2-(trimethylsilyl)ethyl 3-(2-bromo-6-methoxy-4-methyl) cinnamate | 139976-16-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 2-(trimethylsilyl)ethyl 3-(2-bromo-6-methoxy-4-methyl) cinnamate
• CAS: 139976-16-2
• 化学式: C₁₆H₂₃BrO₃Si
• 分子量: 371.346
• InChiKey: ZUTHBQNFFOLMFO-UHFFFAOYSA-N

物化性质

• 沸点：
  424.3±45.0 °C(Predicted)
• 密度：
  1.203±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.66
• 重原子数：
  21.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-(trimethylsilyl)ethyl 3-(2-bromo-6-methoxy-4-methyl) cinnamate 在 sodium dithionite 、 氧气 、 potassium carbonate 、 lithium diisopropyl amide 作用下， 以 丙酮 为溶剂， 反应 72.0h， 生成 2-(trimethylsilyl)ethyl 1,4,8-trimethoxy-3-(2-bromo-6-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
• 作为产物：
  描述：

  2-溴-6-羟基-4-甲基苯甲醛 在 正丁基锂 、 potassium acetate 、 potassium carbonate 作用下， 以 四氢呋喃 、 正己烷 、 丙酮 为溶剂， 反应 9.0h， 生成 2-(trimethylsilyl)ethyl 3-(2-bromo-6-methoxy-4-methyl) cinnamate
  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