2,3-dimethyl-5H-benzo(c)chromene-5-one | 127599-32-0

• 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: 2,3-dimethyl-5H-benzo(c)chromene-5-one
• 英文别名: 8,9-dimethyl-6H-benzo[c]chromen-6-one；8,9-dimethyl-benzo[c]chromen-6-one；8,9-Dimethyl-benzo[c]chromen-6-on；8,9-Dimethylbenzo[c]chromen-6-one
• CAS: 127599-32-0
• 化学式: C₁₅H₁₂O₂
• 分子量: 224.259
• InChiKey: FGMMWKHQMPDRHY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  反式-2-羟基肉桂酸 在 palladium on activated charcoal 、 二氧化碳 、 xylene 作用下， 生成 2,3-dimethyl-5H-benzo(c)chromene-5-one
  参考文献：
  名称：

  The Addition of Dienes to Coumarin and to Certain Substituted Cinnamic Acids. I.

  摘要：

  DOI：

  10.1021/ja01243a017

文献信息

• A metal-free one-pot synthesis of benzo[c]chromen-6-ones from 3,4-dichlorocoumarins and butadienes using tandem photo-thermal-photo reactions
  作者：Yan Zhang、Yan Tian、Pei Xiang、Ning Huang、Jianyi Wang、Jian-Hua Xu、Min Zhang

  DOI：10.1039/c6ob01701k

  日期：——

  of biologically valuable benzo[c]chromen-6-ones is achieved using a tandem photo-thermal-photo reaction sequence starting from 3,4-dichlorocoumarins and a 1,3-butadiene. In this concise one-pot protocol, neither metal catalyst nor peroxide promoter is needed and the products can be purified through simple recrystallization in most cases. The synthesis consists of a reaction sequence of photo-induced

  使用从3,4-二氯香豆素和1,3-丁二烯开始的串联光热反应过程，可以有效，简单，通用地合成具有生物学价值的苯并[ c ] chromen-6-one。在这种简洁的一锅法方案中，不需要金属催化剂或过氧化物促进剂，并且在大多数情况下，可以通过简单的重结晶来纯化产物。合成过程包括光诱导的[4 + 2]和[2 + 2]环加成反应的顺序，硅胶促进的HCl消除和电环环丁烯开环，然后进行光诱导的6π电环化。用一系列二氯香豆素和一些典型的丁二烯可以很好地进行反应，从而以70-80％的产率提供相应的环状产物。
• Synthesis of Fluorenone and Anthraquinone Derivatives from Aryl- and Aroyl-Substituted Propiolates
  作者：Florian Pünner、Justin Schieven、Gerhard Hilt

  DOI：10.1021/ol4023276

  日期：2013.9.20

  Fluorenone derivatives were generated from aryl-substituted propiolates via a cobalt-catalyzed Diels-Alder reaction/DDQ-oxidation and Friedel-Crafts-type cyclization. Several functional groups are tolerated, and good to excellent overall yields (up to 89%) could be achieved. For the synthesis of anthraquinone derivatives, aroyl-substituted propiolates were applied in a zinc iodide catalyzed Die Is Alder reaction with 1,3-dienes. The subsequent DDQ oxidation and Friedel-Crafts-type cyclization led to symmetrical as well as some unsymmetrical anthraquinones in good to excellent yields of up to 87% over the three-step reaction sequence.
• 4-Phenylsulphinyl- and 4-phenylsulphonylcoumarins as 2π - components in cycloaddition reactions.
  作者：Ronald Grigg、D. Vipond

  DOI：10.1016/s0040-4020(01)89220-6

  日期：1989.1
• The Addition of Dienes to Coumarin and to Certain Substituted Cinnamic Acids. I.
  作者：Roger Adams、W. D. McPhee、R. B. Carlin、Z. W. Wicks

  DOI：10.1021/ja01243a017

  日期：1943.3