Phenyl-2,5-dimethyl-phenyl-sulfid | 16704-45-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: Phenyl-2,5-dimethyl-phenyl-sulfid
• 英文别名: 1,4-Dimethyl-2-phenylsulfanylbenzene
• CAS: 16704-45-3
• 化学式: C₁₄H₁₄S
• 分子量: 214.331
• InChiKey: FPTWOARARXATQR-UHFFFAOYSA-N

物化性质

• 沸点：
  171 °C(Press: 11 Torr)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  15
• 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：
  1

反应信息

• 作为反应物：
  描述：

  Phenyl-2,5-dimethyl-phenyl-sulfid 在 双氧水 作用下， 以 溶剂黄146 为溶剂， 生成 Phenyl-2,5-dimethyl-phenyl-sulfoxid
  参考文献：
  名称：

  Syntheses and reactions of triarylsulfonium halides

  摘要：

  DOI：

  10.1021/jo01271a012
• 作为产物：
  描述：

  在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以29.3 mg的产率得到Phenyl-2,5-dimethyl-phenyl-sulfid
  参考文献：
  名称：

  使用亚砜的芳烃的无金属CH硫芳基化反应：直接的，一般的二芳基硫醚合成

  摘要：

  使用甲基亚砜的芳烃和杂芳烃的无金属CH硫芳基化反应，构成了合成高价值二芳基硫醚的一般无金属方案。芳烃和杂芳烃与...的偶联

  DOI：

  10.1039/c6cc07627k

文献信息

• Regiospecific Reductive Elimination from Diaryliodonium Salts
  作者：Bijia Wang、Joseph W. Graskemper、Linlin Qin、Stephen G. DiMagno

  DOI：10.1002/anie.201000695

  日期：2010.6.1

  Out‐of‐plane steric bulk furnished by a cyclophane substituent on iodine(III) strongly destabilizes the transition state in the reductive elimination from diaryliodonium salts and leads to regiochemical control (dubbed SECURE), as is demonstrated by computational and experimental studies. This approach should be general for high‐valent main‐group and transition metal ions. X=N3, OAc, PhO, CF3CH2O,

  正如计算和实验研究所证明的那样，碘（III）上的环芳取代基提供的面外空间体积强烈地破坏了二芳基碘鎓盐还原消除过程中的过渡态的稳定性，并导致区域化学控制（称为“安全”）。这种方法对于高价主族和过渡金属离子应该是通用的。 X=N 3 、OAc、PhO、CF 3 CH 2 O、SCN、PhS。
• AlCl3-Mediated Aromatic Phenylthiation with N-Phenylthiophthalimide.
  作者：Satoshi SUWA、Takeshi SAKAMOTO、Yasuo KIKUGAWA

  DOI：10.1248/cpb.47.980

  日期：——

  N-Phenylthiophthalimide reacts with AlCl3 or TiCl4 in areanes to give phenylthiated arenes alone via a phenylsulfenium ion intermediate, modified neglect of diatomic overlap (MNDO) molecular orbital calculations of which revealed that the positive charge preferentially populates the sulfur atom rather than the phenyl group in the phenylsulfenium ion.

  N-苯硫基邻苯二甲酰亚胺与烷烃中的 AlCl3 或 TiCl4 反应，通过苯硫离子中间体生成苯硫基烷烃，其修正的忽略二原子重叠（MNDO）分子轨道计算显示，正电荷优先填充苯硫离子中的硫原子而不是苯基。
• Process for preparing polyarylene thioethers
  申请人：SEISAN KAIHATSU KAGAKU KENKYUSHO

  公开号：EP0440106A2

  公开（公告）日：1991-08-07

  Polyarylene thioethers are easily prepared by an oxidative polymerization of an aromatic compound of the formula (I) wherein R¹, R², R³ and R⁴ are each independently a hydrogen atom, a halogen atom, a lower alkyl group or a lower alkoxy group, and Y is a hydrogen atom or a group of the formula (II) wherein R⁵, R⁶, R⁷ and R⁸ are each independently a hydrogen atom, a halogen atom, a lower alkyl group or a lower alkoxy group and X is -O-, -S-, a methylene group or an ethylene group with a sulfidizing agent in the presence of an acid and an oxidizing agent, or in the presence of an acid, a catalyst for oxidative polymerization and oxygen, or in the presence of a Friedel-Crafts catalyst.

  通过式 (I) 的芳香族化合物的氧化聚合可轻松制备聚芳硫醚，式 (I) 中 R¹、R²、R³ 和 R⁴ 各自独立地为氢原子、卤素原子、低级烷基或低级烷氧基，Y 为氢原子或式 (II) 的基团，式 (II) 中 R⁵、R⁶、 R⁵、R⁶、R⁷ 和 R⁸ 各自独立地为氢原子、卤素原子、低级烷基或低级烷氧基，X 为-O-、-S-、亚甲基或亚乙基，在有酸和氧化剂存在下，或在有酸、氧化聚合催化剂和氧存在下，或在有 Friedel-Crafts 催化剂存在下，加入硫化剂。
• Application of hydrazone ligands in Chan−Lam coupling of arylboronic acids and thiols
  作者：Legen Hu、Jiaquan Wang、Kelun Cui、Lin Zheng、Chunyin Zhu

  DOI：10.1016/j.tet.2024.133945

  日期：2024.4

  A Cu/hydrazone catalysis has been applied in the oxidative coupling of arylboronic acids and aromatic thiols for the synthesis of asymmetric diaryl sulfides. The reaction features mild conditions and readily available hydrazone ligand. It works for a wide range of arylboronic acids and thiols with good to excellent yields, exhibiting great potential of such hydrazone ligands in organic synthesis.

  Cu/腙催化已应用于芳基硼酸和芳香硫醇的氧化偶联，以合成不对称二芳基硫醚。该反应条件温和，腙配体易于获得。它适用于多种芳基硼酸和硫醇，具有良好至优异的产率，展示了此类腙配体在有机合成中的巨大潜力。
• Silver catalyzed C–C and C–S coupling of aryl halides and thiols with boronic acids
  作者：Rima Das、Debashis Chakraborty

  DOI：10.1016/j.tetlet.2012.09.127

  日期：2012.12

  An efficient Ag(I) catalyzed carbon-carbon and carbon-sulfur bond formation reaction of aryl halides and thiols with boronic acids has been demonstrated. Using this protocol, substrates with a wide range of functional group including electron-rich, and electron deficient substituents have been explored. These reactions are particularly useful to prepare symmetrical and unsymmetrical biphenyls and thioethers. These products were isolated in high yield. (c) 2012 Elsevier Ltd. All rights reserved.