methyl N-benzyloxycarbonyl 6-[difluoro(2-naphthyl)methyl]-4-(hydroxymethyl)-1,4-dihydropyridin-3-carboxylate | 1235994-58-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl N-benzyloxycarbonyl 6-[difluoro(2-naphthyl)methyl]-4-(hydroxymethyl)-1,4-dihydropyridin-3-carboxylate
• 英文别名: 1-O-benzyl 3-O-methyl (4S)-6-[difluoro(naphthalen-2-yl)methyl]-4-(hydroxymethyl)-4H-pyridine-1,3-dicarboxylate
• CAS: 1235994-58-7
• 化学式: C₂₇H₂₃F₂NO₅
• 分子量: 479.48
• InChiKey: AAUNBWPRSDHKBA-OAQYLSRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  在 sodium tetrahydroborate 作用下， 以 水 、 乙腈 为溶剂， 生成 methyl N-benzyloxycarbonyl 6-[difluoro(2-naphthyl)methyl]-4-(hydroxymethyl)-1,4-dihydropyridin-3-carboxylate 、 methyl N-benzyloxycarbonyl 6-[difluoro(2-naphthyl)methyl]-4-(hydroxymethyl)-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