1-[2-(3,4-dimethoxyphenyl)ethyl]-6-(methylsulfanyl)-2,3,3a,4,5,6-hexahydro-1H-indole-2,5-dione | 496863-44-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-[2-(3,4-dimethoxyphenyl)ethyl]-6-(methylsulfanyl)-2,3,3a,4,5,6-hexahydro-1H-indole-2,5-dione
• 英文别名: 1-[2-(3,4-Dimethoxyphenyl)ethyl]-6-methylsulfanyl-3,3a,4,6-tetrahydroindole-2,5-dione
• CAS: 496863-44-6
• 化学式: C₁₉H₂₃NO₄S
• 分子量: 361.462
• InChiKey: DODIXQBKYHTGFJ-UHFFFAOYSA-N

物化性质

• 沸点：
  591.2±50.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  81.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-[2-(3,4-dimethoxyphenyl)ethyl]-6-(methylsulfanyl)-2,3,3a,4,5,6-hexahydro-1H-indole-2,5-dione 在 dimethyl(methylthio)sulfonium tetrafluoroborate 作用下， 以 乙腈 为溶剂， 反应 0.17h， 以74%的产率得到1-[2-(3,4-dimethoxyphenyl)ethyl]-5-hydroxy-2,3-dihydroindol-2-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：

  N-(3,4-二甲氧基苯乙基)乙酰胺 在 正丁基锂 、 molecular sieve 、 dimethyl(methylthio)sulfonium tetrafluoroborate 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 8.5h， 生成 1-[2-(3,4-dimethoxyphenyl)ethyl]-6-(methylsulfanyl)-2,3,3a,4,5,6-hexahydro-1H-indole-2,5-dione
  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.