1-(2-methoxy-4,5,6,7-tetrahydrofuro[2,3-b]pyridin-7-yl)pent-4-en-1-one | 496863-40-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2-methoxy-4,5,6,7-tetrahydrofuro[2,3-b]pyridin-7-yl)pent-4-en-1-one
• 英文别名: 1-(2-methoxy-5,6-dihydro-4H-furo[2,3-b]pyridin-7-yl)pent-4-en-1-one
• CAS: 496863-40-2
• 化学式: C₁₃H₁₇NO₃
• 分子量: 235.283
• InChiKey: XHHXAYPBTPAVKD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  42.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-methoxy-4,5,6,7-tetrahydrofuro[2,3-b]pyridin-7-yl)pent-4-en-1-one 以 甲苯 为溶剂， 反应 12.0h， 以30%的产率得到9-hydroxy-1,2,6,7-tetrahydro-3H,5H-pyrido[3,2,1-ij]quinolin-3-one
  参考文献：
  名称：

  A New Construct of the cis-3a-Aryloctahydroindole Skeleton via the [4+2] Cycloaddition of Furanyl Carbamates

  摘要：

  2-methylthio-5-amidofurans containing tethered unsaturation were prepared via the reaction of dimethyl(methylthio)sulfonium tetrafluoroborate (DMTSF) with beta-alkoxy-gamma-dithiane amides. Thermolysis of these furans resulted in an intramolecular Diels-Alder reaction (IMDAF). The resulting oxa-bridged cycloadducts underwent a subsequent rearrangement to form bicyclic lactams. Model studies were directed toward mesembrine as well as the core skeleton of the 3,4-benzoerythrinane skeleton. Using this cascade sequence, a formal synthesis of the alkaloid erysotrine was accomplished.

  DOI：

  10.3987/com-02-s(m)12
• 作为产物：
  描述：

  4-戊烯酰氯 在 molecular sieve 、 dimethyl(methylthio)sulfonium tetrafluoroborate 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 1.0h， 生成 1-(2-methoxy-4,5,6,7-tetrahydrofuro[2,3-b]pyridin-7-yl)pent-4-en-1-one
  参考文献：
  名称：

  A New Construct of the cis-3a-Aryloctahydroindole Skeleton via the [4+2] Cycloaddition of Furanyl Carbamates

  摘要：

  2-methylthio-5-amidofurans containing tethered unsaturation were prepared via the reaction of dimethyl(methylthio)sulfonium tetrafluoroborate (DMTSF) with beta-alkoxy-gamma-dithiane amides. Thermolysis of these furans resulted in an intramolecular Diels-Alder reaction (IMDAF). The resulting oxa-bridged cycloadducts underwent a subsequent rearrangement to form bicyclic lactams. Model studies were directed toward mesembrine as well as the core skeleton of the 3,4-benzoerythrinane skeleton. Using this cascade sequence, a formal synthesis of the alkaloid erysotrine was accomplished.

  DOI：

  10.3987/com-02-s(m)12

文献信息

• A New Construct of the cis-3a-Aryloctahydroindole Skeleton via the [4+2] Cycloaddition of Furanyl Carbamates
  作者：Albert Padwa、Cheryl K. Eidell、Stephen M. Lynch

  DOI：10.3987/com-02-s(m)12

  日期：——

  2-methylthio-5-amidofurans containing tethered unsaturation were prepared via the reaction of dimethyl(methylthio)sulfonium tetrafluoroborate (DMTSF) with beta-alkoxy-gamma-dithiane amides. Thermolysis of these furans resulted in an intramolecular Diels-Alder reaction (IMDAF). The resulting oxa-bridged cycloadducts underwent a subsequent rearrangement to form bicyclic lactams. Model studies were directed toward mesembrine as well as the core skeleton of the 3,4-benzoerythrinane skeleton. Using this cascade sequence, a formal synthesis of the alkaloid erysotrine was accomplished.