2-Phenylsulfenyldimedon | 72117-61-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-Phenylsulfenyldimedon
• 英文别名: 5,5-Dimethyl-2-(phenylsulfanyl)-1,3-cyclohexanedione；5,5-dimethyl-2-phenylsulfanylcyclohexane-1,3-dione
• CAS: 72117-61-4
• 化学式: C₁₄H₁₆O₂S
• 分子量: 248.346
• InChiKey: RHFUXGNBGOUETF-UHFFFAOYSA-N

物化性质

• 熔点：
  116-119 °C
• 沸点：
  402.6±45.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  59.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Phenylsulfenyldimedon 以 乙腈 为溶剂， 以46%的产率得到2-Fluoro-5,5-dimethyl-2-(phenylthio)-1,3-cyclohexanedione
  参考文献：
  名称：

  Electrolytic Partial Fluorination of Organic Compounds. 17. Regiospecific Anodic Fluorination of Sulfides Bearing Electron-Withdrawing Substituents at the Position .alpha. to the Sulfur Atom

  摘要：

  Regiospecific monofluorination of various sulfides bearing electron-withdrawing substituents, cyano, ester, acyl, amino, and phosphonate groups,at their alpha-positions was successfully carried out by the anodic oxidation of the sulfides in Et(3)N . 3HF/MeCN using an undivided cell. Fluorine was introduced at the position alpha to the sulfur atom selectively. Fluorination of alpha-(phenylthio)-substituted cyclic carbonyl compounds was also successful. Furthermore, anodic alpha,alpha-difluorination of ethyl alpha-(phenylthio)acetate was also successfully carried out although a large amount of electricity was required.

  DOI：

  10.1021/jo00116a037
• 作为产物：
  描述：

  4-(苯基硫烷基)吗啉 以 甲苯 为溶剂， 生成 2-Phenylsulfenyldimedon
  参考文献：
  名称：

  Sulfur Ylides from Alkyl(aryl)-dialkylamino-succinimidosulfonium Chlorides¹

  摘要：

  DOI：

  10.1055/s-1976-24025

文献信息

• Continuous Flow Generation of Acylketene Intermediates via Nitrogen Extrusion
  作者：Harry R. Smallman、Guilherme A. Brancaglion、Julio C. Pastre、Duncan L. Browne

  DOI：10.1021/acs.joc.2c01486

  日期：2022.9.16

  of acylketene precursors through extrusion of nitrogen gas is reported. Key to the development of a suitable continuous protocol is the balance of reaction concentration against pressure in the flow reactor. The resulting process enables access to intercepted acylketene scaffolds using volatile amine nucleophiles and has been demonstrated on the gram scale. Thermal gravimetric analysis was used to

  报道了一种通过挤出氮气产生和使用酰基乙烯酮前体的流动化学工艺。开发合适的连续方案的关键是反应浓度与流动反应器中压力的平衡。由此产生的过程能够使用挥发性胺亲核试剂获得拦截的酰基烯酮支架，并且已经在克级上得到证明。热重分析用于指导各种酰基乙烯酮前体的反应器盘管的温度设定点。证明了两种反应性中间体（均来自氮挤压）的同时产生和反应。
• Efficient aerobic and DMSO-oxidative sulfenylation reactions catalyzed by Na2S2O3
  作者：Habiballah Shafie、Mohammad Abbasi

  DOI：10.1016/j.tet.2024.133989

  日期：2024.5

  Two efficient acid-base-free procedures are introduced for the sulfenylation of cyclic enaminone compounds under aerobic and DMSO-oxidative conditions catalyzed by NaSO. According to procedures, a mixture of an aryl thiol and a cyclic enaminone are reacting together in DMF (aerobic oxidative conditions) or DMSO in the presence of a catalytic amount of NaSO (0.1 equiv in DMSO and 0.4 equiv in DMF) to

  引入了两种有效的无酸碱程序，用于 NaSO 催化的有氧和 DMSO 氧化条件下环状烯胺酮化合物的磺酰化。根据程序，芳基硫醇和环状烯胺酮的混合物在DMF（有氧氧化条件）或DMSO中，在催化量的Na2SO4（DMSO中0.1当量，DMF中0.4当量）存在下一起反应，产生相关的高产率的α-磺酰化环状烯胺酮化合物。在没有 NaSO 的情况下，这两种反应都不能令人满意，因此 DMF（有氧条件）中的反应根本不会产生任何产物，并且 DMSO 中的转化率在 24 小时内进展不到 50%。
• de Groot,A.; Jansen,B.J.M., Recueil des Travaux Chimiques des Pays-Bas, 1979, vol. 98, p. 487 - 492
  作者：de Groot,A.、Jansen,B.J.M.

  DOI：——

  日期：——
• ARBUZOV B. A.; BELKIN YU. V.; POLEZHAEVA N. A., IZV. AN CCCP. CEP. XIM., 1979, HO 8, 1893-1895
  作者：ARBUZOV B. A.、 BELKIN YU. V.、 POLEZHAEVA N. A.

  DOI：——

  日期：——
• Electrolytic Partial Fluorination of Organic Compounds. 17. Regiospecific Anodic Fluorination of Sulfides Bearing Electron-Withdrawing Substituents at the Position .alpha. to the Sulfur Atom
  作者：Toshio Fuchigami、Moriyasu Shimojo、Akinori Konno

  DOI：10.1021/jo00116a037

  日期：1995.6

  Regiospecific monofluorination of various sulfides bearing electron-withdrawing substituents, cyano, ester, acyl, amino, and phosphonate groups,at their alpha-positions was successfully carried out by the anodic oxidation of the sulfides in Et(3)N . 3HF/MeCN using an undivided cell. Fluorine was introduced at the position alpha to the sulfur atom selectively. Fluorination of alpha-(phenylthio)-substituted cyclic carbonyl compounds was also successful. Furthermore, anodic alpha,alpha-difluorination of ethyl alpha-(phenylthio)acetate was also successfully carried out although a large amount of electricity was required.