1-[(E)-3-bromoprop-2-enyl]-6-(trifluoromethyl)-3,4-dihydropyridin-2-one | 184157-43-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1-[(E)-3-bromoprop-2-enyl]-6-(trifluoromethyl)-3,4-dihydropyridin-2-one
• CAS: 184157-43-5
• 化学式: C₉H₉BrF₃NO
• 分子量: 284.076
• InChiKey: RJCFNPRBCSWJLK-GORDUTHDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-[(E)-3-bromoprop-2-enyl]-6-(trifluoromethyl)-3,4-dihydropyridin-2-one 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 5.0h， 以64%的产率得到3,7,8,8a-Tetrahydro-8a-trifluoromethyl-5(6H)-indolizinone
  参考文献：
  名称：

  Generation of 6-(Trifluoromethyl)-4,5-dihydro-2(3H)-pyridone and the Application to Synthesis of Some Fused Nitrogen Heterocycles Carrying a Trifluoromethyl Group on the Bridgehead Position via Radical Cyclization of Dihydropyridones

  摘要：

  Staudinger/aza-Wittig reaction of 6,6,6-trifluoro-5-oxohexanoyl azide with PPh(3) or PBu(3) was examined. A reactive intermediate acyl imine 1 was trapped by methanol. Without nucleophile, isomerized enamide form 3 was obtained. N-Iodobenzoylation and N-haloalkylation of 3 and following radical cyclization via the 5-exo or g-exo mode gave benzoindolizidinone, indolizidinone, and quinolizidinone derivatives 10-14, which have a trifluoromethyl group at the bridgehead position adjacent to nitrogen. Although LiAlH4 reduction of 10 and 11 gave a mixture of saturated benzoindolizidine 15 and amino alcohol 16, reduction with BH3/THF selectively gave the desired 15 and indolizidine 17 from 13.

  DOI：

  10.1021/jo961030g
• 作为产物：
  描述：

  6,6,6-Trifluoro-5-oxohexanoyl chloride 在 1,1,1-三甲基-N-(三苯基正膦亚基)硅烷胺 、 sodium hydride 、 sodium iodide 作用下， 以 四氢呋喃 、 paraffin 为溶剂， 反应 73.0h， 生成 1-[(E)-3-bromoprop-2-enyl]-6-(trifluoromethyl)-3,4-dihydropyridin-2-one
  参考文献：
  名称：

  Generation of 6-(Trifluoromethyl)-4,5-dihydro-2(3H)-pyridone and the Application to Synthesis of Some Fused Nitrogen Heterocycles Carrying a Trifluoromethyl Group on the Bridgehead Position via Radical Cyclization of Dihydropyridones

  摘要：

  Staudinger/aza-Wittig reaction of 6,6,6-trifluoro-5-oxohexanoyl azide with PPh(3) or PBu(3) was examined. A reactive intermediate acyl imine 1 was trapped by methanol. Without nucleophile, isomerized enamide form 3 was obtained. N-Iodobenzoylation and N-haloalkylation of 3 and following radical cyclization via the 5-exo or g-exo mode gave benzoindolizidinone, indolizidinone, and quinolizidinone derivatives 10-14, which have a trifluoromethyl group at the bridgehead position adjacent to nitrogen. Although LiAlH4 reduction of 10 and 11 gave a mixture of saturated benzoindolizidine 15 and amino alcohol 16, reduction with BH3/THF selectively gave the desired 15 and indolizidine 17 from 13.

  DOI：

  10.1021/jo961030g

文献信息

• Generation of 6-(Trifluoromethyl)-4,5-dihydro-2(3<i>H</i>)-pyridone and the Application to Synthesis of Some Fused Nitrogen Heterocycles Carrying a Trifluoromethyl Group on the Bridgehead Position via Radical Cyclization of Dihydropyridones
  作者：Takashi Okano、Tsutomu Sakaida、Shoji Eguchi

  DOI：10.1021/jo961030g

  日期：1996.1.1

  Staudinger/aza-Wittig reaction of 6,6,6-trifluoro-5-oxohexanoyl azide with PPh(3) or PBu(3) was examined. A reactive intermediate acyl imine 1 was trapped by methanol. Without nucleophile, isomerized enamide form 3 was obtained. N-Iodobenzoylation and N-haloalkylation of 3 and following radical cyclization via the 5-exo or g-exo mode gave benzoindolizidinone, indolizidinone, and quinolizidinone derivatives 10-14, which have a trifluoromethyl group at the bridgehead position adjacent to nitrogen. Although LiAlH4 reduction of 10 and 11 gave a mixture of saturated benzoindolizidine 15 and amino alcohol 16, reduction with BH3/THF selectively gave the desired 15 and indolizidine 17 from 13.