benzhydryl(benzyl)sulfane | 6622-09-9

• 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: benzhydryl(benzyl)sulfane
• 英文别名: Benzhydryl-benzyl-sulfid；Benzyl diphenylmethyl sulfide；benzhydrylsulfanylmethylbenzene
• CAS: 6622-09-9
• 化学式: C₂₀H₁₈S
• 分子量: 290.429
• InChiKey: HEARSPZHWOTBRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  benzhydryl(benzyl)sulfane 在 碘 作用下， 以 二氯甲烷 为溶剂， 生成 二苄基二硫
  参考文献：
  名称：

  An efficient and chemoselective method for protection of thiols catalyzed by aluminumdodecatungstophosphate (AlPW12O40), as a highly water tolerant Lewis acid catalyst

  摘要：

  Protection of various thiols with diphenylmethanol was achieved in high yields at room temperature using catalytic amounts of AlPW12O40 in CH2Cl2. In the presence of this catalyst, protection of SH versus OH was achieved with high chemo-selectivity and yields. The catalyst can be easily recovered and reused. Deprotection of DPM thioethers was also achieved using molecular iodine at reflux in CH2Cl2 in high yields. (c) 2005 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2005.02.071
• 作为产物：
  描述：

  苯甲醛 在 对甲苯磺酸一水合物 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 5.0h， 生成 benzhydryl(benzyl)sulfane
  参考文献：
  名称：

  Electrochemical desulfurative formation of C–N bonds through selective activation of inert C(sp³)–S bonds

  摘要：

  通过选择性活化烷基硫醚的惰性 C(sp3)-S 键来构建 C-N 键的高效无金属电催化脱硫策略。

  DOI：

  10.1039/d4cc00142g

文献信息

• Waste-Free Swift Synthesis of Symmetrical and Unsymmetrical Diarylmethyl Thioethers from Diaryl Carbinols
  作者：Rama Peddinti、Pallavi Singh

  DOI：10.1055/s-0036-1589022

  日期：2017.8

  to synthesize symmetrical and unsymmetrical diarylmethyl thioethers from diaryl carbinols and thiols in good to quantitative yields is reported. The thiol scope included alkyl and aryl thiols bearing electron-donating and electron-withdrawing groups. Short reaction time, high atom economy, inexpensive activator, free from workup and aryl halides, and gram-scale synthesis are the significant features

  摘要 报导了一种无浪费且快速的方案，可以从二芳基甲醇和硫醇以良好的定量收率合成对称和不对称的二芳基甲基硫醚。硫醇范围包括带有给电子基团和吸电子基团的烷基和芳基硫醇。短反应时间，高原子经济性，廉价的活化剂，免于后处理和芳基卤化物以及克级合成是新协议的重要特征。 报导了一种无浪费且快速的方案，可以从二芳基甲醇和硫醇以良好的定量收率合成对称和不对称的二芳基甲基硫醚。硫醇范围包括带有给电子基团和吸电子基团的烷基和芳基硫醇。短反应时间，高原子经济性，廉价的活化剂，免于后处理和芳基卤化物以及克级合成是新协议的重要特征。
• Selective synthesis of thioethers in the presence of a transition-metal-free solid Lewis acid
  作者：Federica Santoro、Matteo Mariani、Federica Zaccheria、Rinaldo Psaro、Nicoletta Ravasio

  DOI：10.3762/bjoc.12.259

  日期：——

  The synthesis of thioethers starting from alcohols and thiols in the presence of amorphous solid acid catalysts is reported. A silica alumina catalyst with a very low content in alumina gave excellent results in terms of both activity and selectivity also under solvent-free conditions. The reaction rate follows the electron density of the carbinol atom in the substrate alcohol and yields up to 99%

  据报道在无定形固体酸催化剂存在下由醇和硫醇开始的硫醚的合成。氧化铝含量极低的二氧化硅氧化铝催化剂在无溶剂条件下的活性和选择性方面均获得了优异的结果。反应速率遵循底物醇中甲醇原子的电子密度，产率高达99％，可以在温和的反应条件下获得多种底物。
• Tritylium assisted iodine catalysis for the synthesis of unsymmetrical triarylmethanes
  作者：Thibaut Courant、Marine Lombard、Dina V. Boyarskaya、Luc Neuville、Géraldine Masson

  DOI：10.1039/d0ob01502d

  日期：——

  The combined Lewis acid catalytic system, generated from molecular iodine and tritylium tetrafluoroborate effectively catalyzed the Friedel–Crafts (FC) arylation of diarylmethyl sulfides providing an efficient access to various unsymmetrical triarylmethanes. The addition of tritylium and iodine created a more active catalytic system to promote the cleavage of sulfidic C–S bonds.

  由分子碘和四氟硼酸三苯甲基酯生成的组合路易斯酸催化体系有效地催化二芳基甲基硫醚的傅克（FC）芳基化，从而有效地获得各种不对称三芳基甲烷。三苯甲基和碘的添加创造了一个更活跃的催化体系，以促进硫化 C-S 键的断裂。
• Chemistry of aliphatic disulfides—XIII
  作者：R.G. Hiskey、M.A. Harpold

  DOI：10.1016/s0040-4020(01)97902-5

  日期：1967.1

  Conditions have been devised for the oxidation of S-benzhydryl thioethers with thiocyanogen. The procedure involves the use of a trifluoroacetic acid-acetic acid solvent. These conditions do not effect a disulfide bond present in the substrate.

  已经设计了用于用硫氰酸根氧化S-苯甲酰基硫醚的条件。该过程涉及使用三氟乙酸-乙酸溶剂。这些条件不影响基材中存在的二硫键。
• Visible-Light-Triggered C–C and C–N Bond Formation by C–S Bond Cleavage of Benzylic Thioethers
  作者：Matteo Lanzi、Jérémy Merad、Dina V. Boyarskaya、Giovanni Maestri、Clémence Allain、Géraldine Masson

  DOI：10.1021/acs.orglett.8b02196

  日期：2018.9.7

  The cleavage of sulfidic C–S bonds under visible-light irradiation was harnessed to generate carbocations under neutral conditions and synthesize valuable di- and triarylalkanes as well as benzyl amines. To this end, photoredox catalysis and direct photoinduced C–S bond cleavage are used as complementary approaches and participate in the versatility of the general strategy. Extensive mechanistic studies

  利用中性条件下的硫化碳键在硫的裂解下可生成碳正离子，并合成有价值的二芳基和三芳基烷烃以及苄基胺。为此，光氧化还原催化和直接光诱导的C–S键断裂被用作补充方法，并参与了通用策略的多功能性。广泛的机理研究表明，在这些不同的反应中，反应机理的多样性。