2-methoxy-5-(4'-methoxyphenyl)cyclohepta-2,4,6-trien-1-one | 107752-76-1

• 分子结构分类: 有机化合物 - 碳氢化合物衍生物 - 环庚三烯酮
• 英文名称: 2-methoxy-5-(4'-methoxyphenyl)cyclohepta-2,4,6-trien-1-one
• 英文别名: 2-Methoxy-5-(4-methoxyphenyl)cyclohepta-2,4,6-trien-1-one
• CAS: 107752-76-1
• 化学式: C₁₅H₁₄O₃
• 分子量: 242.274
• InChiKey: KOYAXJLDPCYFBK-UHFFFAOYSA-N

物化性质

• 熔点：
  148.5-148.9 °C
• 沸点：
  450.2±45.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 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：

  2-methoxy-5-(4'-methoxyphenyl)cyclohepta-2,4,6-trien-1-one 、 氢氧化钾 生成 5-(4-methoxyphenyl)tropolone
  参考文献：
  名称：

  NOZOE TETSUO; TAKASE KAHEI; SAITO HIROAKI; YAMAMOTO HIROSHI; IMAFUKU KIMI+, CHEM. LETT.,(1986) N 9, 1577-1580

  摘要：

  DOI：
• 作为产物：
  描述：

  (4-methoxyphenyl)trimethylstannane 在 bis-triphenylphosphine-palladium(II) chloride potassium carbonate 作用下， 以 1,4-二氧六环 、 丙酮 为溶剂， 反应 7.0h， 生成 2-methoxy-5-(4'-methoxyphenyl)cyclohepta-2,4,6-trien-1-one
  参考文献：
  名称：

  Banwell, Martin G.; Cameron, Jennifer M.; Collis, Maree P., Australian Journal of Chemistry, 1991, vol. 44, # 5, p. 705 - 728

  摘要：

  DOI：

文献信息

• A Convenient Synthesis of 5-Aryltropolones via Novel Benzidine Type Rearrangement of 2-(2-Arylhydrazino)tropones
  作者：Tetsuo Nozoe、Kahei Takase、Hiroaki Saito、Hiroshi Yamamoto、Kimiaki Imafuku

  DOI：10.1246/cl.1986.1577

  日期：1986.9.5

  Treatment of a wide variety of 2-(2-arylhydrazino)tropones with ethanolic acid at 50–80 °C readily gave the benzidine type rearrangement products, i.e. 2-amino-5-(4-aminoaryl)tropones, which in turn were conveniently led to the corresponding 5-aryltropolones that can be utilized for synthesizing B-ring-open analogues of colchicine.

  在 50–80 °C 下用乙醇酸处理各种 2-(2-芳基肼基) 托酮很容易得到联苯胺型重排产物，即 2-氨基-5-(4-氨基芳基)托酮，这反过来又很方便导致相应的 5-芳基托酚酮可用于合成秋水仙碱的 B 环开环类似物。
• Efforts Directed toward the Synthesis of Colchicine:  Application of Palladium-Catalyzed Siloxane Cross-Coupling Methodology
  作者：W. Michael Seganish、Christopher J. Handy、Philip DeShong

  DOI：10.1021/jo051636h

  日期：2005.10.1

  Colchicine is an important and synthetically challenging natural product. The key synthetic step in this approach to the synthesis of colchicine involved a palladium-catalyzed cross-coupling reaction between 5-bromotropolone (4) and an aryl siloxane to form the aryl-tropolone bond. The coupling of a variety of highly functionalized aryl siloxane derivatives was investigated and optimized coupling conditions were developed. It was discovered that a palladium catalyst with a high degree of phosphine ligand coordination (5 equiv of phosphine/mol Pd) was necessary to efficiently couple aryl siloxanes with 5-bromotropolone (4). In addition, the coupling approach has provided a direct comparison between siloxane and boronic acid coupling technologies that demonstrated that aryl siloxanes and boronic acids produce similar yields of highly functionalized biaryl products.
• Nair, Vijay; Powell, Dennis W.; Suri, Suresh Chander, Synthetic Communications, 1987, vol. 17, # 16, p. 1897 - 1900
  作者：Nair, Vijay、Powell, Dennis W.、Suri, Suresh Chander

  DOI：——

  日期：——
• Keenan, Richard M.; Kruse, Lawrence I., Synthetic Communications, 1989, vol. 19, # 5and6, p. 793 - 798
  作者：Keenan, Richard M.、Kruse, Lawrence I.

  DOI：——

  日期：——
• KEENAN, RICHARD M.;KRUSE, LAWRENCE I., SYNTH. COMMUN., 19,(1989) N-6, C. 793-798
  作者：KEENAN, RICHARD M.、KRUSE, LAWRENCE I.

  DOI：——

  日期：——