2-(1-methoxy-9H-xanthen-9-yl)-1-phenylethanone | 1371535-35-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2-(1-methoxy-9H-xanthen-9-yl)-1-phenylethanone
• CAS: 1371535-35-1
• 化学式: C₂₂H₁₈O₃
• 分子量: 330.383
• InChiKey: GMBJZRNTYVSKQO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-羟基查耳酮 、 三氟甲烷磺酸3-甲氧基-2-(三甲基硅基)苯酯 在 caesium carbonate 、 cesium fluoride 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以57%的产率得到2-(1-methoxy-9H-xanthen-9-yl)-1-phenylethanone
  参考文献：
  名称：

  Synthesis of 9-substituted xanthenes by the condensation of arynes with ortho-hydroxychalcones

  摘要：

  The reaction of o-(trimethylsilyl)aryl triflates, CsF, and o-hydroxychalcones affords a general and efficient way to prepare biologically interesting 9-substituted xanthenes. This chemistry presumably proceeds by the tandem intermolecular nucleophilic attack of the phenoxide of the chalcone on the aryne and subsequent intramolecular Michael addition. The introduction of an external base, Cs2CO3, has proven beneficial in this reaction. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.02.072

文献信息

• Synthesis of 9-substituted xanthenes by the condensation of arynes with ortho-hydroxychalcones
  作者：Chun Lu、Anton V. Dubrovskiy、Richard C. Larock

  DOI：10.1016/j.tetlet.2012.02.072

  日期：2012.4

  The reaction of o-(trimethylsilyl)aryl triflates, CsF, and o-hydroxychalcones affords a general and efficient way to prepare biologically interesting 9-substituted xanthenes. This chemistry presumably proceeds by the tandem intermolecular nucleophilic attack of the phenoxide of the chalcone on the aryne and subsequent intramolecular Michael addition. The introduction of an external base, Cs2CO3, has proven beneficial in this reaction. (c) 2012 Elsevier Ltd. All rights reserved.