3-(4-Nitro-phenyl)-5-trichloromethyl-4,5-dihydro-isoxazol-5-ol | 187812-02-8

• 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: 3-(4-Nitro-phenyl)-5-trichloromethyl-4,5-dihydro-isoxazol-5-ol
• 英文别名: 5-Isoxazolol, 4,5-dihydro-3-(4-nitrophenyl)-5-(trichloromethyl)-；3-(4-nitrophenyl)-5-(trichloromethyl)-4H-1,2-oxazol-5-ol
• CAS: 187812-02-8
• 化学式: C₁₀H₇Cl₃N₂O₄
• 分子量: 325.536
• InChiKey: JPCVPJHVOZRREG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  87.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(4-Nitro-phenyl)-5-trichloromethyl-4,5-dihydro-isoxazol-5-ol 在 硫酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以92%的产率得到3-(4-Nitro-phenyl)-5-trichloromethyl-isoxazole
  参考文献：
  名称：

  卤代乙酰化的烯醇醚。7 †。3-芳基-5-三卤代甲基异恶唑和3-芳基-5-羟基-5-三卤代甲基-4,5-二氢异恶唑的合成

  摘要：

  β-芳基-β-甲氧基乙烯基三卤甲基酮1a-g，2a-g [芳基= p -YC 6 H 4，其中Y = H，Me，OMe，F，Cl，Br，NO 2 ]与羟胺盐酸盐环缩合得到3-芳基-5-羟基-5-三卤甲基-4，5-二氢异恶唑3a-g，4a-f具有良好的收率。用浓硫酸使化合物3a-g脱水，得到相应的3-芳基-5-三氯甲基异恶唑5a-g。另一种一锅法直接通过1,2a-g的环缩构反应生成3-芳基-5-三卤代甲基异恶唑5,6a -g 在过量浓盐酸存在下，用盐酸羟胺处理。

  DOI：

  10.1002/jhet.5570330612
• 作为产物：
  描述：

  4-methoxy-4-(4-nitrophenyl)-1,1,1-trichloro-3-buten-2-one 在 吡啶 、 盐酸羟胺 作用下， 以 甲醇 为溶剂， 70.0 ℃ 、220.0 kPa 条件下， 生成 3-(4-Nitro-phenyl)-5-trichloromethyl-4,5-dihydro-isoxazol-5-ol
  参考文献：
  名称：

  Microwave-assisted synthesis and antimicrobial activity of 5-trihalomethyl-3-arylisoxazoles

  摘要：

  A series of twelve 5-trihalomethyl-3-arylisoxazoles was synthesized and screened for antibacterial and antifungal activities. The compounds were synthesized from the cyclondensation of 1,1,1-trihalo-4-alkoxy-3-alken-2-ones [CX C-3(O)C(R-2)=C(R-1)OR, where X = Cl and F; R=Me; R-2=H; R-1=H, Me, F, Cl, Br, and NO2] with hydroxylamine hydrochloride through a rapid one-pot reaction via microwave irradiation. Some of the 5-trihalomethyl-3-arylisoxazoles exhibited good in vitro anti-Cryptococcus activity.

  DOI：

  10.1007/s00706-007-0849-1

文献信息

• Haloacetylated enol ethers. 7 . Synthesis of 3-aryl-5-trihalomethylisoxazoles and 3-aryl-5-hydroxy-5-trihalomethyl-4,5-dihydroisoxazoles
  作者：Marcos A. P. Martins、Geonir M. Siqueira、Giovani P. Bastos、Helio G. Bonacorso、Nilo Zanatta

  DOI：10.1002/jhet.5570330612

  日期：1996.11

  cyclocondensed with hydroxylamine hydrochloride to afford the 3-aryl-5-hydroxy-5-trihalomethyl-4,5-dihydroisoxazoles 3a-g, 4a-f in good yield. The dehydratation of compounds 3a-g with concentrated sulfuric acid, led the corresponding 3-aryl-5-trichloromethylisoxazoles 5a-g. An alternative one-pot procedure yields 3-aryl-5-trihalomethylisoxazoles 5,6a-g directly by cyclocondesation of 1,2a-g with hydroxylamine

  β-芳基-β-甲氧基乙烯基三卤甲基酮1a-g，2a-g [芳基= p -YC 6 H 4，其中Y = H，Me，OMe，F，Cl，Br，NO 2 ]与羟胺盐酸盐环缩合得到3-芳基-5-羟基-5-三卤甲基-4，5-二氢异恶唑3a-g，4a-f具有良好的收率。用浓硫酸使化合物3a-g脱水，得到相应的3-芳基-5-三氯甲基异恶唑5a-g。另一种一锅法直接通过1,2a-g的环缩构反应生成3-芳基-5-三卤代甲基异恶唑5,6a -g 在过量浓盐酸存在下，用盐酸羟胺处理。
• Microwave assisted synthesis of 5-hydroxy-5-trichloromethyl-4,5-dihydroisoxazoles
  作者：Marcos A.P Martins、Paulo Beck、Wilson Cunico、Claudio M.P Pereira、Adilson P Sinhorin、Rogério F Blanco、Rodrigo Peres、Helio G Bonacorso、Nilo Zanatta

  DOI：10.1016/s0040-4039(02)01555-1

  日期：2002.9

  A series of 13 5-hydroxy-5-trichloromethyl-4,5-dihydroisoxazoles have been synthesized in 78-96% yield by environmentally benign microwave induced techniques involving the cyclocondensation of 4-alkoxy-1,1,1-trichloro-3-alken-2-ones [CCl3C(O)C(R-2)=C(R-1)OR, where R-2=H, alkyl; R-1=H, alkyl, aryl and R=H, alkyl] with hydroxylamine using toluene as solvent. The advantages obtained by the use of microwave irradiation in relation to a classical method were demonstrated. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Microwave-assisted synthesis and antimicrobial activity of 5-trihalomethyl-3-arylisoxazoles
  作者：Marcos A. P. Martins、Pablo Machado、Luciana A. Piovesan、Alex F. C. Flores、Marli M. A. de Campos、Carolina Scheidt、Helio G. Bonacorso、Nilo Zanatta

  DOI：10.1007/s00706-007-0849-1

  日期：2008.8

  A series of twelve 5-trihalomethyl-3-arylisoxazoles was synthesized and screened for antibacterial and antifungal activities. The compounds were synthesized from the cyclondensation of 1,1,1-trihalo-4-alkoxy-3-alken-2-ones [CX C-3(O)C(R-2)=C(R-1)OR, where X = Cl and F; R=Me; R-2=H; R-1=H, Me, F, Cl, Br, and NO2] with hydroxylamine hydrochloride through a rapid one-pot reaction via microwave irradiation. Some of the 5-trihalomethyl-3-arylisoxazoles exhibited good in vitro anti-Cryptococcus activity.