(-)-protoberberine | 59373-39-6

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 原小檗碱生物碱及其衍生物
• 英文名称: (-)-protoberberine
• 英文别名: rel-(13R,13aR)-5,8,13,13a-Tetrahydro-2,3,10,11-tetramethoxy-6H-dibenzo[a,g]quinolizin-13-ol；(13R,13aR)-2,3,10,11-tetramethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinolin-13-ol
• CAS: 59373-39-6
• 化学式: C₂₁H₂₅NO₅
• 分子量: 371.433
• InChiKey: GJYZSDLAHXVPNH-NHCUHLMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  60.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (-)-protoberberine 在 吡啶 、 lithium aluminium tetrahydride 、 氯化亚砜 作用下， 生成 (-)-番荔枝宁
  参考文献：
  名称：

  Asymmetric Synthesis of Isoquinoline Alkaloids: (R)- and (S)-2-Ethoxycarbonyl-1-Formyl-6, 7-Dimethoxy-1,2,3,4-Tetrahydroisoquinoline as Versatile Precursors

  摘要：

  AbstractA method is described for the preparation of (R)‐ and (S)‐2‐ethoxycarbonyl‐1‐formyl‐6,7‐dimethoxy‐1,2,3,4‐tetrahydroisoquinoline involving a Swerntype oxidation of (R)‐ and (S)‐2‐ethoxycarbonyl‐1‐hydroxymethyl‐6, 7‐dimethoxy‐1,2,3,4‐tetrahydroisoquinoline {(R)‐ and (S)‐2‐(ethoxycarbonyl)calycotomine}. The utility of these aldehydes in asymmetric synthesis of isoquinoline alkaloids has been demonstrated by their conversion into (S)‐ and (R)‐xylopinine, respectively; also, the (R)‐aldehyde has been employed for the synthesis of (8S,14S)‐coralydine.

  DOI：

  10.1002/bscb.19860950905
• 作为产物：
  描述：

  (+)-threo-N-(ethoxycarbonyl)hydroxynorlaudanosine 在 盐酸 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 6.0h， 生成 (-)-protoberberine
  参考文献：
  名称：

  Asymmetric Synthesis of Isoquinoline Alkaloids: (R)- and (S)-2-Ethoxycarbonyl-1-Formyl-6, 7-Dimethoxy-1,2,3,4-Tetrahydroisoquinoline as Versatile Precursors

  摘要：

  AbstractA method is described for the preparation of (R)‐ and (S)‐2‐ethoxycarbonyl‐1‐formyl‐6,7‐dimethoxy‐1,2,3,4‐tetrahydroisoquinoline involving a Swerntype oxidation of (R)‐ and (S)‐2‐ethoxycarbonyl‐1‐hydroxymethyl‐6, 7‐dimethoxy‐1,2,3,4‐tetrahydroisoquinoline {(R)‐ and (S)‐2‐(ethoxycarbonyl)calycotomine}. The utility of these aldehydes in asymmetric synthesis of isoquinoline alkaloids has been demonstrated by their conversion into (S)‐ and (R)‐xylopinine, respectively; also, the (R)‐aldehyde has been employed for the synthesis of (8S,14S)‐coralydine.

  DOI：

  10.1002/bscb.19860950905

文献信息

• Asymmetric Synthesis of Isoquinoline Alkaloids: (R)- and (S)-2-Ethoxycarbonyl-1-Formyl-6, 7-Dimethoxy-1,2,3,4-Tetrahydroisoquinoline as Versatile Precursors
  作者：Zbigniew Czarnocki、David B. Maclean、Walter A. Szarek

  DOI：10.1002/bscb.19860950905

  日期：——

  AbstractA method is described for the preparation of (R)‐ and (S)‐2‐ethoxycarbonyl‐1‐formyl‐6,7‐dimethoxy‐1,2,3,4‐tetrahydroisoquinoline involving a Swerntype oxidation of (R)‐ and (S)‐2‐ethoxycarbonyl‐1‐hydroxymethyl‐6, 7‐dimethoxy‐1,2,3,4‐tetrahydroisoquinoline (R)‐ and (S)‐2‐(ethoxycarbonyl)calycotomine}. The utility of these aldehydes in asymmetric synthesis of isoquinoline alkaloids has been demonstrated by their conversion into (S)‐ and (R)‐xylopinine, respectively; also, the (R)‐aldehyde has been employed for the synthesis of (8S,14S)‐coralydine.