(3R,4S,4aR,11bR)-3,4-dihydroxy-5-[(4-methoxyphenyl)methyl]-3,4,4a,11b-tetrahydro-[1,3]dioxolo[4,5-j]phenanthridin-6-one | 181225-12-7

• 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: (3R,4S,4aR,11bR)-3,4-dihydroxy-5-[(4-methoxyphenyl)methyl]-3,4,4a,11b-tetrahydro-[1,3]dioxolo[4,5-j]phenanthridin-6-one
• CAS: 181225-12-7
• 化学式: C₂₂H₂₁NO₆
• 分子量: 395.412
• InChiKey: TUTQTKXUDBUHHO-HZNDTHDVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  88.5
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3R,4S,4aR,11bR)-3,4-dihydroxy-5-[(4-methoxyphenyl)methyl]-3,4,4a,11b-tetrahydro-[1,3]dioxolo[4,5-j]phenanthridin-6-one 在 phosphate buffer 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以46%的产率得到(2R,3R,5S,6S,7S,8R)-6,7-dihydroxy-9-[(4-methoxyphenyl)methyl]-4,14,16-trioxa-9-azapentacyclo[9.7.0.02,8.03,5.013,17]octadeca-1(18),11,13(17)-trien-10-one
  参考文献：
  名称：

  Total Synthesis of (+)-7-Deoxypancratistatin and (+)-7-Deoxy-trans-dihydronarciclasine

  摘要：

  The chiral and stereoselective synthesis of antimitotic phenanthridone alkaloids, (+)-7-deoxypancratistatin (1) and (+)-7-deoxy-trans-dihydronarciclasine (2) is described. Both natural products were synthesized from the common compound (4), which had been prepared from D-glucose and employed for the synthesis of lycoricidine (3).

  DOI：

  10.3987/com-96-7481
• 作为产物：
  描述：

  [(2S,3R,4S,4aR,11bR)-3,4-bis(methoxymethoxy)-5-[(4-methoxyphenyl)methyl]-6-oxo-1,2,3,4,4a,11b-hexahydro-[1,3]dioxolo[4,5-j]phenanthridin-2-yl] acetate 在 盐酸 、 sodium methylate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 二氯甲烷 为溶剂， 生成 (3R,4S,4aR,11bR)-3,4-dihydroxy-5-[(4-methoxyphenyl)methyl]-3,4,4a,11b-tetrahydro-[1,3]dioxolo[4,5-j]phenanthridin-6-one
  参考文献：
  名称：

  Total Synthesis of (+)-7-Deoxypancratistatin and (+)-7-Deoxy-trans-dihydronarciclasine

  摘要：

  The chiral and stereoselective synthesis of antimitotic phenanthridone alkaloids, (+)-7-deoxypancratistatin (1) and (+)-7-deoxy-trans-dihydronarciclasine (2) is described. Both natural products were synthesized from the common compound (4), which had been prepared from D-glucose and employed for the synthesis of lycoricidine (3).

  DOI：

  10.3987/com-96-7481