2-(1-Hydroxy-1-methylethyl)-4-methoxyfuro<2,3-b>chinolin | 110744-50-8

• 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: 2-(1-Hydroxy-1-methylethyl)-4-methoxyfuro<2,3-b>chinolin
• 英文别名: platydesmine；2-(1-Hydroxy-1-methylethyl)dictamnin；4-methoxy-α,α-dimethylfuro[2,3-b]quinoline-2-methanol；2-(4-Methoxyfuro[2,3-b]quinolin-2-yl)propan-2-ol
• CAS: 110744-50-8
• 化学式: C₁₅H₁₅NO₃
• 分子量: 257.289
• InChiKey: KPQVKOCVRRAGSW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  55.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(1-Hydroxy-1-methylethyl)-4-methoxyfuro<2,3-b>chinolin 在 platinum(IV) oxide 、 rhodium(III) oxide 氢气 作用下， 以 乙醇 为溶剂， 以60%的产率得到Platydesmin
  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：

  3-Iod-4-methoxy-2(1H)chinolinon 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 作用下， 以 三乙胺 为溶剂， 反应 11.0h， 生成 2-(1-Hydroxy-1-methylethyl)-4-methoxyfuro<2,3-b>chinolin
  参考文献：
  名称：

  Reisch, Johannes; Bathe, Andreas, Liebigs Annalen der Chemie, 1988, p. 69 - 74

  摘要：

  DOI：

文献信息

• Synthesis of (+)-Myrtopsine, (+)-7,8-Dimethoxymyrtopsine, and Related 2,3-Dihydro-3-hydroxy-2-(1-hydroxy-1-methylethyl)benzofuran Natural Products
  作者：Barry B. Snider、Xiaoxing Wu

  DOI：10.3987/com-06-s(w)20

  日期：——
• REISCH, JOHANNES;BATHE, ANDREAS, LIEBIGS ANN. CHEM.,(1988) N 1, 69-73
  作者：REISCH, JOHANNES、BATHE, ANDREAS

  DOI：——

  日期：——
• Reisch, Johannes; Bathe, Andreas, Liebigs Annalen der Chemie, 1988, p. 69 - 74
  作者：Reisch, Johannes、Bathe, Andreas

  DOI：——

  日期：——
• 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).