(S)-7,8-Dimethoxy-3,10-dimethyl-3,4-dihydro-2H-benzo[b][1,6]naphthyridin-1-one | 453556-54-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (S)-7,8-Dimethoxy-3,10-dimethyl-3,4-dihydro-2H-benzo[b][1,6]naphthyridin-1-one
• CAS: 453556-54-2
• 化学式: C₁₆H₁₈N₂O₃
• 分子量: 286.331
• InChiKey: RIXIXBDBHFBWFL-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.23
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  60.45
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (S)-7,8-Dimethoxy-3,10-dimethyl-3,4-dihydro-2H-benzo[b][1,6]naphthyridin-1-one 在 氢氧化钾 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Influence of the C(4)C(3)CO dihedral angle of chiral NADH mimics on the stereoselectivity of reductions

  摘要：

  Herein we report the stereoselective synthesis of new chiral NADH mimics 2 and 13 of the benzo [b]-1,6-naphthryridine series. The synthesis of 2 and 13 relies upon a Friedlander-type condensation between the amino imine 3 and the piperidine-2,4-dione 4 bearing a stereogenic center at C(6). The resulting NADH models were involved in the reduction of methyl benzoylformate. A comparison of their performance with that of previously reported NADH mimics such as model 1, throws now light on the role played by the C(4) C(3)-C-O dihedral angle (alpha) on the stereoselectively of the hydride transfer. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00101-5
• 作为产物：
  描述：

  methyl (3S)-3-[N-(p-methoxybenzyl)-N-((ethoxycarbonyl)acetyl)amino]butyrate 在 ammonium cerium(IV) nitrate 、 硫酸 、 sodium methylate 作用下， 以 四氢呋喃 、 水 、 溶剂黄146 、 乙腈 为溶剂， 反应 10.0h， 生成 (S)-7,8-Dimethoxy-3,10-dimethyl-3,4-dihydro-2H-benzo[b][1,6]naphthyridin-1-one
  参考文献：
  名称：

  Influence of the C(4)C(3)CO dihedral angle of chiral NADH mimics on the stereoselectivity of reductions

  摘要：

  Herein we report the stereoselective synthesis of new chiral NADH mimics 2 and 13 of the benzo [b]-1,6-naphthryridine series. The synthesis of 2 and 13 relies upon a Friedlander-type condensation between the amino imine 3 and the piperidine-2,4-dione 4 bearing a stereogenic center at C(6). The resulting NADH models were involved in the reduction of methyl benzoylformate. A comparison of their performance with that of previously reported NADH mimics such as model 1, throws now light on the role played by the C(4) C(3)-C-O dihedral angle (alpha) on the stereoselectively of the hydride transfer. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00101-5