3-(Trichloromethyl)-4,5,6,7-tetrahydro-2,1-benzoxazole | 169773-56-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(Trichloromethyl)-4,5,6,7-tetrahydro-2,1-benzoxazole
• CAS: 169773-56-2
• 化学式: C₈H₈Cl₃NO
• 分子量: 240.517
• InChiKey: RIUSXKXEIXOFER-UHFFFAOYSA-N

物化性质

• 熔点：
  174-177 °C(Solv: hexane (110-54-3))
• 沸点：
  308.1±37.0 °C(Predicted)
• 密度：
  1.470±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  26
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(Trichloromethyl)-4,5,6,7-tetrahydro-2,1-benzoxazole 在 硫酸 作用下， 生成 2,1-(4,5,6,7-四氢苯并)异恶唑-3-羧酸
  参考文献：
  名称：

  A convenient one-pot synthesis of 5-carboxyisoxazoles: trichloromethyl group as a carboxyl group precursor

  摘要：

  The one-pot synthesis of ten 5-carboxyisoxazoles from the cyclocondensation of beta-alkoxyvinyl trichloromethyl ketones [CCl3C(O)C(R-2)=C(R-1)OR, where R-1, R-2=H, Me and R=Me, Et] and 2-trichloroacetyl cyclohexanone with hydroxylamine is reported. This work shows that the trichloromethyl group attached to beta-alkoxyvinyl trichloromethyl ketones (a heterocyclic CCC building block) is an excellent carboxyl group precursor. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)02047-x
• 作为产物：
  描述：

  3-(trichloromethyl)-4,5,6,7-tetrahydro-3aH-2,1-benzoxazol-3-ol 在 硫酸 作用下， 反应 5.0h， 以82%的产率得到3-(Trichloromethyl)-4,5,6,7-tetrahydro-2,1-benzoxazole
  参考文献：
  名称：

  Martins, Marcos A. P.; Flores, Alex F. C.; Freitag, Rogerio, Journal of Heterocyclic Chemistry, 1995, vol. 32, # 3, p. 731 - 734

  摘要：

  DOI：

文献信息

• Synthesis and structure of new trichloromethyl-β-diketones — 5-Trichloromethylisoxazole and 5-isoxazolecarboxylic acid derivatives
  作者：Marcos A.P Martins、Sergio Brondani、Victor L Leidens、Darlene C Flores、Sidnei Moura、Nilo Zanatta、Manfredo Hörner、Alex FC Flores

  DOI：10.1139/v05-130

  日期：2005.8.1

  An improved method for the synthesis of a new series of trichloromethyl-β-diketones including 1,1,1-trichloropentan-2,4-dione (2a), 1,1,1-trichloro-3-methylhexan-2,4-dione (2b), 4,4,4-trichloro-1-phenylbutan-1,3-dione (2c), 4,4,4-trichloro-2-methyl-1-phenylbutan-1,3-dione (2d), 2-trichloroacetylcyclohexanone (2e), 4-tert-butylcyclohexanone (2f), 4-tert-butylcycloheptanone (2g), and 4-tert-butylcyclooctanone (2h) is reported. A multinuclear NMR study showed that β-dicarbonyl compounds 2b and 2d–2h are predominantly in the keto form and 2a and 2c are in the enol form. The trichloromethyl-β-diketones react with hydroxylamine hydrochloride leading to three sets of isoxazole derivatives.Key words: acetals, acylation, trichloromethyl-1,3-diketones, 2-trichloroacetylcycloalkanones, isoxazoles, cyclocondensation.

  一种改进的方法用于合成一系列新的三氯甲基-β-二酮，包括1,1,1-三氯戊二酮（2a）、1,1,1-三氯-3-甲基己二酮（2b）、4,4,4-三氯-1-苯基丁二酮（2c）、4,4,4-三氯-2-甲基-1-苯基丁二酮（2d）、2-三氯乙酰环己酮（2e）、4-叔丁基环己酮（2f）、4-叔丁基环庚酮（2g）和4-叔丁基环辛酮（2h）。多核NMR研究表明，β-二羰基化合物2b和2d至2h主要以酮形式存在，而2a和2c以烯醇形式存在。三氯甲基-β-二酮与盐酸羟胺反应，生成三组异噁唑衍生物。关键词：缩醛，酰化，三氯甲基-1,3-二酮，2-三氯乙酰环烷酮，异噁唑，环缩合。
• 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.
• Martins, Marcos A. P.; Flores, Alex F. C.; Freitag, Rogerio, Journal of Heterocyclic Chemistry, 1995, vol. 32, # 3, p. 731 - 734
  作者：Martins, Marcos A. P.、Flores, Alex F. C.、Freitag, Rogerio、Zanatta, Nilo

  DOI：——

  日期：——
• A convenient one-pot synthesis of 5-carboxyisoxazoles: trichloromethyl group as a carboxyl group precursor
  作者：Marcos A.P. Martins、Alex F.C. Flores、Giovani P. Bastos、Adilson Sinhorin、Helio G. Bonacorso、Nilo Zanatta

  DOI：10.1016/s0040-4039(99)02047-x

  日期：2000.1

  The one-pot synthesis of ten 5-carboxyisoxazoles from the cyclocondensation of beta-alkoxyvinyl trichloromethyl ketones [CCl3C(O)C(R-2)=C(R-1)OR, where R-1, R-2=H, Me and R=Me, Et] and 2-trichloroacetyl cyclohexanone with hydroxylamine is reported. This work shows that the trichloromethyl group attached to beta-alkoxyvinyl trichloromethyl ketones (a heterocyclic CCC building block) is an excellent carboxyl group precursor. (C) 2000 Elsevier Science Ltd. All rights reserved.