubi Moghaddam、Hassan Zali Boeini、Dordaneh Zargarani、Ghasem Rezanejad Bardajee

  DOI：10.1080/00397910500498952

  日期：2006.5

  N-Benzyl-DABCO-ammonium tribromide was found to be an efficient and recyclable reagent for the deprotection of dithioacetals in dichloromethane/methanol at room temperature. The reaction can be performed cleanly, in short time, and in high yield.
• Thioacetalization of aldehydes and ketones in SDS micelles
  作者：Kiumars Bahrami、Mohammad Mehdi Khodaei、Maryam Tajik、Mehdi Soheilizad

  DOI：10.1080/17415993.2011.608165

  日期：2011.10.1

  Aromatic aldehydes have been successfully converted into their corresponding dithioacetal, dithiolane and dithiane derivatives in excellent yields with thiol (benzyl thiol and thiophenol), 1,2-ethanedithiol and 1,3-propanedithiol using trichloroacetic acid in sodium dodecyl sulfate micelles. The same procedure is applicable to ketones, but they need more time to be converted into their thioacetals.[GRAPHICS].