methyl 1,4,8-trimethoxy-3-(2-methoxy-4-methylphenyl)naphthalene-2-carboxylate | 139976-09-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl 1,4,8-trimethoxy-3-(2-methoxy-4-methylphenyl)naphthalene-2-carboxylate
• CAS: 139976-09-3
• 化学式: C₂₃H₂₄O₆
• 分子量: 396.44
• InChiKey: QDYYWZTUMDMAGI-UHFFFAOYSA-N

物化性质

• 沸点：
  513.7±50.0 °C(Predicted)
• 密度：
  1.169±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 1,4,8-trimethoxy-3-(2-methoxy-4-methylphenyl)naphthalene-2-carboxylate 在 氯化亚砜 、 potassium tert-butylate 、 氨 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 44.75h， 生成 2-萘甲酰胺,1,4,8-三甲氧基-3-(2-甲氧基-4-甲基苯基)-
  参考文献：
  名称：

  Synthesis of putative intermediates in the biosynthesis of the kinamycin antibiotics: total synthesis of phenanthroviridin aglycon and related compounds

  摘要：

  Phenanthroviridin aglycon, 14, recently isolated from Streptomyces viridiochromogenes DSM 3972, and the corresponding pyridone 10 have been synthesized from the common intermediate (bromoaryl)naphthamide 42. This was prepared by condensation of a (trimethylsilyl)ethyl (bromoaryl)cinnamate 36 and a methoxy-substituted cyanophthalide anion 15, providing the ABD rings of the target benzo[b]phenanthridine skeleton. The aglycon 14 was obtained by a sequence of metal-halogen exchange and formylation, Hofmann rearrangement, cyclization, and deprotection. The pyridone was obtained by Hofmann rearrangement, metal-halogen exchange, cyclization, and deprotection. In addition, a route to cinnamate 36 via coumarin 49 was developed which would allow selective protection of the 1-hydroxyl group for synthesis of glycosidic analogues of phenanthroviridin, 13. The methodology developed is useful for preparation of 10, 14, and analogues specifically labeled at C-5 for study of biosynthesis of the kinamycin antibiotics.

  DOI：

  10.1021/jo00036a005
• 作为产物：
  描述：

  2-甲氧基-4-甲基苯甲醛 在 哌啶 、 吡啶 、 sodium dithionite 、 potassium carbonate 、 lithium diisopropyl amide 作用下， 以 乙醚 、 丙酮 为溶剂， 反应 31.25h， 生成 methyl 1,4,8-trimethoxy-3-(2-methoxy-4-methylphenyl)naphthalene-2-carboxylate
  参考文献：
  名称：

  Synthesis of putative intermediates in the biosynthesis of the kinamycin antibiotics: total synthesis of phenanthroviridin aglycon and related compounds

  摘要：

  Phenanthroviridin aglycon, 14, recently isolated from Streptomyces viridiochromogenes DSM 3972, and the corresponding pyridone 10 have been synthesized from the common intermediate (bromoaryl)naphthamide 42. This was prepared by condensation of a (trimethylsilyl)ethyl (bromoaryl)cinnamate 36 and a methoxy-substituted cyanophthalide anion 15, providing the ABD rings of the target benzo[b]phenanthridine skeleton. The aglycon 14 was obtained by a sequence of metal-halogen exchange and formylation, Hofmann rearrangement, cyclization, and deprotection. The pyridone was obtained by Hofmann rearrangement, metal-halogen exchange, cyclization, and deprotection. In addition, a route to cinnamate 36 via coumarin 49 was developed which would allow selective protection of the 1-hydroxyl group for synthesis of glycosidic analogues of phenanthroviridin, 13. The methodology developed is useful for preparation of 10, 14, and analogues specifically labeled at C-5 for study of biosynthesis of the kinamycin antibiotics.

  DOI：

  10.1021/jo00036a005

文献信息

• Identification of Prekinamycin in Extracts of <i>Streptomyces murayamaensis</i>
  作者：Steven J. Gould、Jiong Chen、Martha C. Cone、Makarand P. Gore、Chris R. Melville、Nuria Tamayo

  DOI：10.1021/jo9611024

  日期：1996.1.1
• Synthesis of putative intermediates in the biosynthesis of the kinamycin antibiotics: total synthesis of phenanthroviridin aglycon and related compounds
  作者：Makarand P. Gore、Steven J. Gould、Dwight D. Weller

  DOI：10.1021/jo00036a005

  日期：1992.5

  Phenanthroviridin aglycon, 14, recently isolated from Streptomyces viridiochromogenes DSM 3972, and the corresponding pyridone 10 have been synthesized from the common intermediate (bromoaryl)naphthamide 42. This was prepared by condensation of a (trimethylsilyl)ethyl (bromoaryl)cinnamate 36 and a methoxy-substituted cyanophthalide anion 15, providing the ABD rings of the target benzo[b]phenanthridine skeleton. The aglycon 14 was obtained by a sequence of metal-halogen exchange and formylation, Hofmann rearrangement, cyclization, and deprotection. The pyridone was obtained by Hofmann rearrangement, metal-halogen exchange, cyclization, and deprotection. In addition, a route to cinnamate 36 via coumarin 49 was developed which would allow selective protection of the 1-hydroxyl group for synthesis of glycosidic analogues of phenanthroviridin, 13. The methodology developed is useful for preparation of 10, 14, and analogues specifically labeled at C-5 for study of biosynthesis of the kinamycin antibiotics.