1,5-diphenyl-1,5-bis(phenylsulfenyl)pentan-3-one | 13004-86-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1,5-diphenyl-1,5-bis(phenylsulfenyl)pentan-3-one
• 英文别名: 1,5-diphenyl-1,5-bis-phenylsulfanyl-pentan-3-one；1,5-Diphenyl-1,5-bis-phenylmercapto-pentan-3-on；1,5-Diphenyl-1,5-bis(phenylsulfanyl)pentan-3-one；1,5-diphenyl-1,5-bis(phenylsulfanyl)pentan-3-one
• CAS: 13004-86-9
• 化学式: C₂₉H₂₆OS₂
• 分子量: 454.657
• InChiKey: GUOIAKFCEQKYMW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  67.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,5-diphenyl-1,5-bis(phenylsulfenyl)pentan-3-one 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以89%的产率得到1,5-bis-benzenesulfonyl-1,5-diphenyl-pentan-3-one
  参考文献：
  名称：

  Synthesis and antibacterial and antifungal evaluation of some chalcone based sulfones and bisulfones

  摘要：

  Two series of chalcone based sulfone and bisulfone derivatives were synthesized using chalcone, thiophenol and sodium metal at room temperature, followed by oxidation of chalcone sulfides with m-CPBA at 0 degrees C in a novel method. Both sulfones and bisulfones were evaluated for their antimicrobial activities against Aspergillus niger and Candida albicans (yeast), Bacillus subtilis and Staphylococcus aureus (Gram (+) bacteria) and Pseudomonas aeruginosa and Salmonella typhimurium (Gram (-) bacteria) strains. Among them, compounds 2c, 3c, 6c, 7c, 8c and 9c have shown high antifungal activity against C albicans compare to reference drugs viz. Amphotericin-B and Nystatin. Compound 1c has shown slightly better antibacterial activity against B. subtilis and compounds 5c, 6c and 7c have shown excellent antibacterial activity against S. typhimurium in compare to reference drugs Ampicillin and Kanamycin. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.09.004
• 作为产物：
  描述：

  苯硫酚 、 二苄叉丙酮 在 sodium 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以90%的产率得到1,5-diphenyl-1,5-bis(phenylsulfenyl)pentan-3-one
  参考文献：
  名称：

  Synthesis and antibacterial and antifungal evaluation of some chalcone based sulfones and bisulfones

  摘要：

  Two series of chalcone based sulfone and bisulfone derivatives were synthesized using chalcone, thiophenol and sodium metal at room temperature, followed by oxidation of chalcone sulfides with m-CPBA at 0 degrees C in a novel method. Both sulfones and bisulfones were evaluated for their antimicrobial activities against Aspergillus niger and Candida albicans (yeast), Bacillus subtilis and Staphylococcus aureus (Gram (+) bacteria) and Pseudomonas aeruginosa and Salmonella typhimurium (Gram (-) bacteria) strains. Among them, compounds 2c, 3c, 6c, 7c, 8c and 9c have shown high antifungal activity against C albicans compare to reference drugs viz. Amphotericin-B and Nystatin. Compound 1c has shown slightly better antibacterial activity against B. subtilis and compounds 5c, 6c and 7c have shown excellent antibacterial activity against S. typhimurium in compare to reference drugs Ampicillin and Kanamycin. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.09.004

文献信息

• Conjugate addition of indoles and thiols with electron-deficient olefins catalyzed by Bi(OTf)3
  作者：M.Mujahid Alam、Ravi Varala、Srinivas R. Adapa

  DOI：10.1016/s0040-4039(03)01089-x

  日期：2003.6

  Conjugate addition of indoles and thiols with a variety of electron-deficient olefins mediated by a catalytic amount of Bi(OTf)3 at ambient temperature to afford the corresponding Michael adducts in good to excellent yields with high selectivity is reported.

  据报道，在环境温度下，吲哚和硫醇与催化量的Bi（OTf）3介导的各种电子不足的烯烃共轭加成，可以提供高产率至高产率的高选择性的相应迈克尔加合物。
• KF/Al₂O₃-Mediated Michael Addition of Thiols to Electron‐Deficient Olefins
  作者：F. Matloubi Moghaddam、G. Rezanejade Bardajee、R. Oftadeh Chadorneshine Veranlou

  DOI：10.1080/00397910500189783

  日期：2005.9.1

  Abstract Potassium fluoride supported on alumina efficiently catalyzes Michael addition of aromatic and aliphatic thiols to a variety of conjugated alkenes such as α,β‐unsaturated carbonyl compounds, carboxylic esters, amides, nitriles and chalcones. The Michael adducts are produced in good to excellent yields and relatively in short times. The catalyst can be recycled for subsequent reactions without

  摘要 氧化铝负载的氟化钾有效地催化芳香族和脂肪族硫醇与各种共轭烯烃的迈克尔加成反应，如α,β-不饱和羰基化合物、羧酸酯、酰胺、腈和查耳酮。迈克尔加合物以良好到极好的收率和相对较短的时间产生。催化剂可以循环用于后续反应，而不会显着降低效率。
• Ruhemann, Journal of the Chemical Society, 1905, vol. 87, p. 20
  作者：Ruhemann

  DOI：——

  日期：——
• Posner, Chemische Berichte, 1902, vol. 35, p. 814
  作者：Posner

  DOI：——

  日期：——
• Synthesis and antibacterial and antifungal evaluation of some chalcone based sulfones and bisulfones
  作者：Naveen Kumar Konduru、Sunita Dey、Mohammad Sajid、Mohammad Owais、Naseem Ahmed

  DOI：10.1016/j.ejmech.2012.09.004

  日期：2013.1

  Two series of chalcone based sulfone and bisulfone derivatives were synthesized using chalcone, thiophenol and sodium metal at room temperature, followed by oxidation of chalcone sulfides with m-CPBA at 0 degrees C in a novel method. Both sulfones and bisulfones were evaluated for their antimicrobial activities against Aspergillus niger and Candida albicans (yeast), Bacillus subtilis and Staphylococcus aureus (Gram (+) bacteria) and Pseudomonas aeruginosa and Salmonella typhimurium (Gram (-) bacteria) strains. Among them, compounds 2c, 3c, 6c, 7c, 8c and 9c have shown high antifungal activity against C albicans compare to reference drugs viz. Amphotericin-B and Nystatin. Compound 1c has shown slightly better antibacterial activity against B. subtilis and compounds 5c, 6c and 7c have shown excellent antibacterial activity against S. typhimurium in compare to reference drugs Ampicillin and Kanamycin. (C) 2012 Elsevier Masson SAS. All rights reserved.