1,6-diphenyl-5-(phenylsulfanyl)piperidin-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1,6-diphenyl-5-(phenylsulfanyl)piperidin-2-one
• 英文别名: (5S,6R)-1,6-diphenyl-5-phenylsulfanylpiperidin-2-one
• 化学式: C₂₃H₂₁NOS
• 分子量: 359.492
• InChiKey: AVBBTMMRNYBDIZ-JTHBVZDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  45.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,6-diphenyl-5-(phenylsulfanyl)piperidin-2-one 在 Raney nickel 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以89%的产率得到1,6-diphenylpiperidin-2-one
  参考文献：
  名称：

  Electrophilic intramolecular cyclization of functional dervatives of unsaturated compounds: VII. Synthesis of 5-arylsulfanyl-6-phenylpiperidin-2-ones in the absence of salt additives and their selective reduction and oxidation

  摘要：

  Cinnamylacetamides reacted with arylsulfenyl chlorides in chloroform in the absence of LiClO4 affording 5-(arylsulfanyl)-6-phenylpiperidin-2-ones. Their reduction with a system LiAlH4-AlCl3 resulted in 3-(tolylsulfanyl)-1,2-diphenylpiperidine, and with Raney nickel, in 1-aryl-6-phenylpiperidin-2-ones. The latter treated with LiAlH4-AlCl3 were converted into 1-aryl-2-phenyl-piperidines. The oxidation of 5-(arylsulfanyl)-6-phenylpiperidin-2-ones with hydrogen peroxide in acetone led to the formation of 5-sulfinyl-, and with oxone, to 5-sulfonyl derivatives.

  DOI：

  10.1134/s1070428015020165
• 作为产物：
  描述：

  N,5-diphenylpent-4-enamide 、 苯次磺酰氯 在 lithium perchlorate 作用下， 以 溶剂黄146 为溶剂， 反应 4.0h， 以61%的产率得到1,6-diphenyl-5-(phenylsulfanyl)piperidin-2-one
  参考文献：
  名称：

  不饱和化合物功能衍生物的分子内亲电环化：I.由肉桂基乙酰胺和芳基亚磺酰氯合成5-芳基硫烷基-6-苯基哌啶-2-酮

  摘要：

  在高氯酸锂存在下，在乙酸中与苯基（4-甲苯基）亚磺酰氯发生反应时，肉桂基乙酸的无阻N-烷基（芳基）酰胺发生选择性环化成5-芳基硫烷基-6-苯基哌啶-2-酮。在类似条件下，氮原子上带有大取代基的酰胺与芳基亚硫酰氯的反应，生成5-芳基硫烷基-6-苯基四氢吡喃-2-亚胺基高氯酸盐，通过用乙醇水溶液处理将其转化为相应的吡喃-2-酮衍生物。 。

  DOI：

  10.1134/s1070428011080057

文献信息

• Intramolecular electrophilic cyclization of functional derivatives of unsaturated Compounds: I. Synthesis of 5-arylsulfanyl-6-phenylpiperidin-2-ones from cinnamylacetamides and arylsulfenyl chlorides
  作者：A. I. Vas’kevich、N. M. Tsizorik、E. B. Rusanov、V. I. Stanitets、M. V. Vovk

  DOI：10.1134/s1070428011080057

  日期：2011.8

  nonhindered N-alkyl(aryl)amides of cinnamylacetic acid in the reaction with phenyl(4-tolyl)sulfenyl chlorides in acetic acid in the presence of lithium perchlorate undergo a selective cyclization into 5-arylsulfanyl-6-phenylpiperidin-2-ones. Under similar conditions the reaction with arylsulfenyl chlorides of amides containing bulky substituents at the nitrogen atom resulted in 5-arylsulfanyl-6-phenyl

  在高氯酸锂存在下，在乙酸中与苯基（4-甲苯基）亚磺酰氯发生反应时，肉桂基乙酸的无阻N-烷基（芳基）酰胺发生选择性环化成5-芳基硫烷基-6-苯基哌啶-2-酮。在类似条件下，氮原子上带有大取代基的酰胺与芳基亚硫酰氯的反应，生成5-芳基硫烷基-6-苯基四氢吡喃-2-亚胺基高氯酸盐，通过用乙醇水溶液处理将其转化为相应的吡喃-2-酮衍生物。 。
• Electrophilic intramolecular cyclization of functional dervatives of unsaturated compounds: VII. Synthesis of 5-arylsulfanyl-6-phenylpiperidin-2-ones in the absence of salt additives and their selective reduction and oxidation
  作者：N. M. Tsizorik、A. I. Vas’kevich、R. I. Vas’kevich、M. V. Vovk

  DOI：10.1134/s1070428015020165

  日期：2015.2

  Cinnamylacetamides reacted with arylsulfenyl chlorides in chloroform in the absence of LiClO4 affording 5-(arylsulfanyl)-6-phenylpiperidin-2-ones. Their reduction with a system LiAlH4-AlCl3 resulted in 3-(tolylsulfanyl)-1,2-diphenylpiperidine, and with Raney nickel, in 1-aryl-6-phenylpiperidin-2-ones. The latter treated with LiAlH4-AlCl3 were converted into 1-aryl-2-phenyl-piperidines. The oxidation of 5-(arylsulfanyl)-6-phenylpiperidin-2-ones with hydrogen peroxide in acetone led to the formation of 5-sulfinyl-, and with oxone, to 5-sulfonyl derivatives.