2-azidobenzohydroximoyl chloride | 141246-98-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-azidobenzohydroximoyl chloride
• 英文别名: 2-Azido-N-hydroxybenzene-1-carboximidoyl chloride；2-azido-N-hydroxybenzenecarboximidoyl chloride
• CAS: 141246-98-2
• 化学式: C₇H₅ClN₄O
• 分子量: 196.596
• InChiKey: OMVDWOHEBRPNCK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  47
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-azidobenzohydroximoyl chloride 在 三乙胺 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 52.0h， 生成 3-(2-azidophenyl)-5-ethylthio-1,2,4-oxadiazole
  参考文献：
  名称：

  1,2,4-Oxadiazoles from cycloreversions of oxadiazabicyclo[3.2.0]heptenes: 1-azetines as thiocyanate equivalents

  摘要：

  1,3-Dipolar cycloaddition of nitrile oxides to 4-aryl-2-alkylthio-1-azetines gave a series of oxadiazabicyclo[3.2.0]heptenes as single diastereoisomers. Heating these cycloadducts in toluene resulted in an overall [2+2]-cycloreversion to give 5-alkylthio-3-aryl-1,2,4-oxadiazoles. In this process, the 1-azetine behaves as a thiocyanate equivalent. When the nitrile oxide substituent was 2-azidobenzene, the azide could be converted into a 1,2,3-triazole giving a (1,2,4-oxadiazolo)-(1,2,3-triazolo)-1,2-disubstituted benzene. 1,2,4-Oxadiazoles are sought after in medicinal chemistry and materials sciences. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.12.007

文献信息

• Tetrazolo[1,5-a]quinolines and 1,2,3-Triazolo[1,5-a]quinazolines by the Action of Cyanocarbanions on 2-azidoarylcarbonyl Compounds
  作者：Thomas C. Porter、Robert K. Smalley、Mabrouk Teguiche、Bambang Purwono

  DOI：10.1055/s-1997-1416

  日期：1997.7

  In protic solvents, 2-azidobenzaldehyde undergoes base-catalysed condensation with cyanocarbanions to yield tetrazolo[1,5-a]quinolines 5a-g, whereas in aprotic media 1,2,3-triazolo[1,5-a]quinazolines 6a-f are formed. Triazoloquinazolines 9a-g are also obtained from 2'-azidoacetophenone and from 2-azidobenzonitrile, whereas with 2-azidobenzoyl chloride hydroxytetrazoloquinolines 13a,b result. 2,1-Oxazolo[4,3-c]tetrazolo[1,5-a]quinolines 20a,b are obtained by the action of selected cyanocarbanions on 2-azidobenzonitrile oxide 15 and a 1,2,3-triazolo[1,5-a]quinoline 22 by base-catalysed condensation of 2-azidobenzonitrile with 1,3-diphenylpropan-2-one.

  在质子溶剂中，2-叠氮苯甲醛与氰基碳阴离子在碱催化下发生缩合反应，生成四唑[1,5-a]喹啉5a-g，而在非质子介质中则形成1,2,3-三唑[1,5-a]喹唑啉6a-f。三唑喹唑啉9a-g也可以通过2'-叠氮苯乙酮和2-叠氮苯腈得到，而与2-叠氮苯甲酰氯反应则产生氢氧四唑喹啉13a,b。2,1-噁唑[4,3-c]四唑[1,5-a]喹啉20a,b是通过特定的氰基碳阴离子与2-叠氮苯腈氧化物15反应获得的，而1,2,3-三唑[1,5-a]喹啉22则是通过2-叠氮苯腈与1,3-二苯基丙酮的碱催化缩合反应生成的。
• Synthesis, conformation and antiproliferative activity of isothiazoloisoxazole 1,1-dioxides
  作者：J. Blackburn、G. Molyneux、A. Pitard、C. R. Rice、M. I. Page、S. Afshinjavid、F. A. Javid、S. J. Coles、P. N. Horton、K. Hemming

  DOI：10.1039/c5ob02586a

  日期：——

  Sixteen new isothiazoloisoxazole 1,1-dioxides, one new isothiazolotriazole and one new isothiazolopyrazole have been synthesised by using 1,3-dipolar cycloadditions to isothiazole 1,1-dioxides. One sub-set of these isothiazoloisoxazoles showed low μM activity against a human breast carcinoma cell line, whilst a second sub-set plus the isothiazolotriazole demonstrated an interesting restricted rotation

  通过使用1，3-偶极环加成到异噻唑1，1-二氧化物上，已合成了十六种新的异噻唑并异恶唑1，1-二氧化物，一种新的异噻唑并三唑和一种新的异噻唑并吡唑。这些异噻唑并异恶唑中的一个亚组显示出对人乳腺癌细胞系的低μM活性，而第二个亚组加上异噻唑并三唑则显示出空间受阻的桥头取代基有趣的受限旋转。用路易斯酸处理后，由异噻唑1，1-二氧化物之一生成的噻嗪1，1-二氧化物转化为未知的1,2,3-氧杂噻唑啉-2-氧化物，但对1,3-偶极和二甲苯是惰性的。环丙烯酮。包括六个支撑晶体结构。
• Pyridines from Azabicyclo[3.2.0]hept-2-en-4-ones through a Proposed Azacyclopentadienone
  作者：Karl Hemming、Musharraf N. Khan、Vishnu V. R. Kondakal、Arnaud Pitard、M. Ilyas Qamar、Craig R. Rice

  DOI：10.1021/ol202924s

  日期：2012.1.6

  Pyridines have been formed by heating azabicyclo[3.2.0]hept-2-en-4-ones in toluene. The generation of a 3-azacyclopentadienone intermediate via a [2 + 2]-cycloreversion Is proposed as the key step. A Diels-Alder reaction of a styrene, extrusion of carbon monoxide, and loss of hydrogen then gives the pyridine. The process parallels the well-known synthesis of benzenes from cyclopentadienones. The azabicyclo[3.2.0]hept-2-en-4-ones were synthesized from the reaction between readily available cyclopropenones and 1-azetines, In which the cyclopropenones behave as all-carbon 1,3-dipolar equivalents.
• 1,2,4-Oxadiazoles from cycloreversions of oxadiazabicyclo[3.2.0]heptenes: 1-azetines as thiocyanate equivalents
  作者：Karl Hemming、Musharraf N. Khan、Paul A. O'Gorman、Arnaud Pitard

  DOI：10.1016/j.tet.2012.12.007

  日期：2013.1

  1,3-Dipolar cycloaddition of nitrile oxides to 4-aryl-2-alkylthio-1-azetines gave a series of oxadiazabicyclo[3.2.0]heptenes as single diastereoisomers. Heating these cycloadducts in toluene resulted in an overall [2+2]-cycloreversion to give 5-alkylthio-3-aryl-1,2,4-oxadiazoles. In this process, the 1-azetine behaves as a thiocyanate equivalent. When the nitrile oxide substituent was 2-azidobenzene, the azide could be converted into a 1,2,3-triazole giving a (1,2,4-oxadiazolo)-(1,2,3-triazolo)-1,2-disubstituted benzene. 1,2,4-Oxadiazoles are sought after in medicinal chemistry and materials sciences. (c) 2012 Elsevier Ltd. All rights reserved.