2,2-dimethylpropanoic acid 1-[bis(methylsulfanyl)methyl]-3-{(but-3-enoyl)[2-(3,4-dimethoxyphenyl)ethyl]amino}-3-oxopropyl ester | 496863-42-4

• 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: 2,2-dimethylpropanoic acid 1-[bis(methylsulfanyl)methyl]-3-{(but-3-enoyl)[2-(3,4-dimethoxyphenyl)ethyl]amino}-3-oxopropyl ester
• 英文别名: [4-[But-3-enoyl-[2-(3,4-dimethoxyphenyl)ethyl]amino]-1,1-bis(methylsulfanyl)-4-oxobutan-2-yl] 2,2-dimethylpropanoate
• CAS: 496863-42-4
• 化学式: C₂₅H₃₇NO₆S₂
• 分子量: 511.704
• InChiKey: GIKIWQQXOGZNEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  34
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  133
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,2-dimethylpropanoic acid 1-[bis(methylsulfanyl)methyl]-3-{(but-3-enoyl)[2-(3,4-dimethoxyphenyl)ethyl]amino}-3-oxopropyl ester 在 dimethyl(methylthio)sulfonium tetrafluoroborate 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以66%的产率得到N-[2-(3,4-dimethoxyphenyl)ethyl]-N-[5-(methylsulfanyl)furan-2-yl]but-3-enamide
  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 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 2,2-dimethylpropanoic acid 1-[bis(methylsulfanyl)methyl]-3-{(but-3-enoyl)[2-(3,4-dimethoxyphenyl)ethyl]amino}-3-oxopropyl ester
  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.