2-(4-benzyloxy-3-methoxyphenacyl)pyrrolidine | 78178-74-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(4-benzyloxy-3-methoxyphenacyl)pyrrolidine
• 英文别名: 4-benzyloxy-3-methoxy-ω-pyrrolidin-2-ylacetophenone；4'-benzyloxy-3'-methoxy-2-pyrrolidin-2-ylacetophenone；1-(3-methoxy-4-phenylmethoxyphenyl)-2-pyrrolidin-2-ylethanone
• CAS: 78178-74-2
• 化学式: C₂₀H₂₃NO₃
• 分子量: 325.408
• InChiKey: DLKDNMUFKIUASB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  47.56
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  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， 生成 7-(4-Benzyloxy-3-methoxy-phenyl)-6-(3,4-bis-benzyloxy-phenyl)-2,3,8,8a-tetrahydro-1H-indolizin-5-one
  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：

  ethyl (4-benzyloxy-3-methoxybenzoyl)acetate 以 甲醇 、 水 为溶剂， 生成 2-(4-benzyloxy-3-methoxyphenacyl)pyrrolidine
  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

文献信息

• Herbert, Richard B.; Jackson, Frederick B.; Nicolson, Ian T., Journal of the Chemical Society. Perkin transactions I, 1984, # 4, p. 825 - 831
  作者：Herbert, Richard B.、Jackson, Frederick B.、Nicolson, Ian T.

  DOI：——

  日期：——
• Herbert, Richard B.; Wormald, Peter C., Journal of Chemical Research, Miniprint, 1982, # 11, p. 3001 - 3010
  作者：Herbert, Richard B.、Wormald, Peter C.

  DOI：——

  日期：——
• IWASA, KINUKO;KAMIGAUCHI, MIYOKO;TAKAO, NARAO;WIEGREBE, WOLFGANG, J. NATUR. PROD., 51,(1988) N 1, 172-175
  作者：IWASA, KINUKO、KAMIGAUCHI, MIYOKO、TAKAO, NARAO、WIEGREBE, WOLFGANG

  DOI：——

  日期：——
• Biosynthesis of tylophorine and tylophorinine
  作者：Dewan S. Bhakuni、Virendra K. Mangla

  DOI：10.1016/s0040-4020(01)92028-9

  日期：1981.1

  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).