3-Thiophen-2-yl-5-trichloromethyl-4,5-dihydro-isoxazol-5-ol

• 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-Thiophen-2-yl-5-trichloromethyl-4,5-dihydro-isoxazol-5-ol
• 英文别名: 3-(Thiophen-2-yl)-5-(trichloromethyl)-4,5-dihydro-1,2-oxazol-5-ol；3-thiophen-2-yl-5-(trichloromethyl)-4H-1,2-oxazol-5-ol
• 化学式: C₈H₆Cl₃NO₂S
• 分子量: 286.566
• InChiKey: DBBIOIVPFKAWMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  70.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-Thiophen-2-yl-5-trichloromethyl-4,5-dihydro-isoxazol-5-ol 在 硫酸 作用下， 反应 2.0h， 以82%的产率得到3-Thiophen-2-yl-5-trichloromethyl-isoxazole
  参考文献：
  名称：

  卤乙酰化烯醇醚，19：3-(2-噻吩基)-和 3-(2-呋喃基)-5-三卤代甲基取代唑的合成

  摘要：

  1,1,1-三氟[氯]-4-甲氧基-4-[2-噻吩基]-3-丁烯-2-酮和1,1,1-三氟[氯]-4-甲氧基-4-的杂环化报道了将[2-呋喃基]-3-丁烯-2-酮转化为异恶唑和吡唑衍生物作为新型三卤甲基化双环杂环。

  DOI：

  10.1055/s-2005-872140
• 作为产物：
  描述：

  (Z)-1,1,1-Trichloro-4-methoxy-4-thiophen-2-yl-but-3-en-2-one 在 盐酸羟胺 作用下， 以 甲醇 为溶剂， 以93%的产率得到3-Thiophen-2-yl-5-trichloromethyl-4,5-dihydro-isoxazol-5-ol
  参考文献：
  名称：

  卤乙酰化烯醇醚，19：3-(2-噻吩基)-和 3-(2-呋喃基)-5-三卤代甲基取代唑的合成

  摘要：

  1,1,1-三氟[氯]-4-甲氧基-4-[2-噻吩基]-3-丁烯-2-酮和1,1,1-三氟[氯]-4-甲氧基-4-的杂环化报道了将[2-呋喃基]-3-丁烯-2-酮转化为异恶唑和吡唑衍生物作为新型三卤甲基化双环杂环。

  DOI：

  10.1055/s-2005-872140

文献信息

• Structural investigations of 5-hydroxy-4,5-dihydroisoxazoles
  作者：Patrick T. Campos、Pablo Machado、Clarissa P. Frizzo、Dayse N. Moreira、Alexandre R. Meyer、Helio G. Bonacorso、Nilo Zanatta、Lucas C. Ducati、Roberto Rittner、Cláudio F. Tormena、Marcos A.P. Martins

  DOI：10.1016/j.molstruc.2011.09.051

  日期：2011.12

  The X-ray diffraction data determined for eight 3-(R-3), 4-(R-4), 4,4-(R-4/R-4') and/or 5-(R-5) 5-hydroxy-4,5-dihydroisoxazoles [where R-3 = Ph, R-4/R-4' = H/H, R-5 = CCl3 (1); R-3 = 4-Br-C6H4, R-4/R-4' = H/H, R-5 = CCl3 (2); R-3 = thien-2-yl, R-4/R-4' = H/H, R-5 = CCl3 (3); R-3 = Ph, R-4 = Ph, R-4' = OH, R-5 = Me (4); R-3 = Me, R-4/R-4' = N-OH, R-5 = Me (5); R-3 = CF3, R-4/R-4' = H/H, R-5 = CMe2CH2OH (6); R-3 = H, R-4 = 4-I-C6H4, R-4' = H, R-5 = 4-I-C6H4 (7): R-3/R-4 = -(CH2)(3)-, R-4' = H, R-5 = CF2CF2H (8);] are discussed. The crystalline structure of compounds 1-3 is described for the first time and crystalline structure of compounds 4-8 has already been described in literature. It was found that the supramolecular auto-organization of 1-8 is characterized by hydrogen bonds invariably involving the hemiacetal hydroxyl group. Compound 5 is the only exception, where the hydroxyl oxime group is the participant in the hydrogen bond. Compounds 4 and 8 present intermolecular contact between the hydroxyl group of the hemiacetal and the nitrogen atom of the 4,5-dihydroisoxazole ring. Compound 7 presents similar interaction, where the hydroxyl contact is with the oxygen atom of the 4,5-dihydroisoxazole ring. Moreover, the crystal structure of compound 6 was stabilized by O-H center dot center dot center dot O interaction between the hydroxyl group of hemiacetal and the hydroxyl group of the alcohol function attached at the 5-position of 4,5-dihydroisoxazole. The crystal structure of compounds 1-3, as described here for the first time, was similar to that of compounds 4 and 7, showing a hydrogen bond O(51)-H(51)center dot center dot center dot N(2) between the hydroxyl group and the nitrogen atom of the isoxazoline ring. This means that the crystal structure of these compounds was governed by hydrogen bonds O-H center dot center dot center dot N, involving the hydroxyl of the hemiacetal group and the nitrogen atom of the 4,5-dihydroisoxazole ring. This interaction is relatively robust, showing a pattern in the crystal packing. Compounds 1-3 also have their crystal stabilized by more weak interactions of type Cl center dot center dot center dot Cl, involving the chlorine atom of the trichloromethyl group. (C) 2011 Elsevier B.V. All rights reserved.
• Haloacetylated Enol Ethers, 19: Synthesis of 3-(2-Thienyl)- and 3-(2-Furyl)-5-trihalomethyl Substituted Azoles
  作者：Alex Flores、Sergio Brondani、Lucas Pizzuti、Marcos Martins、Nilo Zanatta、Helio Bonacorso、Darlene Flores

  DOI：10.1055/s-2005-872140

  日期：——

  Heterocyclization of 1,1,1-trifluoro[chloro]-4-methoxy-4-[2-tienyl]-3-buten-2-one and 1,1,1-trifluoro[chloro]-4-methoxy-4-[2-furyl]-3-buten-2-ones into isoxazoles and pyrazoles derivatives as a new type of trihalomethylated bicyclic heterocycles is reported.

  1,1,1-三氟[氯]-4-甲氧基-4-[2-噻吩基]-3-丁烯-2-酮和1,1,1-三氟[氯]-4-甲氧基-4-的杂环化报道了将[2-呋喃基]-3-丁烯-2-酮转化为异恶唑和吡唑衍生物作为新型三卤甲基化双环杂环。