1-<(5,7-dioxaoct-3-en-4-yl)methyl>-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline | 136587-54-7

• 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: 1-<(5,7-dioxaoct-3-en-4-yl)methyl>-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 1-[(5,7-dioxaoct-3-en-4-yl)methyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
• CAS: 136587-54-7；136587-55-8
• 化学式: C₁₈H₂₇NO₄
• 分子量: 321.417
• InChiKey: MUPGUSKQGVPPEM-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  48.95
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 1-<(5,7-dioxaoct-3-en-4-yl)methyl>-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 在 camphor-10-sulfonic acid 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以61.3%的产率得到11-cis-3-ethyl-9,10-dimethoxy-3,4,6,7-tetrahydro-1H-pyrido[2,1-a]isoquinolin-2(11bH)-one
  参考文献：
  名称：

  Asymmetric synthesis of benzoquinolizidines: a formal synthesis of (-)-emetine

  摘要：

  Chiral formamidines affixed to tetrahydroisoquinoline derivatives affords the appropriate precursor 9 to various benzo[a]quinolizidines 2 and 3 and dibenzo[a,g]quinolizidines 4 in modest to high optical purity. Both 3 and 4 have been utilized in total syntheses of natural emetine 1, thus the route herein constitutes a formal total synthesis of 1. Furthermore, Mannich cyclizations of 1-alkylisoquinolines 18a-c proceeded with or without loss of absolute stereochemistry at the C-1 position. Explanation for this behavior is based upon whether a [3,3] rearrangement or a Mannich reaction takes place. The former results in virtually complete racemization of 18, whereas the latter totally conserves the chirality in 18. Finally, 1-alkynylisoquinolines of high optical purity were transformed, via the Overman protocol, to alkylidine benzo[a]quinolizidines 24 in good yield and to our knowledge, high enantiomeric excess.

  DOI：

  10.1021/jo00024a032
• 作为产物：
  描述：

  1-chloro-2-(methoxymethoxy)pent-2-ene 、 ((S)-1-tert-Butoxymethyl-2-methyl-propyl)-[1-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-meth-(E)-ylidene]-amine 生成 1-<(5,7-dioxaoct-3-en-4-yl)methyl>-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 、 1-<(5,7-dioxaoct-3-en-4-yl)methyl>-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Asymmetric synthesis of benzoquinolizidines: a formal synthesis of (-)-emetine

  摘要：

  Chiral formamidines affixed to tetrahydroisoquinoline derivatives affords the appropriate precursor 9 to various benzo[a]quinolizidines 2 and 3 and dibenzo[a,g]quinolizidines 4 in modest to high optical purity. Both 3 and 4 have been utilized in total syntheses of natural emetine 1, thus the route herein constitutes a formal total synthesis of 1. Furthermore, Mannich cyclizations of 1-alkylisoquinolines 18a-c proceeded with or without loss of absolute stereochemistry at the C-1 position. Explanation for this behavior is based upon whether a [3,3] rearrangement or a Mannich reaction takes place. The former results in virtually complete racemization of 18, whereas the latter totally conserves the chirality in 18. Finally, 1-alkynylisoquinolines of high optical purity were transformed, via the Overman protocol, to alkylidine benzo[a]quinolizidines 24 in good yield and to our knowledge, high enantiomeric excess.

  DOI：

  10.1021/jo00024a032