1,4,8-trimethoxy-3-(2-bromo-4-methyl-6-methoxyphenyl)naphthalene-2-carboxamide | 133129-33-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,4,8-trimethoxy-3-(2-bromo-4-methyl-6-methoxyphenyl)naphthalene-2-carboxamide
• 英文别名: 3-(2-bromo-6-methoxy-4-methylphenyl)-1,4,8-trimethoxynaphthalene-2-carboxamide
• CAS: 133129-33-6
• 化学式: C₂₂H₂₂BrNO₅
• 分子量: 460.324
• InChiKey: RPMIDLOJFIKCHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.71
• 重原子数：
  29.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  80.01
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1,4,8-trimethoxy-3-(2-bromo-4-methyl-6-methoxyphenyl)naphthalene-2-carboxamide 在 叔丁基锂 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 1.0h， 以3%的产率得到tri-O-methylkinafluorenone
  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-(trimethylsilyl)ethyl 1,4,8-trimethoxy-3-(2-bromo-6-methoxy-4-methylphenyl)naphthalene-2-carboxylate 在 吡啶 、 三氟甲磺酸酐 、 四丁基氟化铵 、 氨 作用下， 以 四氢呋喃 为溶剂， 反应 9.0h， 生成 1,4,8-trimethoxy-3-(2-bromo-4-methyl-6-methoxyphenyl)naphthalene-2-carboxamide
  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

• Total synthesis of phenanthroviridin aglycon: the first naturally-occurring benzo[b]phenanthridine
  作者：Makarand P. Gore、Steven J. Gould、Dwight D. Weller

  DOI：10.1021/jo00007a009

  日期：1991.3

  The first synthesis of a naturally occurring benzo[b]phenanthridine has been accomplished via coupling of a cyanophthalide and a substituted bromocinnamate and subsequent transformation of the resulting aryl naphthoquinone carboxylate via formylation, Hoffmann rearrangement, cyclization, and deprotection steps.
• GORE, MAKARAND P.;GOULD, STEVEN J.;WELLER, DWIGHT D., J. ORG. CHEM. , 56,(1991) N, C. 2289-2291
  作者：GORE, MAKARAND P.、GOULD, STEVEN J.、WELLER, DWIGHT D.

  DOI：——

  日期：——
• 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.