2-hydroxy-3-methoxy-12-vinyl-5,6-dihydro-8H-isoquino[2,1-b][2,7]naphthyridin-8-one | 77156-16-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2-hydroxy-3-methoxy-12-vinyl-5,6-dihydro-8H-isoquino[2,1-b][2,7]naphthyridin-8-one
• 英文别名: alangimarine；12-ethenyl-2-hydroxy-3-methoxy-5,6-dihydroisoquinolino[2,1-b][2,7]naphthyridin-8-one
• CAS: 77156-16-2
• 化学式: C₁₉H₁₆N₂O₃
• 分子量: 320.348
• InChiKey: JWOCTFIJQXTYOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  62.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-hydroxy-3-methoxy-12-vinyl-5,6-dihydro-8H-isoquino[2,1-b][2,7]naphthyridin-8-one 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 dihydroalangimarine
  参考文献：
  名称：

  Lamarckii Thw产的新型苯并吡啶并喹啉嗪碱。

  摘要：

  从标题植物的种子中分离出的Alangimarine（1），alamarine（2）和alangimaridine（3）被表征为一类新的生物碱。指出茎皮中存在异阿拉莫林（13）。

  DOI：

  10.1016/s0040-4039(00)92835-1
• 作为产物：
  描述：

  alangiside 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 6481.0h， 生成 2-hydroxy-3-methoxy-12-vinyl-5,6-dihydro-8H-isoquino[2,1-b][2,7]naphthyridin-8-one
  参考文献：
  名称：

  Isolation of Two Unusual Tetrahydroisoquinoline-Monoterpene Glucosides from Alangium lamarckii as Possible Intermediates in the Non-enzymatic Formation of Alangimarine from Alangiside

  摘要：

  From the fruits of Alangium lamarckii, two new glucosides (3) and (4), which possessed unusual structures different from any known tetrahydro-isoquinoline-monoterpene glucosides, have been isolated. Their structures were determined on the basis of spectroscopic and chemical methods. These same glucosides were also obtained by storage of alangiside (2) in MeOH for a prolonged period and glucoside (4) was further converted to alangimarine (1), a benzopyridoquinolizine alkaloid from this plant, by the usual treatment for isolation of alkaloids, suggesting the possibility of non-enzymatic formation of alangimarine (1) from alangiside (2) via the isolated glucosides (3) and (4).

  DOI：

  10.3987/com-97-8069

文献信息

• Activated imines as carbon electrophiles: applications in alkaloid synthesis
  作者：Jahangir、David B. MacLean、Michael A. Brook、Herbert L. Holland

  DOI：10.1039/c39860001608

  日期：——

  react with trimethylsilyl trifluoromethanesulphonate to form complexes that react readily with the lithio derivatives of 3-cyano-4-methylpyridines; the method has been applied to the synthesis of the Alangium alkaloids, (±)-alangimaridine and alangimarine.

  3，4-二氢异喹啉和3，4-二氢-β-咔啉与三氟甲磺酸三甲基甲硅烷基酯反应形成易于与3-氰基-4-甲基吡啶的硫代衍生物反应的络合物。该方法已用于合成Alangium生物碱，（±）-alangimaridine和alangimarine。
• Brook, Jahangir Michael A.; MacLean, David B.; Holland, Herbert L., Canadian Journal of Chemistry, 1987, vol. 65, p. 2362 - 2368
  作者：Brook, Jahangir Michael A.、MacLean, David B.、Holland, Herbert L.

  DOI：——

  日期：——
• JAHANGIR;BROOK, MICHAEL A.;MACLEAN, DAVID B.;HOLLAND, HERBERT L., CAN. J. CHEM., 65,(1987) N 10, 2362-2368
  作者：JAHANGIR、BROOK, MICHAEL A.、MACLEAN, DAVID B.、HOLLAND, HERBERT L.

  DOI：——

  日期：——
• Pakrashi, S. C.; Mukhopadhyay, R.; Sinha, R. R., Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1985, vol. 24, p. 19 - 28
  作者：Pakrashi, S. C.、Mukhopadhyay, R.、Sinha, R. R.、Dastidar, P. P. Ghosh、Achari, B.、Ali, E.

  DOI：——

  日期：——
• Isolation of Two Unusual Tetrahydroisoquinoline-Monoterpene Glucosides from Alangium lamarckii as Possible Intermediates in the Non-enzymatic Formation of Alangimarine from Alangiside
  作者：Atsuko Itoh、Takao Tanahashi、Naotaka Nagakura

  DOI：10.3987/com-97-8069

  日期：——

  From the fruits of Alangium lamarckii, two new glucosides (3) and (4), which possessed unusual structures different from any known tetrahydro-isoquinoline-monoterpene glucosides, have been isolated. Their structures were determined on the basis of spectroscopic and chemical methods. These same glucosides were also obtained by storage of alangiside (2) in MeOH for a prolonged period and glucoside (4) was further converted to alangimarine (1), a benzopyridoquinolizine alkaloid from this plant, by the usual treatment for isolation of alkaloids, suggesting the possibility of non-enzymatic formation of alangimarine (1) from alangiside (2) via the isolated glucosides (3) and (4).