ethyl 2-[((3aR,5R,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethylperhydrofuro[2,3-d][1,3]dioxol-6-yloxy)methyl]-6-chloro-4-phenyl-3-quinolinecarboxylate | 1203506-55-1

• 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: ethyl 2-[((3aR,5R,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethylperhydrofuro[2,3-d][1,3]dioxol-6-yloxy)methyl]-6-chloro-4-phenyl-3-quinolinecarboxylate
• CAS: 1203506-55-1
• 化学式: C₃₁H₃₄ClNO₈
• 分子量: 584.066
• InChiKey: HSKKGLCCYKBXRB-HPTKVVQYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.65
• 重原子数：
  41.0
• 可旋转键数：
  7.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  94.57
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-[((3aR,5R,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethylperhydrofuro[2,3-d][1,3]dioxol-6-yloxy)methyl]-6-chloro-4-phenyl-3-quinolinecarboxylate 在 硫酸 、 水 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以65%的产率得到ethyl 2-[((3aR,5R,6S,6aR)-5-[(1R)-1,2-dihydroxyethyl]-2,2-dimethylperhydrofuro[2,3-d][1,3]dioxol-6-yloxy)methyl]-6-chloro-4-phenyl-3-quinolinecarboxylate
  参考文献：
  名称：

  Diversity-Oriented Synthesis of Quinolines via Friedländer Annulation Reaction under Mild Catalytic Conditions

  摘要：

  An efficient and practical method has been manifested for the diversity-oriented synthesis of quinolines via Friedlander annulation reaction for the generation of a wide range of structurally interesting and pharmacologically significant compounds by using ceric ammonium nitrate as a catalyst (10 mol %) at ambient temperature in 45 min. A variety of functional groups are introduced at various positions of the quinoline moiety, and further the diversity of the core skeleton was expanded at R-1 and R-2 positions by the synthesis of various hybrids. Initial screening of the compounds for cytotoxicity against a series of cancer cell lines showed promising results,

  DOI：

  10.1021/cc900129t
• 作为产物：
  描述：

  ethyl 6-chloro-2-(chloromethyl)-4-phenylquinoline-3-carboxylate 、 双丙酮葡萄糖 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以85%的产率得到ethyl 2-[((3aR,5R,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethylperhydrofuro[2,3-d][1,3]dioxol-6-yloxy)methyl]-6-chloro-4-phenyl-3-quinolinecarboxylate
  参考文献：
  名称：

  Diversity-Oriented Synthesis of Quinolines via Friedländer Annulation Reaction under Mild Catalytic Conditions

  摘要：

  An efficient and practical method has been manifested for the diversity-oriented synthesis of quinolines via Friedlander annulation reaction for the generation of a wide range of structurally interesting and pharmacologically significant compounds by using ceric ammonium nitrate as a catalyst (10 mol %) at ambient temperature in 45 min. A variety of functional groups are introduced at various positions of the quinoline moiety, and further the diversity of the core skeleton was expanded at R-1 and R-2 positions by the synthesis of various hybrids. Initial screening of the compounds for cytotoxicity against a series of cancer cell lines showed promising results,

  DOI：

  10.1021/cc900129t