4,7-dimethyl-8-methoxycoumarin | 77869-48-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 4,7-dimethyl-8-methoxycoumarin
• 英文别名: 8-Methoxy-4,7-dimethylchromen-2-one
• CAS: 77869-48-8
• 化学式: C₁₂H₁₂O₃
• 分子量: 204.225
• InChiKey: JOVHXMCCSQACMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• 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：

  4,7-dimethyl-8-methoxycoumarin 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 100.0 ℃ 、620.52 kPa 条件下， 反应 4.0h， 以70%的产率得到(+/-)-3,4-dihydro-8-methoxy-4,7-dimethylcoumarin
  参考文献：
  名称：

  Mills, Frank D., Journal of Heterocyclic Chemistry, 1980, vol. 17, p. 1597 - 1600

  摘要：

  DOI：
• 作为产物：
  描述：

  3-甲基苯邻二酚 在 硫酸 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 19.0h， 生成 4,7-dimethyl-8-methoxycoumarin
  参考文献：
  名称：

  A new approach to the pseudopterosins using an arene alkylation with a γ-methylene-γ-butyrolactone

  摘要：

  A short and practical route to the tricyclic core of an unnatural pseudopterosin diastereoisomer is presented. Key features are an arene alkylation with a gamma -methylene-gamma -butyrolactone, viz. 10 --> 14, and an elaborate reduction sequence 14 --> 17 which both proceed diastereoselectively. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)02207-3

文献信息

• Radical induced fragmentation in a benzoxocane ring system: application to the synthesis of elvirol and a formal synthesis of 7,8-dihydroxycalamenene
  作者：Amalesh Roy、Kazi Tuhina、Bidyut Biswas、Ramanathapuram V. Venkateswaran

  DOI：10.1016/j.tet.2012.05.041

  日期：2012.8

  A novel radical induced fragmentation in a benzoxocane ring system has been employed for a synthesis of elvirol 8 and an advanced intermediate in the synthesis of 7,8-dihydroxycalamenene 20. The coumarins 9, 22 were taken through a sequence of reactions to the benzoxocanols 16, 30, which when subjected to Barton’s deoxygenation conditions involving conversion to the corresponding thionocarbonates 17

  苯并恶烷环系统中的新型自由基诱导的断裂已被用于合成elvirol 8和合成7,8-dihydroxycalamenene 20中的高级中间体。香豆素9，22通过一系列反应被带到benzoxocanols 16，30，其在经受巴顿的涉及转化为相应的thionocarbonates脱氧条件17，31，随后通过暴露于三- Ñ -butyltin氢化物，进行了自由基诱导裂解得到elvirol 8和姜酚衍生物32，其被转化为二甲氧基化合物33。在先前的二羟基cal草烯的合成中，它已被用作高级中间体。
• Structure revision of HM-3, an aromatic sesquiterpene isolated from the phytopathogenic fungus Helicobasidium mompa. First total syntheses of HM-3 and HM-4
  作者：A. Srikrishna、P.C. Ravikumar

  DOI：10.1016/j.tet.2006.07.062

  日期：2006.10

  The first total syntheses of HM-3 and HM-4 aromatic sesquiterpenes isolated from the phytopathogenic fungus Helicobasidium mompa, have been accomplished. The structure assigned to the sesquiterpene HM-3 was found to be incorrect by total synthesis. A Claisen rearrangement-RCM reaction based strategy was employed for the total synthesis of the aromatic sesquiterpene HM-4 (cuparene-1,2-diol), which on selective monoacetylation established the structure of HM-3, a cuparene derivative. (c) 2006 Elsevier Ltd. All rights reserved.
• MILLS F. D., J. HETEROCYCL. CHEM., 1980, 17, NO 7, 1597-1600
  作者：MILLS F. D.

  DOI：——

  日期：——
• Mills, Frank D., Journal of Heterocyclic Chemistry, 1980, vol. 17, p. 1597 - 1600
  作者：Mills, Frank D.

  DOI：——

  日期：——
• A new approach to the pseudopterosins using an arene alkylation with a γ-methylene-γ-butyrolactone
  作者：David C Harrowven、Jonathan D Wilden、Melloney J Tyte、Michael B Hursthouse、Simon J Coles

  DOI：10.1016/s0040-4039(00)02207-3

  日期：2001.2

  A short and practical route to the tricyclic core of an unnatural pseudopterosin diastereoisomer is presented. Key features are an arene alkylation with a gamma -methylene-gamma -butyrolactone, viz. 10 --> 14, and an elaborate reduction sequence 14 --> 17 which both proceed diastereoselectively. (C) 2001 Elsevier Science Ltd. All rights reserved.