(+)-threo-(O,N-diacetyl)hydroxynorlaudanosine | 109717-75-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: (+)-threo-(O,N-diacetyl)hydroxynorlaudanosine
• CAS: 109717-75-1
• 化学式: C₂₄H₂₉NO₇
• 分子量: 443.497
• InChiKey: RSTWAABLANNIRJ-DNQXCXABSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.47
• 重原子数：
  32.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  83.53
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (+)-threo-(O,N-diacetyl)hydroxynorlaudanosine 在 吡啶 、 sodium hydroxide 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 氯化亚砜 、 三氯氧磷 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 21.03h， 生成 coralydine
  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 sodium hydroxide 作用下， 以 吡啶 、 乙醇 为溶剂， 反应 3.0h， 生成 (+)-threo-(O,N-diacetyl)hydroxynorlaudanosine
  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