methyl 2-methoxy-4-methylcinnamate | 139976-02-6

• 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: methyl 2-methoxy-4-methylcinnamate
• 英文别名: Methyl 3-(2-methoxy-4-methylphenyl)prop-2-enoate；methyl 3-(2-methoxy-4-methylphenyl)prop-2-enoate
• CAS: 139976-02-6
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: GLTPFTABPZAJTQ-UHFFFAOYSA-N

物化性质

• 沸点：
  317.5±27.0 °C(Predicted)
• 密度：
  1.081±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 2-methoxy-4-methylcinnamate 在 氢氧化钾 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 26.0h， 生成 2-hydroxy-3-(2-methoxy-4-methylphenyl)-8-methoxy-1,4-naphthoquinone
  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 作用下， 以 乙醚 为溶剂， 反应 4.25h， 生成 methyl 2-methoxy-4-methylcinnamate
  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

• Quinone methide chemistry of prekinamycins: 13C- labeling, spectral global fitting and in vitro studies
  作者：Omar Khdour、Edward B. Skibo

  DOI：10.1039/b903844b

  日期：——

  In this article, we address the presence of the prekinamycin quinone methide using the techniques of spectral global fitting and the13C-labeling of the reactive centre. Two-electron reduction of a prekinamycin affords a long-lived quinone methide species that was characterised spectrally. A correlation was made between the calculated ΔE (kcal/mol) values for quinone methide tautomerisation and cytostatic activity to support the postulate that the quinone methide plays a role in prekinamycin biological activity. We also prepared a stable quinone methide of prekinamycin and studied its solution chemistry directly.

  在这篇文章中，我们利用光谱全局拟合技术和反应中心的 13C 标记技术研究了前激酶醌甲醚的存在。前激纳霉素的双电子还原产生了一种长寿命的醌甲甙物种，并对其进行了光谱表征。计算得出的醌甲醚同分异构化 ΔE（kcal/mol）值与细胞抑制活性之间存在相关性，从而支持了醌甲醚在前激纳霉素生物活性中发挥作用的推测。我们还制备了一种稳定的前激纳霉素醌甲醚，并直接研究了其溶液化学性质。
• 一种制备(R)-3-(2-甲氧基-5-甲基)苯基-3-苯基丙酸甲酯类化合物的方法
  申请人：新乡学院

  公开号：CN114436836B

  公开（公告）日：2023-09-29

  本发明公开了一种制备(R)‑3‑(2‑甲氧基‑5‑甲基)苯基‑3‑苯基丙酸甲酯类化合物的方法，本发明中的方法利用廉价铜催化剂及P,N‑型手性配体的催化作用一步合成(R)‑3‑(2‑甲氧基‑5‑甲基)苯基‑3‑苯基丙酸甲酯类化合物，原料易得，制备方法简单且产率和对映选择性良好；同时催化剂用量少，可大大降低成本。该方法可以作为治疗膀胱过度活动症的药物托特罗定的关键中间体的合成。
• 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.