methyl 2-(2-chlorophenyl)furan-3-carboxylate | 1459238-19-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: methyl 2-(2-chlorophenyl)furan-3-carboxylate
• 英文别名: Methyl 2-(2-chlorophenyl)furan-3-carboxylate
• CAS: 1459238-19-7
• 化学式: C₁₂H₉ClO₃
• 分子量: 236.655
• InChiKey: WRHQOBQGIVGNAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 2-(2-chlorophenyl)furan-3-carboxylate 在 噻吩-2-甲酸亚铜(I) 、 四甲基乙二胺 、 caesium carbonate 作用下， 以 水 为溶剂， 300.0 ℃ 、1.72 MPa 条件下， 反应 0.17h， 以30%的产率得到4H-furo[3,2-c]chromen-4-one
  参考文献：
  名称：

  Cu(I)-mediated lactone formation in subcritical water: a benign synthesis of benzopyranones and urolithins A–C

  摘要：

  Benzopyranones were successfully synthesized using Cu(I)-mediated C-O bond formation in subcritical water. A number of benzopyranone derivatives including polymethoxy benzopyranones, benzopyranopyridones, cbromenoindolones, and furochromenones were synthesized in satisfactory yield. This methodology was further applied to synthesize the intestinal microbial metabolites, urolithins A, B, and C, which were found to exhibit potent antioxidant activity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.08.045
• 作为产物：
  描述：

  2-氯苄氧基乙酸甲酯 、 二乙二醇 在 叔丁基过氧化氢 、 copper(II) bis(tetrafluoroborate) 作用下， 以 水 为溶剂， 反应 5.0h， 以45%的产率得到methyl 2-(2-chlorophenyl)furan-3-carboxylate
  参考文献：
  名称：

  Diethylene Glycol Serving as Ethyne Equivalent: A Sustainable Approach toward 2,3-Disubstituted Furan

  摘要：

  In the presence of tert-butyl peroxide (TBHP), the copper-catalyzed annulation of 1,3-dicarbonyl compound with diethylene glycol was developed leading to 2,3-disubstituted furan. Diethylene glycol serves as a cheap and environmentally friendly equivalent of ethyne, with the release of H2O and alcohol as clean wastes The procedure involves a sequential O- and C-functionalization of beta-ketoester by diethylene glycol.

  DOI：

  10.1021/acs.orglett.5b01521

文献信息

• Diethylene Glycol Serving as Ethyne Equivalent: A Sustainable Approach toward 2,3-Disubstituted Furan
  作者：Jin-Tao Yu、Bo Shi、Haibo Peng、Song Sun、Haoke Chu、Yan Jiang、Jiang Cheng

  DOI：10.1021/acs.orglett.5b01521

  日期：2015.8.7

  In the presence of tert-butyl peroxide (TBHP), the copper-catalyzed annulation of 1,3-dicarbonyl compound with diethylene glycol was developed leading to 2,3-disubstituted furan. Diethylene glycol serves as a cheap and environmentally friendly equivalent of ethyne, with the release of H2O and alcohol as clean wastes The procedure involves a sequential O- and C-functionalization of beta-ketoester by diethylene glycol.
• Cu(I)-mediated lactone formation in subcritical water: a benign synthesis of benzopyranones and urolithins A–C
  作者：Prattya Nealmongkol、Kassrin Tangdenpaisal、Somkid Sitthimonchai、Somsak Ruchirawat、Nopporn Thasana

  DOI：10.1016/j.tet.2013.08.045

  日期：2013.11

  Benzopyranones were successfully synthesized using Cu(I)-mediated C-O bond formation in subcritical water. A number of benzopyranone derivatives including polymethoxy benzopyranones, benzopyranopyridones, cbromenoindolones, and furochromenones were synthesized in satisfactory yield. This methodology was further applied to synthesize the intestinal microbial metabolites, urolithins A, B, and C, which were found to exhibit potent antioxidant activity. (C) 2013 Elsevier Ltd. All rights reserved.