3-Iod-4,6,8-trimethoxy-chinolin-2(1H)-on | 156863-08-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 3-Iod-4,6,8-trimethoxy-chinolin-2(1H)-on
• 英文别名: 3-iodo-4,6,8-trimethoxy-2(1H)-quinolinone；3-iodo-4,6,8-trimethoxy-1H-quinolin-2-one
• CAS: 156863-08-0
• 化学式: C₁₂H₁₂INO₄
• 分子量: 361.136
• InChiKey: UKDGERRQHAZMGQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-Iod-4,6,8-trimethoxy-chinolin-2(1H)-on 在 platinum(IV) oxide 、 rhodium(III) oxide bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 氢气 、 三乙胺 作用下， 以 乙醇 为溶剂， 25.0 ℃ 、1000.0 kPa 条件下， 反应 12.0h， 生成 2,3,-dihydro-2-(1-hydroxyisopropyl)-4,6,8-trimethoxyfuro<2,3-b>quinoline
  参考文献：
  名称：

  Acetylenchemie, 33. Mitt.: Synthese von 2-substituierten Dihydrofuro[2,3-b]chinolinen

  摘要：

  The reaction of 3-iodo-4-methoxy-2(1H)-quinolinone (1) and 3-iodo-4,6,8-trimethoxy-2(1H)-quinolinone (2) with 2-methyl-3-butyn-2-ol under modified Heck-conditions gave the 2-substituted derivatives 2-(1-hydroxy-1-methylethyl)4-methoxyfuro[2,3-b]-quinoline (3) and 2-(1-hydroxy-1-methylethyl-4,6,8-trimethoxyfuro[2,3-b]-quinoline (4). By a subsequent hydrogenation-reaction with a homogeneous catalyst (PtO2/Rh2O3), the furoquinoline-derivatives yielded the dihytrofuro[2,3-b]quinolines, identified as 2-(1-hydroxy-1-methylethyl-4-methoxy-2,3-dihydrofuro[2,3-b]quinoline (5) (racemic platydesmine) and 2-(1-hydroxy-1-methylethyl)-4,6,8-trimethoxy-2,3-dihydrofuro[2,3-b]quinoline (6) (racemic precursor of O4-methylptelefolonium salt).

  DOI：

  10.1007/bf00818167
• 作为产物：
  描述：

  重氮甲烷 、 4-Hydroxy-3-iod-6,8-dimethoxy-chinolin-2(1H)-on 以 乙醚 、 乙醇 为溶剂， 反应 6.0h， 以40%的产率得到3-Iod-4,6,8-trimethoxy-chinolin-2(1H)-on
  参考文献：
  名称：

  Acetylenchemie, 33. Mitt.: Synthese von 2-substituierten Dihydrofuro[2,3-b]chinolinen

  摘要：

  The reaction of 3-iodo-4-methoxy-2(1H)-quinolinone (1) and 3-iodo-4,6,8-trimethoxy-2(1H)-quinolinone (2) with 2-methyl-3-butyn-2-ol under modified Heck-conditions gave the 2-substituted derivatives 2-(1-hydroxy-1-methylethyl)4-methoxyfuro[2,3-b]-quinoline (3) and 2-(1-hydroxy-1-methylethyl-4,6,8-trimethoxyfuro[2,3-b]-quinoline (4). By a subsequent hydrogenation-reaction with a homogeneous catalyst (PtO2/Rh2O3), the furoquinoline-derivatives yielded the dihytrofuro[2,3-b]quinolines, identified as 2-(1-hydroxy-1-methylethyl-4-methoxy-2,3-dihydrofuro[2,3-b]quinoline (5) (racemic platydesmine) and 2-(1-hydroxy-1-methylethyl)-4,6,8-trimethoxy-2,3-dihydrofuro[2,3-b]quinoline (6) (racemic precursor of O4-methylptelefolonium salt).

  DOI：

  10.1007/bf00818167

文献信息

• Acetylenchemie, 33. Mitt.: Synthese von 2-substituierten Dihydrofuro[2,3-b]chinolinen
  作者：J. Reisch、P. Nordhaus

  DOI：10.1007/bf00818167

  日期：1994.2

  The reaction of 3-iodo-4-methoxy-2(1H)-quinolinone (1) and 3-iodo-4,6,8-trimethoxy-2(1H)-quinolinone (2) with 2-methyl-3-butyn-2-ol under modified Heck-conditions gave the 2-substituted derivatives 2-(1-hydroxy-1-methylethyl)4-methoxyfuro[2,3-b]-quinoline (3) and 2-(1-hydroxy-1-methylethyl-4,6,8-trimethoxyfuro[2,3-b]-quinoline (4). By a subsequent hydrogenation-reaction with a homogeneous catalyst (PtO2/Rh2O3), the furoquinoline-derivatives yielded the dihytrofuro[2,3-b]quinolines, identified as 2-(1-hydroxy-1-methylethyl-4-methoxy-2,3-dihydrofuro[2,3-b]quinoline (5) (racemic platydesmine) and 2-(1-hydroxy-1-methylethyl)-4,6,8-trimethoxy-2,3-dihydrofuro[2,3-b]quinoline (6) (racemic precursor of O4-methylptelefolonium salt).