6-(3-benzyloxy-4-methoxyphenyl)-7-(4-benzyloxy-3-methoxyphenyl)-5-oxo-1,2,3,5,8,8a-hexahydroindolizine | 78278-47-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 6-(3-benzyloxy-4-methoxyphenyl)-7-(4-benzyloxy-3-methoxyphenyl)-5-oxo-1,2,3,5,8,8a-hexahydroindolizine
• CAS: 78278-47-4
• 化学式: C₃₆H₃₅NO₅
• 分子量: 561.678
• InChiKey: LUVNCUAZQGMTJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.17
• 重原子数：
  42.0
• 可旋转键数：
  10.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  57.23
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  6-(3-benzyloxy-4-methoxyphenyl)-7-(4-benzyloxy-3-methoxyphenyl)-5-oxo-1,2,3,5,8,8a-hexahydroindolizine 在 lithium aluminium tetrahydride 、 三氯化铝 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 以162 mg的产率得到6-(3-benzyloxy-4-methoxy)-7-(4-benzyloxy-3-methoxyphenyl)-1,2,3,5,8,8a-hexahydroindolizine
  参考文献：
  名称：

  Biosynthesis of tylophorine and tylophorinine

  摘要：

  Administration of 3,4-dihydroxyphenyl[2-14C]alanine to young Tylophora asthmatica plants revealed that ring B and carbon atoms C9 and C7 of tylophorine and tylophorinine [phenanthroin dolizidine alkaloids] are derived from dopa. Tracer experiments with 6,7-diphenylhexahydroindolizines (1-7) and (26) demonstrated that compound 1 is efficiently and specifically incorporated into tylophorine (13) and tylophorinine (16). Compounds (3), (4) and (26) were not metabolized by the plants to form (13) and (16) whereas (5) and (6) were utilized to yield (13) and (16). Compound (2) was very poorly converted into (13) and (16) and thus is not on the major biosynthetic pathway of (13) and (16).

  DOI：

  10.1016/s0040-4020(01)92028-9
• 作为产物：
  描述：

  2-(4-benzyloxy-3-methoxyphenacyl)pyrrolidine 在 吡啶 、 氢氧化钾 作用下， 以 乙醇 、 苯 为溶剂， 反应 23.0h， 生成 6-(3-benzyloxy-4-methoxyphenyl)-7-(4-benzyloxy-3-methoxyphenyl)-5-oxo-1,2,3,5,8,8a-hexahydroindolizine
  参考文献：
  名称：

  Biosynthesis of tylophorine and tylophorinine

  摘要：

  Administration of 3,4-dihydroxyphenyl[2-14C]alanine to young Tylophora asthmatica plants revealed that ring B and carbon atoms C9 and C7 of tylophorine and tylophorinine [phenanthroin dolizidine alkaloids] are derived from dopa. Tracer experiments with 6,7-diphenylhexahydroindolizines (1-7) and (26) demonstrated that compound 1 is efficiently and specifically incorporated into tylophorine (13) and tylophorinine (16). Compounds (3), (4) and (26) were not metabolized by the plants to form (13) and (16) whereas (5) and (6) were utilized to yield (13) and (16). Compound (2) was very poorly converted into (13) and (16) and thus is not on the major biosynthetic pathway of (13) and (16).

  DOI：

  10.1016/s0040-4020(01)92028-9