6,6,6-Trifluoro-5-oxohexanoyl chloride | 1027194-65-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6,6,6-Trifluoro-5-oxohexanoyl chloride
• CAS: 1027194-65-5
• 化学式: C₆H₆ClF₃O₂
• 分子量: 202.561
• InChiKey: IPACOVZMTZFFLC-UHFFFAOYSA-N

物化性质

• 沸点：
  195.4±40.0 °C(Predicted)
• 密度：
  1.354±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6,6,6-Trifluoro-5-oxohexanoyl chloride 在 lithium aluminium tetrahydride 、 偶氮二异丁腈 、 1,1,1-三甲基-N-(三苯基正膦亚基)硅烷胺 、 三正丁基氢锡 、 sodium hydride 作用下， 以 四氢呋喃 、 paraffin 、 苯 为溶剂， 反应 13.0h， 生成 4-[1-(Trifluoromethyl)-2,3-dihydroisoindol-1-yl]butan-1-ol
  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：

  6,6,6-三氟-5-氧代己酸 在 氯化亚砜 作用下， 反应 2.5h， 生成 6,6,6-Trifluoro-5-oxohexanoyl chloride
  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.