原荷叶碱 | 2128-60-1

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 阿朴啡原
• 中文名称: 原荷叶碱
• 英文名称: pronuciferine
• 英文别名: Pronuciferin；(+)-Pronuciferine；(4R)-10,11-dimethoxy-5-methylspiro[5-azatricyclo[6.3.1.04,12]dodeca-1(12),8,10-triene-2,4'-cyclohexa-2,5-diene]-1'-one
• CAS: 2128-60-1
• 化学式: C₁₉H₂₁NO₃
• mdl: MFCD01119101
• 分子量: 311.381
• InChiKey: WUYQEGNOQLRQAQ-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (-)-N-formylstepharine 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 2.0h， 生成 原荷叶碱
  参考文献：
  名称：

  Alkaloids of Caryomene olivascens (Menispermaceae). Bisbenzylisoquinoline with new structure.

  摘要：

  Nine isoquinoline alkaloids belonging to the protoberberine, proaporphine and bisbenzyl-isoquinoline series were isolated from Caryomene olivascens (Menispermaceae). Four compounds are new : (-)-2-norlimacine (4), (-)-caryolivine (6), (+)-1, 2-dehydro-2-norlimacusine (9) and N-formylstepharine (3). The last one is the first N-formyl derivative to be reported in the proaporphine group. Its biogenetic origin is discussed. Structures were established on the basis of 360 MHz (FT) nuclear magnetic resonance measurements and also by chemical correlation in the case of 3.

  DOI：

  10.1248/cpb.34.1148

文献信息

• Alkaloids of Caryomene olivascens (Menispermaceae). Bisbenzylisoquinoline with new structure.
  作者：MARIE LAVAULT、ALAIN FOURNET、HELENE GUINAUDEAU、JEAN BRUNETON

  DOI：10.1248/cpb.34.1148

  日期：——

  Nine isoquinoline alkaloids belonging to the protoberberine, proaporphine and bisbenzyl-isoquinoline series were isolated from Caryomene olivascens (Menispermaceae). Four compounds are new : (-)-2-norlimacine (4), (-)-caryolivine (6), (+)-1, 2-dehydro-2-norlimacusine (9) and N-formylstepharine (3). The last one is the first N-formyl derivative to be reported in the proaporphine group. Its biogenetic origin is discussed. Structures were established on the basis of 360 MHz (FT) nuclear magnetic resonance measurements and also by chemical correlation in the case of 3.