3-bromomethyl-5-hydroxy-5-trichloromethyl-4,5-dihydroisoxazole | 401512-67-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: 3-bromomethyl-5-hydroxy-5-trichloromethyl-4,5-dihydroisoxazole
• 英文别名: 3-(bromomethyl)-5-(trichloromethyl)-4H-1,2-oxazol-5-ol
• CAS: 401512-67-2
• 化学式: C₅H₅BrCl₃NO₂
• 分子量: 297.363
• InChiKey: YKHIEDOZOLDLAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  41.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-bromomethyl-5-hydroxy-5-trichloromethyl-4,5-dihydroisoxazole 在 硫酸 作用下， 反应 16.0h， 以73%的产率得到3-bromomethyl-5-trichloromethylisoxazole
  参考文献：
  名称：

  4-Methoxy-1,1,1-trihalo-3-alken-2-ones 和 5-Methoxy-1,1,1,2,2-pentafluoro-4-hexen-2-one 的区域特异性烯丙基单溴化和二溴化, 及其在杂环合成中的应用

  摘要：

  一系列十二个 5-bromo[5,5-dibromo]-4-methoxy-1,1,1-trihalo-3-alken-2-ones 5a-d、6a-d、7a、9a、10a 和 6- bromo-5-methoxy-1,1,1,2,2-pentafluoro-4-hexen-2-one (8a) 通过区域特异性烯丙基溴化 4- meihoxy-1,1,1-trihalo-3-alken-2-ones la-d, 2a-d, 3a or 5-methoxy-1,1,1,2,2-pentafluoro-4-hexen-2-one (4a) 分别用溴，然后加入吡啶。还报道了化合物 5-10 在杂环合成中的用途。

  DOI：

  10.1055/s-2002-35224
• 作为产物：
  描述：

  5-bromo-1,1,1-trichloromethyl-4-methoxy-3-penten-2-one 在 吡啶 、 盐酸羟胺 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以84%的产率得到3-bromomethyl-5-hydroxy-5-trichloromethyl-4,5-dihydroisoxazole
  参考文献：
  名称：

  A Convenient Synthesis of 5-Trichloromethyl-5-hydroxy-3-heteroalkyl-4,5-dihydroisoxazoles

  摘要：

  本研究基于 5-杂烷基-1,1,1-三氯-4-甲氧基-3-戊烯并[己烯]-2-酮 1a-g、2a-g 与羟胺的环缩合反应，开发了一种获得一系列 3-杂烷基-4,5-二氢异噁唑的合成策略。此外，还描述了以良好收率制备 1,1,1-三氯-5-异烷基-4-甲氧基-3-戊烯并[己烯]-2-酮的方法。

  DOI：

  10.1055/s-2001-17701

文献信息

• A Convenient Synthesis of 5-Trichloromethyl-5-hydroxy-3-heteroalkyl-4,5-dihydroisoxazoles
  作者：Marcos A. P. Martins、Adilson P. Sinhorin、Nilo E. K. Zimmermann、Nilo Zanatta、Helio G. Bonacorso、Giovani P. Bastos

  DOI：10.1055/s-2001-17701

  日期：——

  A synthetic strategy to obtain a series of 3-heteroalkyl-4,5-dihydroisoxazoles, which is based on the cyclocondensation reaction of 5-heteroalkyl-1,1,1-trichloro-4-methoxy-3-penten[hexen]-2-ones 1a-g, 2a-g with hydroxylamine has been developed. The preparation of 1,1,1-trichloro-5-heteroalkyl-4-methoxy-3-penten[hexen]-2-ones in good yields is also described.

  本研究基于 5-杂烷基-1,1,1-三氯-4-甲氧基-3-戊烯并[己烯]-2-酮 1a-g、2a-g 与羟胺的环缩合反应，开发了一种获得一系列 3-杂烷基-4,5-二氢异噁唑的合成策略。此外，还描述了以良好收率制备 1,1,1-三氯-5-异烷基-4-甲氧基-3-戊烯并[己烯]-2-酮的方法。
• Regiospecific Allylic Mono- and Dibromination of 4-Methoxy-1,1,1-trihalo-3-alken-2-ones and 5-Methoxy-1,1,1,2,2-pentafluoro-4-hexen-2-one, and their Applications to the Synthesis of Heterocycles
  作者：Marcos A. Martins、Adilson P. Sinhorin、Adriano da Rosa、Alex F. Flores、Arci D. Wastowski、Claudio M. P. Pereira、Darlene C. Flores、Paulo Beck、Rogerio A. Freitag、Sergio Brondani、Wilson Cunico、Helio G. Bonacorso、Nilo Zanatta

  DOI：10.1055/s-2002-35224

  日期：——

  (8a) were synthesized in high purity and good yields (70-95%) by the regiospecific allylic bromination of 4-meihoxy-1,1,1-trihalo-3-alken-2-ones la-d, 2a-d, 3a or 5-methoxy-1,1,1,2,2-pentafluoro-4-hexen-2-one (4a), respectively, with bromine followed by addition of pyridine. The usefulness of compounds 5-10 in heterocyclic synthesis is also reported.

  一系列十二个 5-bromo[5,5-dibromo]-4-methoxy-1,1,1-trihalo-3-alken-2-ones 5a-d、6a-d、7a、9a、10a 和 6- bromo-5-methoxy-1,1,1,2,2-pentafluoro-4-hexen-2-one (8a) 通过区域特异性烯丙基溴化 4- meihoxy-1,1,1-trihalo-3-alken-2-ones la-d, 2a-d, 3a or 5-methoxy-1,1,1,2,2-pentafluoro-4-hexen-2-one (4a) 分别用溴，然后加入吡啶。还报道了化合物 5-10 在杂环合成中的用途。
• Synthesis in Water and Antimicrobial Activity of 5-Trichloromethyl-4,5-dihydroisoxazoles
  作者：Alex F. C. Flores、Luciana A. Piovesan、Alynne A. Souto、Mariano A. Pereira、Marcos A. P. Martins、Tatiane L. Balliano、Givanildo S. da Silva

  DOI：10.1080/00397911.2012.706349

  日期：2013.9.2

  Two series of 5-trichloromethylisoxazoles were synthesized from the cyclocondensation of 1,1,1-trichloro-4-methoxy-3-alken-2-ones [Cl3CC(O)C(R-2)=C(R-1)OMe, where R-1=H, Me, Et, Pr, iso-Pr, cyclo-Pr, Bu, terc-Bu, CH2Br, CHBr2, CH(Me)SMe, (CH2)(2)Ph, and Ph, and R-2=H; R-1=H and R-2=Me and Et; R-1 and R-2=-(CH2)(4)- and -(CH2)(5)-; and R-1=Et and Ph and R-2=Me] with hydroxylamine hydrochloride through a rapid one-pot reaction in water. The 5-trichloromethyl-4,5-dihydroisoxazoles were aromatized by reaction with concentrated sulfuric acid to obtain the respective 5-trichloromethylisoxazoles. Their structures were confirmed by elemental analysis, H-1/C-13 nuclear magnetic resonance, and electron impact mass spectroscopy. Crystal structure analysis for 5-triclhoromethyl-5-hydroxy-3-propyl-4,5-dihydroisoxazole (2d) and 5-trichloromethyl-5-hydroxy-3,4-hexamethylene-4,5-dihydroisoxazole (2o) is presented. The antimicrobial activities of the 5-trichloromethyl-4,5-dihydroisoxazole derivatives were examined using the standard twofold dilution method against Gram-positive bacteria (Staphylococcus aureus), Gram-negative bacteria (Escherichia coli and Pseudomonas aeruginosa), and yeasts (Candida spp. and Cryptococcus neoformans). All of the tested 5-trichloromethyldihydroisoxazoles exhibited antibacterial and antifungal activities at the tested concentrations. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.

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