(+)-threo-N-(ethoxycarbonyl)hydroxynorlaudanosine | 106647-99-8

• 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-N-(ethoxycarbonyl)hydroxynorlaudanosine
• 英文别名: (-)-threo-N-(ethoxycarbonyl)hydroxynorlaudanosine；(+/-)-erythro-N-(ethoxycarbonyl)hydroxynorlaudanosine
• CAS: 106647-99-8；106756-90-5；109717-72-8；109717-81-9
• 化学式: C₂₃H₂₉NO₇
• 分子量: 431.486
• InChiKey: OLJZFHGOZDDMPX-YADHBBJMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.51
• 重原子数：
  31.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  86.69
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (+)-threo-N-(ethoxycarbonyl)hydroxynorlaudanosine 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以92%的产率得到阿特拉库铵杂质19
  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：

  ethyl 1-formyl-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylate 、 (3,4-二甲氧基苯基)锂 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.17h， 以7.9%的产率得到(+)-threo-N-(ethoxycarbonyl)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