(+)-methyl 6-[difluoro(2-naphthyl)methyl]-4-[(R)-p-tolylsulfinylmethyl]-1,4-dihydropyridin-3-carboxylate | 1235994-46-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (+)-methyl 6-[difluoro(2-naphthyl)methyl]-4-[(R)-p-tolylsulfinylmethyl]-1,4-dihydropyridin-3-carboxylate
• CAS: 1235994-46-3
• 化学式: C₂₆H₂₃F₂NO₃S
• 分子量: 467.536
• InChiKey: LRONPEIINVMRMC-OGPYBGEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.21
• 重原子数：
  33.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  55.4
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (+)-methyl 6-[difluoro(2-naphthyl)methyl]-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63%的产率得到(+)-methyl N-benzyloxycarbonyl 6-[difluoro(2-naphthyl)methyl]-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：

  (+)-(2Z,4E)-1,1-difluoro-1-(2-naphthyl)-5-[(R)-p-tolylsulfinyl]penta-2,4-dien-2-amine 、 丙炔酸甲酯 以 四氢呋喃 、 甲苯 为溶剂， 以79 mg的产率得到(+)-methyl 6-[difluoro(2-naphthyl)methyl]-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