ethyl 6-chloro-2-hydroxy-2-(trifluoromethyl)-2H-chromene-3-carboxylate | 1353720-23-6

• 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: ethyl 6-chloro-2-hydroxy-2-(trifluoromethyl)-2H-chromene-3-carboxylate
• 英文别名: Ethyl 6-chloro-2-hydroxy-2-(trifluoromethyl)chromene-3-carboxylate；ethyl 6-chloro-2-hydroxy-2-(trifluoromethyl)chromene-3-carboxylate
• CAS: 1353720-23-6
• 化学式: C₁₃H₁₀ClF₃O₄
• 分子量: 322.668
• InChiKey: YWQQLTJTGZUWHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 6-chloro-2-hydroxy-2-(trifluoromethyl)-2H-chromene-3-carboxylate 以 neat (no solvent) 为溶剂， 反应 0.05h， 生成
  参考文献：
  名称：

  Microwave-assisted TsOH/SiO 2 -catalyzed one-pot synthesis of novel fluoro-substituted coumarin hydrazones under solvent-free conditions

  摘要：

  Sixteen novel fiuoro-substituted coumarin hydrazones were synthesized from a series of ethyl 2-hydroxy-2-(trifluoromethyl)-2H-chromene-3-carboxylates with supported acid catalyst under microwave-assisted one-pot and solvent free conditions. The structures of synthesized compounds were confirmed by IR, H-1 NMR, C-13 NMR, HRMS and single crystal X-ray diffraction. Compared with the reported reaction conditions, the new method has the advantages of shorter reaction time, simple workup procedure and environmental friendliness. The supported catalyst can be recovered easily and reused with little change in its activity. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2014.07.004
• 作为产物：
  描述：

  三氟乙酰乙酸乙酯 、 5-氯代水杨醛 在 L-proline/SiO₂ 作用下， 反应 0.23h， 以81%的产率得到ethyl 6-chloro-2-hydroxy-2-(trifluoromethyl)-2H-chromene-3-carboxylate
  参考文献：
  名称：

  An Efficient Solvent-Free Synthesis of 2-Hydroxy-2-(trifluoromethyl)-2H-chromenes Using Silica-Immobilized L-Proline

  摘要：

  在无溶剂条件下，通过在烤箱或微波炉中将水杨 aldehydes 与三氟乙酰乙酸乙酯进行 Knoevenagel 缔合反应，然后在硅胶固定的 L-脯氨酸存在下进行分子内环化，成功合成了 2-羟基-2-(三氟甲基)-2H-香豆烯-3-羧酸酯。标题化合物的结构通过 IR、1H-NMR、13C-NMR、HRMS 和 X 射线单晶衍射进行表征。此处描述的改进方法经济、操作简便且环保。此外，催化剂可以方便地回收和重复使用，且活性无明显损失。

  DOI：

  10.3390/molecules181011964

文献信息

• Reactions of 2-(trifluoromethyl)-2-hydroxy-2H-chromenes with silyl enol ethers promoted by AlCl3
  作者：Liang Zhang、Xinjin Li、Zhongwei Wang、Jingwei Zhao、Jinjin Wang、Jianwei Han、Shizheng Zhu

  DOI：10.1016/j.tet.2013.07.004

  日期：2013.9

  An efficient and straightforward nucleophilic substitution reaction between 2-(trifluoromethyl)-2-hydroxy-2H-chromenes and various silyl enol ethers promoted by Lewis acid has been studied. A series of novel 4-functionalized-2-trifluoromethyl-3-ethoxycarbonyl-4H-chromenes were prepared in good yields under mild conditions.

  2-（三氟甲基）之间的有效的和直接的亲核取代反应-2-羟基-2- ħ -chromenes和由路易斯酸促进的各种甲硅烷基烯醇醚进行了研究。在温和的条件下以高收率制备了一系列新颖的4-官能化的-2-三氟甲基-3-乙氧基羰基-4 H-色烯。
• Regioselective Carbon-Carbon Bond Formation in the Reaction of 2-Hydroxy-2-(trifluoromethyl)-2H-chromenes with Indoles Promoted by Lewis Acid
  作者：Shi Zhu、Wan Pang、Jian Han、Jing Zhao

  DOI：10.1055/s-0030-1260202

  日期：2011.10

  efficient Lewis acid mediated C-C coupling reaction between readily available 2-hydroxy-2-(trifluoro­methyl)-2H-chromenes and various indoles via regioselective nucleophilic substitution has been developed. On the basis of this methodology, a series of bio- and pharmacologically important 2- and 4-functionalized 2-(trifluoromethyl)-2H-chromenes were prepared in high yields. regioselective - C-C bond formation

  已经开发了一种简单有效的路易斯酸介导的通过区域选择性亲核取代的2-羟基-2-（三氟甲基）-2 H-色烯与各种吲哚之间的CC偶联反应。基于该方法，以高收率制备了一系列生物和药理学上重要的2-和4-官能化的2-（三氟甲基）-2 H-色烯。 区域选择性-CC键形成-2 H-色烯-吲哚-路易斯酸
• Reactions of 2-(trifluoromethyl)-2-hydroxy-2H-chromenes with thiophenols promoted by Lewis acid
  作者：Xinjin Li、Jingwei Zhao、Zhongwei Wang、Jianwei Han、Jian Zhao、Shizheng Zhu

  DOI：10.1016/j.tet.2012.06.101

  日期：2012.9

  A Lewis acid promoted nucleophilic substitution reaction between 2-(trifluoromethyl)-2-hydroxy-3-ethoxycarbonyl-2H-chromenes 1 and thiophenols affording thiophenyl substituted products, that is, 4-thiophenyl-2-trifluoromethyl-3-ethoxycarbonyl-4H-chromene and 2-thiophenyl-2-trifluoromethyl-3-ethoxycarbonyl-2H-chromene.

  路易斯酸促进2-（三氟甲基）-2-羟基-3-乙氧基羰基-2 H-色酮1与提供苯硫基取代产物的苯酚，即4-硫苯基-2-三氟甲基-3-乙氧基羰基-4之间的亲核取代反应。H-色烯和2-硫代苯基-2-三氟甲基-3-乙氧基羰基-2 H-色烯。
• Vishnu; Srikanth; Tiwari, Ashok K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2015, vol. 54B, # 11, p. 1332 - 1341
  作者：Vishnu、Srikanth、Tiwari, Ashok K.、Kumar, D. Anand、Raju, B. China

  DOI：——

  日期：——
• An Efficient Solvent-Free Synthesis of 2-Hydroxy-2-(trifluoromethyl)-2H-chromenes Using Silica-Immobilized L-Proline
  作者：Cuilian Xu、Guoyu Yang、Caixia Wang、Sufang Fan、Lixia Xie、Ya Gao

  DOI：10.3390/molecules181011964

  日期：——

  An efficient synthesis of 2-hydroxy-2-(trifluoromethyl)-2H-chromene-3-carboxylates was carried out under solvent-free conditions in an oven or microwave oven via the Knoevenagel condensation of salicylaldehydes with ethyl trifluoroacetoacetate followed by intramolecular cyclization in the presence of silica-immobilized L-proline. The structures of the title compounds were characterized by IR, 1H-NMR, 13C-NMR, HRMS and X-ray single crystal diffraction. The improved method described herein is economical, easily-operated and environmentally friendly. Furthermore, the catalyst can be recovered conveniently and reused without obvious loss of activity.

  在无溶剂条件下，通过在烤箱或微波炉中将水杨 aldehydes 与三氟乙酰乙酸乙酯进行 Knoevenagel 缔合反应，然后在硅胶固定的 L-脯氨酸存在下进行分子内环化，成功合成了 2-羟基-2-(三氟甲基)-2H-香豆烯-3-羧酸酯。标题化合物的结构通过 IR、1H-NMR、13C-NMR、HRMS 和 X 射线单晶衍射进行表征。此处描述的改进方法经济、操作简便且环保。此外，催化剂可以方便地回收和重复使用，且活性无明显损失。