2-(trimethylsilyl)ethyl 3-(2-bromo-6-methoxy-4-methylphenyl)-8-methoxy-1,4-naphthoquinone-2-carboxylate | 133129-31-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(trimethylsilyl)ethyl 3-(2-bromo-6-methoxy-4-methylphenyl)-8-methoxy-1,4-naphthoquinone-2-carboxylate
• 英文别名: 2-trimethylsilylethyl 3-(2-bromo-6-methoxy-4-methylphenyl)-8-methoxy-1,4-dioxonaphthalene-2-carboxylate
• CAS: 133129-31-4
• 化学式: C₂₅H₂₇BrO₆Si
• 分子量: 531.475
• InChiKey: HGUZGNAULLQCDN-UHFFFAOYSA-N

物化性质

• 沸点：
  629.8±55.0 °C(Predicted)
• 密度：
  1.320±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.49
• 重原子数：
  33.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  78.9
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-(trimethylsilyl)ethyl 3-(2-bromo-6-methoxy-4-methylphenyl)-8-methoxy-1,4-naphthoquinone-2-carboxylate 在 吡啶 、 sodium dithionite 、 三氟甲磺酸酐 、 四丁基氟化铵 、 氨 、 叔丁基锂 、 potassium carbonate 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 24.0h， 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：

  Total synthesis of phenanthroviridin aglycon: the first naturally-occurring benzo[b]phenanthridine

  摘要：

  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.

  DOI：

  10.1021/jo00007a009
• 作为产物：
  描述：

  2-(三甲硅基)乙醇 在 正丁基锂 、 氧气 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 54.0h， 生成 2-(trimethylsilyl)ethyl 3-(2-bromo-6-methoxy-4-methylphenyl)-8-methoxy-1,4-naphthoquinone-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

• 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：——
• 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.
• 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.