3-苯并呋喃乙酰氯 | 857283-98-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 中文名称: 3-苯并呋喃乙酰氯
• 中文别名: 苯并[B]呋喃-3-乙酰氯
• 英文名称: 2-(benzofuran-3-yl)acetyl chloride
• 英文别名: Benzo[b]furan-3-ylacetyl chloride；2-(1-benzofuran-3-yl)acetyl chloride
• CAS: 857283-98-8
• 化学式: C₁₀H₇ClO₂
• mdl: MFCD08271903
• 分子量: 194.617
• InChiKey: HDUZJCZRUHHTNW-UHFFFAOYSA-N

物化性质

• 沸点：
  289.6±23.0 °C(Predicted)
• 密度：
  1.317±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险品标志：
  C
• 危险类别码：
  R14
• 危险品运输编号：
  UN 3265
• 海关编码：
  2932999099
• 安全说明：
  S23,S29,S30,S36/37/39,S45,S8

反应信息

• 作为反应物：
  描述：

  3-苯并呋喃乙酰氯 在 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 丙酮 为溶剂， 生成 3-(benzofuran-3-yl)-2-oxopropyl acetate
  参考文献：
  名称：

  2-(4-Chlorobenzyl)-3-hydroxy-7,8,9,10-tetrahydrobenzo[H]quinoline-4-carboxylic Acid (PSI-697):  Identification of a Clinical Candidate from the Quinoline Salicylic Acid Series of P-Selectin Antagonists

  摘要：

  P-selectin-PSGL-1 interaction causes rolling of leukocytes on the endothelial cell surface, which subsequently leads to firm adherence and leukocyte transmigration through the vessel wall into the surrounding tissues. P-selectin is upregulated on the surface of both platelets and endothelium in a variety of atherosclerosis-associated conditions. Consequently, inhibition of this interaction by means of a small molecule P-selectin antagonist is an attractive strategy for the treatment of atherosclerosis. High-throughput screening and subsequent analoging had led to the identification of compound 1 as the lead candidate. Herein, we report the continuation of this work and the discovery of a second-generation series, the tetrahydrobenzoquinoline salicylic acids. These compounds have improved pharmacokinetic properties, and a number of them have shown oral efficacy in mouse and rat models of atherogenesis and vascular injury. The lead 31 (PSI-697), is currently in clinical development for the treatment of atherothrombotic vascular events.

  DOI：

  10.1021/jm060631p
• 作为产物：
  描述：

  苯并呋喃-3-乙酸 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 生成 3-苯并呋喃乙酰氯
  参考文献：
  名称：

  通过室温Curtius重排轻松制备受保护的苄基和杂芳基甲基胺

  摘要：

  描述了用于形成酰基叠氮化物以及随后的苯基和杂芳基乙酸的Curtius重排的分步室温过程。我们已经开发出了在MeOH或CHCl 3中进行室温Curtius重排的规程，该规程比标准条件有所改进，避免了使用添加剂或加热。Curtius重排的这种室温优化可防止形成通常在苯甲酸中观察到的副产物，从而可以使用各种苯甲基和杂芳基甲基胺。

  DOI：

  10.1016/j.tetlet.2010.03.101

文献信息

• FUNCTIONALIZED HETEROCYCLES AS ANTIVIRAL AGENTS
  申请人：ENANTA PHARMACEUTICALS, INC

  公开号：US20200095258A1

  公开（公告）日：2020-03-26

  The present invention discloses compounds of Formula (I), or pharmaceutically acceptable salts, thereof: which inhibit the protein(s) encoded by hepatitis B virus (HBV) or interfere with the function of the HBV life cycle of the hepatitis B virus and are also useful as antiviral agents. The present invention further relates to pharmaceutical compositions comprising the aforementioned compounds for administration to a subject suffering from HBV infection. The invention also relates to methods of treating an HBV infection in a subject by administering a pharmaceutical composition comprising the compounds of the present invention.

  本发明公开了以下式（I）的化合物或其药学上可接受的盐：其抑制由乙型肝炎病毒（HBV）编码的蛋白质或干扰乙型肝炎病毒的生命周期功能，并且还可用作抗病毒剂。本发明还涉及包含上述化合物的药物组合物，用于治疗患有HBV感染的受试者。该发明还涉及通过给予包含本发明化合物的药物组合物来治疗受试者的HBV感染的方法。
• Cycloaddition Across the Benzofuran Ring as an Approach to the Morphine Alkaloids
  作者：Stefan France、Jutatip Boonsombat、Carolyn A. Leverett、Albert Padwa

  DOI：10.1021/jo8016956

  日期：2008.10.17

  The intramolecular Diels-Alder reaction of several amidofurans tethered onto a benzofuran ring was examined as a strategy for the synthesis of morphine. Bromo substitution on the furan ring did not provide sufficient activation to allow the cycloaddition to take place across the aromatic benzofuran. However, the presence of a large o-methylbenzyl group on the amido nitrogen atom causes the reactive s-trans conformation of the amidofuran to be highly populated, thereby facilitating its Diels-Alder cycloaddition across a tethered benzofuran.
• Intramolecular Carbenoid Insertions:  Reactions of α-Diazo Ketones Derived from Furanyl-, Thienyl-, (Benzofuranyl)-, and (Benzothienyl)acetic Acids with Rhodium(II) Acetate
  作者：Kelvin Yong、Mohamed Salim、Alfredo Capretta

  DOI：10.1021/jo9814593

  日期：1998.12.1

  alpha-Diazo ketones tethered to furan, benzofuran, thiophene, and benzothiophene by a single methylene spacer have been shown to undergo atypical, rhodium(II) acetate catalyzed chemistry. For example, while treatment of 1-diazo-3-(3-furanyl)-2-propanone with Rh-2(OAc)(4) resulted in the expected 2-(4-oxo-2-cyclopentenylidene)acetaldehyde, isomeric 1-diazo-3-(2-furanyl)-2-propanone undergoes a vinylogous Wolff rearrangement and in the presence of water gives a mixture of 6a-methyl-2,3,3a,6a-tetrahydrofuro[2,3-b]furan-2-one and 2-(2-methyl-3-furyl)acetic acid. Rhodium acetate catalyzed decomposition of 1-diazo-3-(3-benzofuranyl)-2-propanone and 1-diazo-3-(2-benzofuranyl)-2-propanone are also shown to undergo vinylogous Wolff rearrangement despite the fact that this chemistry is not observed with homologous benzofuranyl systems. alpha-Diazo ketones derived from benzothienyl propionic acids undergo the expected cyclization with 1-diazo-4-(3-benzothienyl)-2-butanone and 1-diazo-4-(2-benzothienyl)-2-butanone giving rise to 1,2,3,4-tetrahydrodibenzo[b,d]thiophen-3-one and 1,2,3,4-tetrahydrodibenzo[b,d]thiophen-2-one, respectively. While decomposition of 1-diazo-3-(3-benzothienyl)-2-propanone resulted in the formation of 2,3-dihydro-1H-benzo[b]cyclopenta[d]thiophen-a-one, the isomeric 1-diazo-3-(2-benzothienyl)-2-propanone gave a dimer which resulted from a [3 + 2] cycloaddition followed by a [1,3]-alkyl shift. Overall, the results from this study of intramolecular carbenoid insertion into five-membered heteroaromatic systems show that the resultant chemistry is dependent on the nature of the heteroatom, position of substitution, and the length of the aliphatic tether.
• 2-(4-Chlorobenzyl)-3-hydroxy-7,8,9,10-tetrahydrobenzo[<i>H</i>]quinoline-4-carboxylic Acid (PSI-697):  Identification of a Clinical Candidate from the Quinoline Salicylic Acid Series of P-Selectin Antagonists
  作者：Neelu Kaila、Kristin Janz、Adrian Huang、Alessandro Moretto、Silvano DeBernardo、Patricia W. Bedard、Steve Tam、Valerie Clerin、James C. Keith、Desirée H. H. Tsao、Natalia Sushkova、Gray D. Shaw、Raymond T. Camphausen、Robert G. Schaub、Qin Wang

  DOI：10.1021/jm060631p

  日期：2007.1.1

  P-selectin-PSGL-1 interaction causes rolling of leukocytes on the endothelial cell surface, which subsequently leads to firm adherence and leukocyte transmigration through the vessel wall into the surrounding tissues. P-selectin is upregulated on the surface of both platelets and endothelium in a variety of atherosclerosis-associated conditions. Consequently, inhibition of this interaction by means of a small molecule P-selectin antagonist is an attractive strategy for the treatment of atherosclerosis. High-throughput screening and subsequent analoging had led to the identification of compound 1 as the lead candidate. Herein, we report the continuation of this work and the discovery of a second-generation series, the tetrahydrobenzoquinoline salicylic acids. These compounds have improved pharmacokinetic properties, and a number of them have shown oral efficacy in mouse and rat models of atherogenesis and vascular injury. The lead 31 (PSI-697), is currently in clinical development for the treatment of atherothrombotic vascular events.
• Facile preparation of protected benzylic and heteroarylmethyl amines via room temperature Curtius rearrangement
  作者：Matthew L. Leathen、Emily A. Peterson

  DOI：10.1016/j.tetlet.2010.03.101

  日期：2010.5

  Curtius rearrangement of phenyl and heteroaryl acetic acids is described. We have developed a protocol for room temperature Curtius rearrangement in MeOH or CHCl3 that provides an improvement over standard conditions, avoiding the use of additives or heat. This room temperature optimization of the Curtius rearrangement prevents the formation of side products often observed with benzylic acids, allowing

  描述了用于形成酰基叠氮化物以及随后的苯基和杂芳基乙酸的Curtius重排的分步室温过程。我们已经开发出了在MeOH或CHCl 3中进行室温Curtius重排的规程，该规程比标准条件有所改进，避免了使用添加剂或加热。Curtius重排的这种室温优化可防止形成通常在苯甲酸中观察到的副产物，从而可以使用各种苯甲基和杂芳基甲基胺。