2-(4-chloro-phenylsulfanyl)-cyclohexanone | 5409-84-7

• 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-(4-chloro-phenylsulfanyl)-cyclohexanone
• 英文别名: 2-(4-Chlor-phenylmercapto)-cyclohexanon；2-(4-Chlorphenylthio)-cyclohexanon；2-(p-Chlorphenylthio)-cyclohexanon；2-p-Chlorphenylthio-cyclohexanon；2-[(4-Chlorophenyl)sulfanyl]cyclohexan-1-one；2-(4-chlorophenyl)sulfanylcyclohexan-1-one
• CAS: 5409-84-7
• 化学式: C₁₂H₁₃ClOS
• mdl: MFCD04274938
• 分子量: 240.754
• InChiKey: AJLLFHAFVYCXJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.416
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(4-chloro-phenylsulfanyl)-cyclohexanone 在 iodine pentafluoride-pyridine-hydrogen fluoride 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以76%的产率得到2-[(4-chlorophenyl)thio]-2-fluorocyclohexanone
  参考文献：
  名称：

  IF5–pyridine–HF: air- and moisture-stable fluorination reagent

  摘要：

  IF5-pyridine-HF, an air- and moisture-stable solid, can be used as a fluorination reagent for the introduction of fluorine atoms to the alpha-position of the sulfur atom in sulfides. The desulfurizing-fluorination reactions of benzylic sulfides, thioacetals, and 2-(methylthio)-1,3-dithiane derivatives were also performed using this reagent. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.09.104
• 作为产物：
  描述：

  4,4'-二氯二苯二硫醚 、 环己酮 在 potassium phosphate 作用下， 以 二甲基亚砜 为溶剂， 反应 18.0h， 以63%的产率得到2-(4-chloro-phenylsulfanyl)-cyclohexanone
  参考文献：
  名称：

  α-Organylchalcogenation of aldehydes and ketones with diorganyl dichalcogenides promoted by K3PO4

  摘要：

  A new catalytic method for direct alpha-organylchalcogenation of aldehydes and ketones has been developed. When various aldehydes and ketones were allowed to react with diorganyl dichalcogenides in the presence of K3PO4, under mild reaction conditions, the corresponding alpha-organylseleno and alpha-arylthio aldehydes and ketones were obtained in good to high yields.

  DOI：

  10.1007/s00706-014-1188-7

文献信息

• Rhodium-Catalyzed Organothio Exchange Reaction of .ALPHA.-Organothioketones with Disulfides
  作者：Mieko Arisawa、Fumihiko Toriyama、Masahiko Yamaguchi

  DOI：10.1248/cpb.58.1349

  日期：——

  RhH(PPh3)4 and 1,2-bis(diphenylphosphino)ethane (dppe) catalyzed the organothio exchange reaction of α-organothioketones and organic disulfides. The reaction was affected by the structure of the substrate: α-phenylthio and α-alkylthio aryl ketones reacted effectively with diaryl and dialkyl disulfides; α-phenylthio dialkyl ketones reacted with diaryl disulfides but not with dialkyl disulfides; diaryl disulfides with electron-donating p-substituents were more reactive than those with electron-withdrawing p-substituents.

  RhH(PPh3)4和1,2-双(二苯基膦)乙烷（dppe）催化α-有机硫酮与有机二硫化物的有机硫交换反应。反应受底物结构影响：α-苯硫基和α-烷硫基芳基酮能有效与二芳基和二烷基二硫化物反应；α-苯硫基二烷基酮与二芳基二硫化物反应，但不与二烷基二硫化物反应；带有供电子基团的对位取代的二芳基二硫化物比带有吸电子基团的对位取代的二芳基二硫化物更具反应性。
• N-Chlorosuccinimide as a versatile reagent for the sulfenylation of ketones: a facile synthesis of α-ketothioethers
  作者：J.S. Yadav、B.V. Subba Reddy、Ruchi Jain、Gakul Baishya

  DOI：10.1016/j.tetlet.2008.02.136

  日期：2008.4

  The sulfenylation of ketones having alpha-hydrogens has been achieved using N-chlorosuccinimide (NCS) under mild reaction conditions to produce alpha-ketothioethers in excellent yields with high selectivity. The use of NCS makes this method quite simple, convenient and practical. (C) 2008 Published by Elsevier Ltd.
• Jilek,J.O. et al., Collection of Czechoslovak Chemical Communications, 1971, vol. 36, p. 2824 - 2830
  作者：Jilek,J.O. et al.

  DOI：——

  日期：——
• α-Organylchalcogenation of aldehydes and ketones with diorganyl dichalcogenides promoted by K3PO4
  作者：Barahman Movassagh、Ali Yousefi

  DOI：10.1007/s00706-014-1188-7

  日期：2014.7

  A new catalytic method for direct alpha-organylchalcogenation of aldehydes and ketones has been developed. When various aldehydes and ketones were allowed to react with diorganyl dichalcogenides in the presence of K3PO4, under mild reaction conditions, the corresponding alpha-organylseleno and alpha-arylthio aldehydes and ketones were obtained in good to high yields.
• IF5–pyridine–HF: air- and moisture-stable fluorination reagent
  作者：Shoji Hara、Miki Monoi、Ryosuke Umemura、Chiaki Fuse

  DOI：10.1016/j.tet.2012.09.104

  日期：2012.12

  IF5-pyridine-HF, an air- and moisture-stable solid, can be used as a fluorination reagent for the introduction of fluorine atoms to the alpha-position of the sulfur atom in sulfides. The desulfurizing-fluorination reactions of benzylic sulfides, thioacetals, and 2-(methylthio)-1,3-dithiane derivatives were also performed using this reagent. (C) 2012 Elsevier Ltd. All rights reserved.