(S)-2-(ethoxycarbonyl)calycotomine | 109663-58-3

• 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: (S)-2-(ethoxycarbonyl)calycotomine
• 英文别名: ethyl (1S)-1-(hydroxymethyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylate
• CAS: 109663-58-3
• 化学式: C₁₅H₂₁NO₅
• 分子量: 295.335
• InChiKey: TWIPYOWQGSSGGL-GFCCVEGCSA-N

物化性质

• 沸点：
  439.7±45.0 °C(Predicted)
• 密度：
  1.190±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  68.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-2-(ethoxycarbonyl)calycotomine 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 作用下， 生成 (R)-6,7-dimethoxy-1,2-dimethyl-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Asymmetric Intramolecular Allylic Amination: Straightforward Approach to Chiral C1-Substituted Tetrahydroisoquinolines

  摘要：

  新近引入的钯催化不对称分子内烯丙基胺化反应为制药领域重要的1-取代四氢异喹啉类化合物提供了便捷合成途径。以此胺化反应作为关键步骤，（R）-卡尼吉碱得以通过手性选择性合成方法合成。

  DOI：

  10.1055/s-2003-41502
• 作为产物：
  描述：

  (6,7-二甲氧基-1,2,3,4-四氢-异喹啉-1-基)-甲醇 在 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 0.5h， 生成 (S)-2-(ethoxycarbonyl)calycotomine
  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.
• Asymmetric Intramolecular Allylic Amination: Straightforward Approach to Chiral C1-Substituted Tetrahydroisoquinolines
  作者：Katsuji Ito、Tsutomu Katsuki、Suemi Akashi、Bunnai Saito

  DOI：10.1055/s-2003-41502

  日期：——

  Newly introduced Pd-catalyzed asymmetric intra­molecular allylic amination provides an easy access to pharmaceutically important 1-substituted tetrahydroisoquinolines. With this aminatio­n as the key step, (R)-carnegine was synthesized in an enantio­selective manner.

  新近引入的钯催化不对称分子内烯丙基胺化反应为制药领域重要的1-取代四氢异喹啉类化合物提供了便捷合成途径。以此胺化反应作为关键步骤，（R）-卡尼吉碱得以通过手性选择性合成方法合成。