5,7-dichloro-3-ethoxycarbonylbenzofuran | 899795-66-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 5,7-dichloro-3-ethoxycarbonylbenzofuran
• 英文别名: ethyl 5,7-dichlorobenzofuran-3-carboxylate；ethyl 5,7-dichloro-1-benzofuran-3-carboxylate
• CAS: 899795-66-5
• 化学式: C₁₁H₈Cl₂O₃
• 分子量: 259.089
• InChiKey: BFQQJMGERPUFTI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  5,7-dichloro-3-ethoxycarbonylbenzofuran 在 一水合肼 作用下， 以 乙醇 为溶剂， 生成 5,7-dichlorobenzofuran-3-carbohydrazide
  参考文献：
  名称：

  Novel N′-benzylidene benzofuran-3-carbohydrazide derivatives as antitubercular and antifungal agents

  摘要：

  Tuberculosis constitutes today a serious threat to human health worldwide, aggravated by the increasing number of identified multi-drug resistant strains of Mycobacterium tuberculosis (Mtb), its causative agent, as well as by the lack of development of novel mycobactericidal compounds for the last few decades. A novel series of benzofuran-3-carbohydrazide and its analogs was synthesized and characterized spectroscopically. All the compounds were characterized and screened for in vitro anti-tuberculosis (anti-TB) activity against Mycobacterium tuberculosis H37Rv strains by using resazurin assay utilizing microtiter-plate method (REMA). These compounds also showed good antifungal activity against Candida albicans. Thus, the high level of activity shown by the compounds (8a, 8k) suggests that these compounds could serve as leads for development of novel synthetic compounds with enhanced anti- TB and antifungal activity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.01.067
• 作为产物：
  描述：

  (E)-3-(2,4-dichlorophenoxy)acrylic acid ethyl ester 在 palladium diacetate 、 silver trifluoroacetate 、 三苯基膦 作用下， 以 苯 为溶剂， 反应 24.0h， 以51%的产率得到5,7-dichloro-3-ethoxycarbonylbenzofuran
  参考文献：
  名称：

  钯催化3-苯氧基丙烯酸酯的氧化环化：一种由苯酚取代苯并呋喃的方法

  摘要：

  在本文中，已经开发了一种新颖且适用的由市售苯酚和丙酸酯通过直接氧化环化反应合成苯并呋喃的方法。在Pd（OAc）2 / PPh 3和CF 3 CO 2 Ag的存在下，（E）型3-苯氧基丙烯酸酯在空气中于110°C的条件下顺利进行反应，以高收率在苯中生成相应的苯并呋喃。此外，苯酚向苯并呋喃的这种转化也可以在一锅中进行。该过程既简单又高效。提出了3-苯氧基丙烯酸酯钯催化氧化环化的初步机理。

  DOI：

  10.1021/jo200317f

文献信息

• A Convenient Method of Synthesizing 3-Ethoxycarbonylbenzofurans from Salicylaldehydes and Ethyl Diazoacetate
  作者：M. Hossain、Matthew Dudley、M. Morshed

  DOI：10.1055/s-2006-926454

  日期：2006.5

  We have developed a convenient one-pot procedure for the synthesis of 3-ethoxycarbonylbenzofurans from commercially available salicylaldehydes and ethyl diazoacetate. The method is high-yielding, efficient, simple and selective.

  我们开发了一种方便的一锅法，用于从市售的水杨醛和重氮乙酸乙酯合成 3-乙氧基羰基苯并呋喃。该方法高产、高效、简便、选择性好。
• Convenient Preparation of 3-Ethoxycarbonyl Benzofurans from Salicylaldehydes and Ethyl Diazoacetate
  作者：Matthew E. Dudley、M. Monzur Morshed、M. Mahmun Hossain.

  DOI：10.1002/0471264229.os086.18

  日期：2009.12.18
• Novel N′-benzylidene benzofuran-3-carbohydrazide derivatives as antitubercular and antifungal agents
  作者：Vikas N. Telvekar、Anirudh Belubbi、Vinod Kumar Bairwa、Kalpana Satardekar

  DOI：10.1016/j.bmcl.2012.01.067

  日期：2012.3

  Tuberculosis constitutes today a serious threat to human health worldwide, aggravated by the increasing number of identified multi-drug resistant strains of Mycobacterium tuberculosis (Mtb), its causative agent, as well as by the lack of development of novel mycobactericidal compounds for the last few decades. A novel series of benzofuran-3-carbohydrazide and its analogs was synthesized and characterized spectroscopically. All the compounds were characterized and screened for in vitro anti-tuberculosis (anti-TB) activity against Mycobacterium tuberculosis H37Rv strains by using resazurin assay utilizing microtiter-plate method (REMA). These compounds also showed good antifungal activity against Candida albicans. Thus, the high level of activity shown by the compounds (8a, 8k) suggests that these compounds could serve as leads for development of novel synthetic compounds with enhanced anti- TB and antifungal activity. (C) 2012 Elsevier Ltd. All rights reserved.
• Palladium-Catalyzed Oxidative Cyclization of 3-Phenoxyacrylates: An Approach To Construct Substituted Benzofurans from Phenols
  作者：Chengliang Li、Yicheng Zhang、Pinhua Li、Lei Wang

  DOI：10.1021/jo200317f

  日期：2011.6.3

  applicable synthesis of benzofurans from commercially available phenols and propiolate through the direct oxidative cyclization has been developed. In the presence of Pd(OAc)2/PPh3 and CF3CO2Ag, (E)-type 3-phenoxyacrylates underwent reaction smoothly to generate the corresponding benzofurans in good yields in benzene at 110 °C under the air pressure. In addition, this transformation of phenols into benzofurans

  在本文中，已经开发了一种新颖且适用的由市售苯酚和丙酸酯通过直接氧化环化反应合成苯并呋喃的方法。在Pd（OAc）2 / PPh 3和CF 3 CO 2 Ag的存在下，（E）型3-苯氧基丙烯酸酯在空气中于110°C的条件下顺利进行反应，以高收率在苯中生成相应的苯并呋喃。此外，苯酚向苯并呋喃的这种转化也可以在一锅中进行。该过程既简单又高效。提出了3-苯氧基丙烯酸酯钯催化氧化环化的初步机理。