(+)-ethyl 6-(1,1-difluorobut-3-enyl)-4-[(R)-p-tolylsulfinylmethyl]-1,4-dihydropyridin-3-carboxylate | 1235994-45-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (+)-ethyl 6-(1,1-difluorobut-3-enyl)-4-[(R)-p-tolylsulfinylmethyl]-1,4-dihydropyridin-3-carboxylate
• 英文别名: ethyl (4S)-6-(1,1-difluorobut-3-enyl)-4-[[(R)-(4-methylphenyl)sulfinyl]methyl]-1,4-dihydropyridine-3-carboxylate
• CAS: 1235994-45-2
• 化学式: C₂₀H₂₃F₂NO₃S
• 分子量: 395.47
• InChiKey: AVLHSCZPMHMHKI-YVORESIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  74.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (+)-ethyl 6-(1,1-difluorobut-3-enyl)-4-[(R)-p-tolylsulfinylmethyl]-1,4-dihydropyridin-3-carboxylate 、 氯甲酸苄酯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 以73%的产率得到(+)-ethyl N-benzyloxycarbonyl-6-(1,1-difluorobut-3-enyl)-4-[(R)-p-tolylsulfinylmethyl]-1,4-dihydropyridin-3-carboxylate
  参考文献：
  名称：

  Tandem Asymmetric Michael Reaction−Intramolecular Michael Addition. An Easy Entry to Chiral Fluorinated 1,4-Dihydropyridines

  摘要：

  A novel one-pot tandem asymmetric Hantzsch-type process has been employed to generate fluorinated 1,4-dihydropyridines (1,4-DHPs) as single diastereoisomers. It involves the condensation of (R)-(+)-allyl p-tolyl sulfoxide, fluorinated nitriles, and alkyl propiolates, giving access to a new family of enantiomerically pure fluorine-containing 1,4-DHPs.

  DOI：

  10.1021/ol101318t
• 作为产物：
  描述：

  (+)-(1E,3Z)-5,5-difluoro-1-[(R)-p-tolylsulfinyl]octa-1,3,7-trien-4-amine 、 丙炔酸乙酯 以 四氢呋喃 、 甲苯 为溶剂， 以63 mg的产率得到(+)-ethyl 6-(1,1-difluorobut-3-enyl)-4-[(R)-p-tolylsulfinylmethyl]-1,4-dihydropyridin-3-carboxylate
  参考文献：
  名称：

  Tandem Asymmetric Michael Reaction−Intramolecular Michael Addition. An Easy Entry to Chiral Fluorinated 1,4-Dihydropyridines

  摘要：

  A novel one-pot tandem asymmetric Hantzsch-type process has been employed to generate fluorinated 1,4-dihydropyridines (1,4-DHPs) as single diastereoisomers. It involves the condensation of (R)-(+)-allyl p-tolyl sulfoxide, fluorinated nitriles, and alkyl propiolates, giving access to a new family of enantiomerically pure fluorine-containing 1,4-DHPs.

  DOI：

  10.1021/ol101318t