5-chloro-2-furancarbohydroximoyl chloride

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 5-chloro-2-furancarbohydroximoyl chloride
• 英文别名: 5-Chloro-N-hydroxyfuran-2-carbonimidoyl chloride；(2Z)-5-chloro-N-hydroxyfuran-2-carboximidoyl chloride
• 化学式: C₅H₃Cl₂NO₂
• 分子量: 179.99
• InChiKey: UBFTXRZQCYKTLE-YVMONPNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  丙烯酸甲酯（MA） 、 5-chloro-2-furancarbohydroximoyl chloride 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以80%的产率得到methyl 3-(5-chloro-2-furyl)-2-isoxazoline-5-carboxylate
  参考文献：
  名称：

  Synthesis of Hydroximoyl Chlorides from Aldoximes and Benzyltrimethylammonium Tetrachloroiodate (BTMA ICl4)

  摘要：

  Benzyltrimethylammonium tetrachloroiodate (BTMA ICl4) acts as a convenient reagent to convert aldoximes to hydroximoyl chlorides by a simple procedure. When an aldoxime is treated with BTMA ICl4 in dichloromethane, the suspension of BTMA ICl4 shortly diasappears as the reaction proceeds. The resulting BTMA ICl2 can he precipitated out by adding diethyl ether. Not only stable aromatic and heteroaromatic hydroximoyl chlorides can be isolated by this method but also rather unstable aliphatic hydroximoyl chlorides can be generated in situ. 1,3-Dipole trapping with a dipolarophile is performed in one flask and in some cases the chlorination is successfully performed in the presence of dipolarophile and triethylamine. Effect of MS 4A has been examined. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)01047-9
• 作为产物：
  描述：

  (E)-1-(2-呋喃基)-N-羟基甲亚胺 在 N-氯代丁二酰亚胺 、 benzyltrimethylazanium tetrachloro-λ³-iodanuide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.08h， 生成 5-chloro-2-furancarbohydroximoyl chloride
  参考文献：
  名称：

  Synthesis of Hydroximoyl Chlorides from Aldoximes and Benzyltrimethylammonium Tetrachloroiodate (BTMA ICl4)

  摘要：

  Benzyltrimethylammonium tetrachloroiodate (BTMA ICl4) acts as a convenient reagent to convert aldoximes to hydroximoyl chlorides by a simple procedure. When an aldoxime is treated with BTMA ICl4 in dichloromethane, the suspension of BTMA ICl4 shortly diasappears as the reaction proceeds. The resulting BTMA ICl2 can he precipitated out by adding diethyl ether. Not only stable aromatic and heteroaromatic hydroximoyl chlorides can be isolated by this method but also rather unstable aliphatic hydroximoyl chlorides can be generated in situ. 1,3-Dipole trapping with a dipolarophile is performed in one flask and in some cases the chlorination is successfully performed in the presence of dipolarophile and triethylamine. Effect of MS 4A has been examined. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)01047-9

文献信息

• A fast route for the synthesis of tetrazolyl oximes by a novel multicomponent reaction between Z-chlorooximes, isocyanides and trimethylsilyl azide
  作者：Mariateresa Giustiniano、Sveva Pelliccia、Ana Belen Muñoz-Garcia、Michele Pavone、Bruno Pagano、Ubaldina Galli、Ettore Novellino、Gian Cesare Tron

  DOI：10.1016/j.tetlet.2017.07.098

  日期：2017.9

  prepared in one single synthetic step exploiting the combination of (Z)-chlorooximes, isocyanides and trimethylsilyl azide. The formal [3+1] cycloaddition between isocyanides and nitrile N-oxides with respect to the [3+1] cycloaddition between isocyanides and azides prevails, while the direct attack of azide onto nitrile N-oxides remains competitive. Finally, an intramolecular cyclization of a (1H-tetrazol-5-yl)methanone

  利用（Z）-氯肟，异氰化物和三甲基硅烷基叠氮化物的组合，在一个单一的合成步骤中制备了二十种装饰不同的1,5-二取代-（1 H-四唑-5-基）甲酮肟的文库。相对于异氰酸酯和叠氮化物之间的[3 + 1]环加成，异氰酸酯和腈N-氧化物之间的正式的[3 + 1]环加成占主导，而叠氮化物对腈N-氧化物的直接攻击仍然具有竞争力。最后，首次报道了（1 H-四唑-5-基）甲酮肟的分子内环化为苯并异恶唑四唑。
• AMINOISOXAZOLE DERIVATIVES ACTIVE AS KINASE INHIBITORS
  申请人：Pharmacia Italia S.p.A.

  公开号：EP1435948A1

  公开（公告）日：2004-07-14
• [EN] AMINOISOXAZOLE DERIVATIVES ACTIVE AS KINASE INHIBITORS<br/>[FR] DÉRIVÉS D'AMINOISOXAZOLE AGISSANT COMME INHIBITEURS DE LA KINASE
  申请人：PHARMACIA ITALIA SPA

  公开号：WO2003013517A1

  公开（公告）日：2003-02-20

  Compounds (I) which are aminoisoxazole derivatives or pharmaceutically acceptable salts thereof, together with pharmaceutical compositions comprising them are disclosed; these compounds or compositions are useful in the treatment of diseases caused by and/or associated with an altered protein kinase activity such as cancer, cell proliferative disorders, Alzheimer's disease, viral infections, auto-immune diseases and neurodegenerative disorders.
• Synthesis of Hydroximoyl Chlorides from Aldoximes and Benzyltrimethylammonium Tetrachloroiodate (BTMA ICl4)
  作者：Shuji Kanemasa、Haruhiko Matsuda、Akio Kamimura、Takaaki Kakinami

  DOI：10.1016/s0040-4020(99)01047-9

  日期：2000.2

  Benzyltrimethylammonium tetrachloroiodate (BTMA ICl4) acts as a convenient reagent to convert aldoximes to hydroximoyl chlorides by a simple procedure. When an aldoxime is treated with BTMA ICl4 in dichloromethane, the suspension of BTMA ICl4 shortly diasappears as the reaction proceeds. The resulting BTMA ICl2 can he precipitated out by adding diethyl ether. Not only stable aromatic and heteroaromatic hydroximoyl chlorides can be isolated by this method but also rather unstable aliphatic hydroximoyl chlorides can be generated in situ. 1,3-Dipole trapping with a dipolarophile is performed in one flask and in some cases the chlorination is successfully performed in the presence of dipolarophile and triethylamine. Effect of MS 4A has been examined. (C) 2000 Elsevier Science Ltd. All rights reserved.