ethyl (6R,7R)-7-(hydroxymethyl)-5-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]quinoline-6-carboxylate | 1448019-85-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl (6R,7R)-7-(hydroxymethyl)-5-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]quinoline-6-carboxylate
• 英文别名: ethyl (6R,7R)-7-(hydroxymethyl)-5-(3,4,5-trimethoxyphenyl)-7,8-dihydro-6H-[1,3]dioxolo[4,5-g]quinoline-6-carboxylate
• CAS: 1448019-85-9
• 化学式: C₂₃H₂₇NO₈
• 分子量: 445.469
• InChiKey: DRMXRFHBOQKXOQ-LHSJRXKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  95.9
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  ethyl (6R,7R)-7-{[(tert-butyldimethylsilyl)oxy]methyl}-5-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]quinoline-6-carboxylate 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 aq. phosphate buffer 为溶剂， 反应 36.0h， 以74%的产率得到ethyl (6R,7R)-7-(hydroxymethyl)-5-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]quinoline-6-carboxylate
  参考文献：
  名称：

  Asymmetric Synthesis of 1-Aza-4-deoxypicropodophyllotoxin

  摘要：

  In our search for new easily accessible analogues based on the natural product podophyllotoxin, we synthesized 1-aza-4-deoxypicropodophyllotoxin in good overall yield and excellent enantioselectivity. The synthesis was centered around a direct asymmetric Mannich reaction using D-proline as the key step for introduction of the chiral centres. Our synthesis of 1-aza-4-deoxypodophyllotoxin was hindered through the increased instability towards epimerization of the C2 position. We did, however, synthesized a new scaffold based on the opened lactone analogue.

  DOI：

  10.1055/s-0033-1338414