((4-bromophenyl)methylene)bis(ethylsulfane) | 69895-02-9

• 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-bromophenyl)methylene)bis(ethylsulfane)
• 英文别名: 1-[Bis(ethylsulfanyl)methyl]-4-bromobenzene
• CAS: 69895-02-9
• 化学式: C₁₁H₁₅BrS₂
• 分子量: 291.276
• InChiKey: ULSAMUWRTFLFAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 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：

  ((4-bromophenyl)methylene)bis(ethylsulfane) 在 三甲基氯硅烷 、 sodium iodide 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 40.0h， 以92%的产率得到(4-bromobenzyl)(ethyl)sulfane
  参考文献：
  名称：

  氯三甲基硅烷和碘化钠：温和条件下苯甲酰二硫缩酮脱硫的显着无金属协会

  摘要：

  报道了一种新颖的无金属工艺，该工艺可对各种苄基二硫缩酮进行还原脱硫，从而以良好或优异的收率得到二芳基甲烷和苄基酯衍生物。在室温下，这种温和的还原过程仅需要在CH 2 Cl 2中使用TMSC1和NaI，并能耐受多种官能团。

  DOI：

  10.1002/adsc.201800437
• 作为产物：
  描述：

  对溴苯甲醛 、 乙硫醇 在 三聚氯氰 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以84%的产率得到((4-bromophenyl)methylene)bis(ethylsulfane)
  参考文献：
  名称：

  氰尿酰氯催化的硫代缩醛化用于硫代缩醛的有机催化合成

  摘要：

  图形摘要 使用氰尿酰氯作为有机催化剂，在各种硫醇和苯硫酚的存在下，芳香醛的硫缩醛化已经实现了广泛的多样性。

  DOI：

  10.1080/10426507.2015.1054934

文献信息

• Ethyl lactate mediated thioacetalization of aldehydes at ambient temperature
  作者：Jie-Ping Wan、Yanfeng Jing、Yunyun Liu

  DOI：10.1080/10426507.2016.1209504

  日期：2016.10.2

  GRAPHICAL ABSTRACT ABSTRACT Dithioacetalization reactions of aldehydes with thiols/thiophenols have been successfully achieved at room temperature by employing the green, bio-based ethyl lactate as the reaction medium. By means of this sustainable approach, a class of dithioacetals has been acquired with high diversity and efficiency.

  图形摘要摘要 醛与硫醇/苯硫酚的二硫代缩醛反应已在室温下通过采用绿色生物基乳酸乙酯作为反应介质成功实现。通过这种可持续的方法，已经获得了一类具有高度多样性和效率的二硫缩醛。
• 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].
• Hafnium Trifluoromethanesulfonate (Hafnium Triflate) as a Highly Efficient Catalyst for Chemoselective Thioacetalization and Transthioacetalization of Carbonyl Compounds
  作者：Yan-Chao Wu、Jieping Zhu

  DOI：10.1021/jo8021988

  日期：2008.12.5

  A range of carbonyl compounds including aliphatic and aromatic aldehydes and ketones were converted to the corresponding thioacetals in high yields in the presence of a catalytic amount of hafnium trifluoromethanesulfonate (0.1 mol %, room temperature), The mild conditions tolerated various sensitive functional and protecting groups and were racemization-free when applied to alpha-aminoaldehydes. Transacetalization and chemoselective thioacetalization of aromatic aldehydes in the presence of aliphatic aldehydes and ketones were also documented.
• Catalytic syntheses of γ-functionalized α-keto esters from thioacetals and N,O-acetals
  作者：Anke Krebs、Carsten Bolm

  DOI：10.1016/j.tet.2011.04.013

  日期：2011.6

  Ethyl 2-(trimethylsilyloxy)acrylic ester (1a) reacts with thioacetals providing the corresponding alpha-keto-gamma-thio esters in good to satisfactory yields. Whereas aminals do not react, N,O-acetals lead to gamma-amino-alpha-keto esters in good to excellent yields. All reactions proceed under mild reaction conditions, and no additional work up is required. Subsequent transformations of the obtained products to the corresponding alpha-oximes have been demonstrated. (C) 2011 Elsevier Ltd. All rights reserved.
• Chlorotrimethylsilane and Sodium Iodide: A Remarkable Metal-Free Association for the Desulfurization of Benzylic Dithioketals under Mild Conditions
  作者：Guangkuan Zhao、Ling-Zhi Yuan、Mouad Alami、Olivier Provot

  DOI：10.1002/adsc.201800437

  日期：2018.7.4

  A novel metal‐free process allowing the reductive desulfurization of various benzylic dithioketals to afford diarylmethane and benzylester derivatives with good to excellent yields is reported. At room temperature, this mild reduction process requires only the use of TMSCl and NaI in CH2Cl2 and tolerates a large variety of functional groups.

  报道了一种新颖的无金属工艺，该工艺可对各种苄基二硫缩酮进行还原脱硫，从而以良好或优异的收率得到二芳基甲烷和苄基酯衍生物。在室温下，这种温和的还原过程仅需要在CH 2 Cl 2中使用TMSC1和NaI，并能耐受多种官能团。