3,3′-ditrifluoromethyldiphenyl sulfide | 1580-30-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3,3′-ditrifluoromethyldiphenyl sulfide
• 英文别名: bis(3-(trifluoromethyl)phenyl)sulfane；bis(3-trifluoromethylphenyl)sulfane；1,1'-thiobis[3-(trifluoro-methyl) benzene]；3,3'-bis(trifluoromethyl)diphenyl sulfide；1,1'-thio-bis(3-trifluoromethyl)benzene；3,3'-Bis-trifluormethyl-diphenylsulfid；Di(m-trifluoromethylphenyl) sulfide；1-(trifluoromethyl)-3-[3-(trifluoromethyl)phenyl]sulfanylbenzene
• CAS: 1580-30-9
• 化学式: C₁₄H₈F₆S
• 分子量: 322.274
• InChiKey: RLMQWRRODRPLSJ-UHFFFAOYSA-N

物化性质

• 熔点：
  65-66 °C(Solv: ethanol (64-17-5))
• 沸点：
  321.9±42.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3,3′-ditrifluoromethyldiphenyl sulfide 在 2-(三甲基硅)苯基三氟甲烷磺酸盐 、 间氯过氧苯甲酸 、 cesium fluoride 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 72.0h， 生成 3,3’-双(三氟甲基)-1,1’-联苯
  参考文献：
  名称：

  苯炔对二芳基（杂芳基）亚砜的脱硫

  摘要：

  已经证明了两个能够进行苯并炔的脱硫反应，它们分别将二芳基亚砜和杂芳基亚砜转化为联芳基和脱硫的杂芳烃。接近联芳基的反应可耐受各种官能团，例如卤化物，假卤化物和羰基。机理研究表明，两个反应均通过共同的组装过程进行，但生成的四芳基（杂芳基）硫烷的分解程度不同。

  DOI：

  10.1021/acs.orglett.9b01144
• 作为产物：
  描述：

  三氟甲苯 在 五氟化锑 、 氟磺酸 作用下， 以 1,1,2-三氯三氟乙烷（CFC-113） 为溶剂， 反应 31.5h， 生成 3,3′-ditrifluoromethyldiphenyl sulfide
  参考文献：
  名称：

  Reaction of simple arenes with FSO3H.cntdot.SbF5/SO2: one-pot synthesis of aromatic sulfoxides. Mechanistic aspects and synthetic utility

  摘要：

  In a simple one-pot reaction, mono-, di-, tri-, and polyalkylbenzenes, isomeric alkylhalobenzenes, and fluoro-, (trifluoromethyl)-, and 1,3,5-trifluorobenzene were converted to their corresponding diaryl sulfoxides with FSO3H.SbF5 (1:1) (magic acid)/SO2. Dependency of the yields on the acidity (H0) and the arene structure was demonstrated. Reduction of the formed sulfoxide was also observed as a minor pathway to give diaryl sulfide. The reduction is superacid-catalyzed, and protonated sulfoxides are the key intermediates en route to sulfides. Protonation of several functionalized diaryl sulfoxides was also studied in magic acid/SO2 under stable ion conditions. Unlike the parent diphenyl sulfoxide, which is S-protonated, alkyl-, fluoro-, and trifluoromethyl-substituted diaryl sulfoxides O-protonate to give long-lived sulfoxonium ions. The proposed mechanism for the arene/superacid/SO2 system involves sulfination of the arenium ions, O-protonation of the resulting sulfinic acid, dehydration of the oxonium ion ''ArSO+'' and arylation. In the absence of SO2, the fluorosulfonation, ionization, arylation path becomes dominant. The scope of the reaction is sufficiently broad to be synthetically useful. The methodology is also applicable to unsymmetrical (mixed) diaryl sulfoxides.

  DOI：

  10.1021/jo00005a037

文献信息

• Trisaminomethane–cobalt complex supported on Fe ₃ O ₄ magnetic nanoparticles as an efficient recoverable nanocatalyst for oxidation of sulfides and C–S coupling reactions
  作者：Muhammad Aqeel Ashraf、Zhenling Liu、Wan‐Xi Peng

  DOI：10.1002/aoc.5260

  日期：2020.1

  In this work, trisaminomethane–cobalt complex immobilized onto the surface of Fe3O4 magnetic nanoparticles was successfully prepared via a simple and inexpensive procedure. The prepared nanocatalyst was considered a robust and clean nanoreactor catalyst for the oxidation and synthesis of sulfides under green conditions. This ecofriendly heterogeneous catalyst was characterized by Fourier transform

  在这项工作中，三氨基甲烷-钴络合物固定在Fe 3 O 4的表面上通过简单且廉价的程序成功制备了磁性纳米颗粒。所制备的纳米催化剂被认为是在绿色条件下用于氧化和合成硫化物的坚固，清洁的纳米反应器催化剂。这种环保型非均相催化剂的特征在于傅立叶变换红外光谱，X射线衍射法，能量色散X射线光谱法，电感耦合等离子体原子发射光谱法，热重分析，振动样品磁力分析法，X射线作图，扫描电子显微镜和透射电子显微镜技术。使用绿色介质，易于分离和后处理，纳米催化剂的优异可重复使用性以及较短的反应时间是该方法的一些突出优点。
• [EN] GLUCOSE-SENSITIVE ALBUMIN-BINDING DERIVATIVES<br/>[FR] DÉRIVÉS DE LIAISON À L'ALBUMINE SENSIBLES AU GLUCOSE
  申请人：NOVO NORDISK AS

  公开号：WO2019092125A1

  公开（公告）日：2019-05-16

  This invention relates to glucose-sensitive albumin-binding diboron conjugates. More particularly the invention provides novel diboron compounds, and in particular diboronate or diboroxole compounds, useful as intermediate compounds for the synthesis of diboron conjugates. The diboron compounds are characterized by formula (I), which is: R1-X-R2, and wherein "X" is a mono- to multiatomic linker and where R1 and R2, which may be identical or different, each represents a group of Formula (lla) or (IIb) Also described are diboron conjugates represented by the general Formula (I'), which is: R1'-X'-R2', in which either the moeities R1' or R2' or X' carry a drug that is covalently attached to the diboron compound.

  这项发明涉及葡萄糖敏感的白蛋白结合二硼共轭物。更具体地，该发明提供了新颖的二硼化合物，特别是二硼酸酯或二硼醇化合物，可用作合成二硼共轭物的中间化合物。这些二硼化合物的特征是式(I)，即：R1-X-R2，其中“X”是单原子到多原子的连接物，而R1和R2，可以相同也可以不同，每个代表式(IIa)或(IIb)的基团。还描述了由一般式(I')表示的二硼共轭物，即：R1'-X'-R2'，其中R1'或R2'或X'中的任一部分携带与二硼化合物共价连接的药物。
• The first report on the preparation of peptide nanofibers decorated with zirconium oxide nanoparticles applied as versatile catalyst for the amination of aryl halides and synthesis of biaryl and symmetrical sulfides
  作者：Arash Ghorbani-Choghamarani、Zahra Taherinia

  DOI：10.1039/c7nj00628d

  日期：——

  zirconium oxide nanoparticles for the first time as a novel, non-toxic, inexpensive and recyclable catalyst for the amination of aryl halides and synthesis of biaryl and symmetrical sulfides (via reaction of aryl halides with S8 or 2-thiobarbituric acid as sulfur transfer reagents). The structure of the catalyst was studied by Fourier transform infrared spectroscopy (FT-IR), scanning electron microscopy

  我们首次报道了用氧化锆纳米粒子修饰的肽纳米纤维的制备，这是一种新颖，无毒，廉价且可回收的催化剂，用于芳基卤化物的胺化以及联芳基和对称硫化物的合成（通过芳基卤化物与S的反应）8或2-硫代巴比妥酸作为硫转移试剂）。通过傅里叶变换红外光谱（FT-IR），扫描电子显微镜（SEM），热重分析（TGA），原子吸收光谱（AAS），紫外可见吸收光谱和荧光光谱研究了催化剂的结构。
• A simple, efficient and recyclable catalytic system for carbon–sulfur coupling of aryl halides with thioacetamide
  作者：Mingzhong Cai、Ruiya Yao、Lin Chen、Hong Zhao

  DOI：10.1016/j.molcata.2014.08.010

  日期：2014.12

  The carbon–sulfur coupling reaction of aryl halides with thioacetamide using an MCM-41-immobilized bidentate nitrogen copper(I) complex [MCM-41-2N-CuI] as an efficient heterogeneous catalyst is described. Developed catalytic system is found to be effective for the coupling reaction of aryl halides with thioacetamide providing moderate to high yield of diaryl sulfides. This heterogeneous copper catalyst

  描述了使用MCM-41固定的双齿氮铜（I）络合物[MCM-41-2N-CuI]作为有效的多相催化剂，芳基卤化物与硫代乙酰胺的碳-硫偶联反应。发现开发的催化体系对于芳基卤化物与硫代乙酰胺的偶联反应有效，提供中等至高产率的二芳基硫化物。这种多相铜催化剂显示出比CuI更高的活性，可以通过简单过滤反应溶液进行回收，并且可以重复使用至少10次，而活性不会降低。
• Synthesis of sulfides via reaction of aryl/alkyl halides with S₈ as a sulfur-transfer reagent catalyzed by Fe₃O₄-magnetic-nanoparticles-supported L-Histidine-Ni(II)
  作者：Gouhar Azadi、Zahra Taherinia、Ali Naghipour、Arash Ghorbani-Choghamarani

  DOI：10.1080/17415993.2017.1287265

  日期：2017.5.4

  ABSTRACT One-pot synthesis of symmetrical diaryl/alkyl sulfides in high yields from the reaction between aryl/alkyl halides and S8 can be carried out in a short period, using Fe3O4@SiO2@His@Ni(II) as a reusable catalyst. The present approach offers the advantages of a clean reaction, simple methodology and high efficiency, and avoids the use of a toxic catalyst. GRAPHICAL ABSTRACT

  摘要 使用 Fe3O4@SiO2@His@Ni(II) 作为可重复使用的催化剂，芳基/烷基卤化物与 S8 之间的反应可以高产率地一锅法合成对称的二芳基/烷基硫化物。本方法具有反应清洁、方法简单和效率高的优点，并且避免了使用有毒催化剂。图形概要