1-(3-chloropropyl)-4-methyl-5-(toluene-4-sulfonyl)-3,4-dihydropyridin-2-one | 445306-22-9

• 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: 1-(3-chloropropyl)-4-methyl-5-(toluene-4-sulfonyl)-3,4-dihydropyridin-2-one
• 英文别名: 1-(3-Chloropropyl)-4-methyl-5-(4-methylphenyl)sulfonyl-3,4-dihydropyridin-2-one
• CAS: 445306-22-9
• 化学式: C₁₆H₂₀ClNO₃S
• 分子量: 341.859
• InChiKey: HPBLXWYGTOVDSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 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：

  1-(3-chloropropyl)-4-methyl-5-(toluene-4-sulfonyl)-3,4-dihydropyridin-2-one 在 偶氮二异丁腈 、 三正丁基氢锡 、 sodium iodide 作用下， 以 丙酮 、 苯 为溶剂， 反应 9.0h， 生成 (7S*,8R*,8aS*)-7-methyl-8-(toluene-4-sulfonyl)hexahydro-6H-indolizin-5-one
  参考文献：
  名称：

  Regioselective Reduction of 3-Sulfonyl Glutarimides to 3,4-Dihydro-5-sulfonylpyridin-2-ones. Formal Synthesis of the Indolizidine 8a-epi-Dendroprimine

  摘要：

  Sodium borohydride regioselectively reduced various 3-sulfonyl glutarimides 1 to hydroxy piperidones 2, which were further dehydrated to 3,4-dihydro-5-sulfonylpyridin-2-ones 3 in the presence of boron trifluoride. Formal synthesis of 8a-epi-dendroprimine (4) possessing an indolizidine ring system has been accomplished via intramolecular radical cyclization of cyclic vinyl sulfone 5.

  DOI：

  10.1021/jo025539p
• 作为产物：
  描述：

  N-benzyl-2-p-toluenesulfonylacetamide 在 sodium tetrahydroborate 、 三氯化铝 、 三氟化硼乙醚 、 sodium hydride 、 magnesium sulfate 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 丙酮 、 苯 为溶剂， 反应 32.5h， 生成 1-(3-chloropropyl)-4-methyl-5-(toluene-4-sulfonyl)-3,4-dihydropyridin-2-one
  参考文献：
  名称：

  Regioselective Reduction of 3-Sulfonyl Glutarimides to 3,4-Dihydro-5-sulfonylpyridin-2-ones. Formal Synthesis of the Indolizidine 8a-epi-Dendroprimine

  摘要：

  Sodium borohydride regioselectively reduced various 3-sulfonyl glutarimides 1 to hydroxy piperidones 2, which were further dehydrated to 3,4-dihydro-5-sulfonylpyridin-2-ones 3 in the presence of boron trifluoride. Formal synthesis of 8a-epi-dendroprimine (4) possessing an indolizidine ring system has been accomplished via intramolecular radical cyclization of cyclic vinyl sulfone 5.

  DOI：

  10.1021/jo025539p

文献信息

• Regioselective Reduction of 3-Sulfonyl Glutarimides to 3,4-Dihydro-5-sulfonylpyridin-2-ones. Formal Synthesis of the Indolizidine 8a-<i>e</i><i>pi</i>-Dendroprimine
  作者：Ru-Ting Hsu、Li-Ming Cheng、Nein-Chen Chang、Huo-Mu Tai

  DOI：10.1021/jo025539p

  日期：2002.7.1

  Sodium borohydride regioselectively reduced various 3-sulfonyl glutarimides 1 to hydroxy piperidones 2, which were further dehydrated to 3,4-dihydro-5-sulfonylpyridin-2-ones 3 in the presence of boron trifluoride. Formal synthesis of 8a-epi-dendroprimine (4) possessing an indolizidine ring system has been accomplished via intramolecular radical cyclization of cyclic vinyl sulfone 5.