N-(p-Toluenesulfonyl)-3-methyl-5,6-dihydro-2(1H)-pyridinone | 130291-45-1

• 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: N-(p-Toluenesulfonyl)-3-methyl-5,6-dihydro-2(1H)-pyridinone
• 英文别名: 3-methyl-1-(toluene-4-sulfonyl)-5,6-dihydro-1H-pyridin-2-one；3-methyl-1-(4-methylphenyl)sulfonyl-5,6-dihydropyridin-2(1H)-one；5-Methyl-1-(4-methylphenyl)sulfonyl-2,3-dihydropyridin-6-one
• CAS: 130291-45-1
• 化学式: C₁₃H₁₅NO₃S
• 分子量: 265.333
• InChiKey: USOZMFYPMQKIDR-UHFFFAOYSA-N

物化性质

• 沸点：
  406.1±48.0 °C(Predicted)
• 密度：
  1.270±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  62.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(p-Toluenesulfonyl)-3-methyl-5,6-dihydro-2(1H)-pyridinone 、 反-1-甲氧基-3-(三甲基硅氧基)-1,3-丁二烯 生成 (4aR,8aS)-8a-methyl-2-(4-methylphenyl)sulfonyl-3,4,4a,5-tetrahydroisoquinoline-1,6-dione
  参考文献：
  名称：

  TORISAWA, YASUHIRO;NAKAGAWA, MASAKO;ARAI, HITOE;LAI, ZIPING;HINO, TOHRU;N+, TETRAHEDRON LETT., 31,(1990) N2, C. 3195-3198

  摘要：

  DOI：
• 作为产物：
  描述：

  1-(toluene-4-sulfonyl)piperidin-2-one 在 双(三甲基硅烷基)氨基钾 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 2.75h， 生成 N-(p-Toluenesulfonyl)-3-methyl-5,6-dihydro-2(1H)-pyridinone
  参考文献：
  名称：

  Diels-Alder reactions of dihydropyridinones: synthetic entry to the manzamine A tricyclic core

  摘要：

  For the construction of the tricyclic core of manzamine A (1), the Diels-Alder reactions of some dihydropyridinones were surveyed. The N-protecting group of the dihydropyridinone played an important role in achieving a successful Diels-Alder reaction. In view of its electron-withdrawing character as well as its thermal stability, the p-toluenesulfonyl protecting group was found to be best in our synthesis. An effective method for the preparation of 3-alkyldihydropyridinones via the Michael addition to dehydroalanine derivatives has also been devised. By the utilization of a high-pressure Diels-Alder reaction of the N-tosyl-3-alkyldihydropyridinone (17) with the Danishefsky diene, a facile construction of the central pyrroloisoquinoline skeleton (21) was successfully achieved.

  DOI：

  10.1021/jo00047a031

文献信息

• Morita−Baylis−Hillman Reaction of Lactams and Lactones with Alkyl Halides and Epoxides Catalyzed by Hydroxysulfides
  作者：Irene Suarez del Villar、Ana Gradillas、Gema Domínguez、Javier Pérez-Castells

  DOI：10.1021/ol100788g

  日期：2010.5.21

  A new Morita−Baylis−Hillman reaction methodology in which alkyl halides and epoxides act as electrophiles in their reaction with lactones and lactams is shown. Catalysis is efficiently performed by hydroxy sulfides under basic conditions. The procedure works efficiently with many alkyl halides but fails with aldehydes with which a conventional acid-catalyzed procedure is used.

  显示了一种新的Morita-Baylis-Hillman反应方法，其中烷基卤化物和环氧化物在与内酯和内酰胺的反应中充当亲电子试剂。在碱性条件下，通过羟基硫化物可有效地进行催化。该方法对于许多烷基卤有效地起作用，但是对于醛而言则无效，而醛则与常规的酸催化方法一起使用。
• Synthetic studies on manzamine a II; a novel diels-alder approach to the pyrrolo[2,3-j]isoquinoline skeleton
  作者：Yasuhiro Torisawa、Masako Nakagawa、Hitoe Arai、Ziping Lai、Tohru Hino、Tadashi Nakata、Takeshi Oishi

  DOI：10.1016/s0040-4039(00)94730-0

  日期：1990.1

  An expeditious preparation of the central pyrroloisoquinoline skeleton of manzamine A (I) was achieved via the high-pressure Diels-Alder reaction of 3-alkyl-5,6-dihydro-2-pyridinone (10) with Danishefsky diene followed by deprotection and spontaneous pyrrolidine ring clousure.

  通过3-烷基-5,6-二氢-2-吡啶酮（1 0）与Danishefsky二烯的高压Diels-Alder反应，然后进行脱保护和保护，可以快速制备曼扎明A（I）的中心吡咯并异喹啉骨架。自发性吡咯烷环闭合。
• Ru-Catalyzed Cyclocarbonylation of α- and β-Allenic Sulfonamides:  Synthesis of γ- and δ-Unsaturated Lactams
  作者：Suk-Ku Kang、Kwang-Jin Kim、Chan-Mo Yu、Jeong-Wook Hwang、Young-Kyu Do

  DOI：10.1021/ol016281c

  日期：2001.9.1

  [GRAPHICS]The Ru-catalyzed cyclocarbonylation of alpha- or beta -allenic sulfonamides in the presence of Ru-3(CO)(12) (1 mol %) and Et3N (1.5 equiv) under CO atmosphere (20 atm) in dioxane at 100 degreesC for 9 h gave heterocyclic gamma- and delta -unsaturated lactams in good yields.