4,5-Dichlor-3-phenyl-isoxazol | 62847-67-0

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 4,5-Dichlor-3-phenyl-isoxazol
• 英文别名: 4,5-dichloro-3-phenyl-isoxazole；4,5-Dichloro-3-phenyl-1,2-oxazole
• CAS: 62847-67-0
• 化学式: C₉H₅Cl₂NO
• 分子量: 214.051
• InChiKey: NUGLOJKOPOONBY-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：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  4,5-Dichlor-3-phenyl-isoxazol 以60%的产率得到
  参考文献：
  名称：

  CARR J. B.; DURHAM H. G.; HASS D. K., J. MED. CHEM. , 1977, 20, NO 7, 934-939

  摘要：

  DOI：
• 作为产物：
  描述：

  5-甲氧基-3-苯基异恶唑 在 盐酸 、 磺酰氯 、 三乙胺 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 4,5-Dichlor-3-phenyl-isoxazol
  参考文献：
  名称：

  Isoxazole anthelmintics

  摘要：

  A series of 3-halo-5-phenyl- and 3-phenyl-5-haloisoxazoles has demonstrated anthelmintic activity at doses ranging from 16 to 500 mg/kg orally against the rat roundworm, Nippostrongylus braziliensis. In the 5-phenyl series a halogen at the 3 position of the isoxazole ring was required for activity. However, in the 3-phenyl series activity was maintained after replacement of the 5-halogen with certain alkoxyl, thioalkoxyl, or amino groups. The 3-phenyl and 5-phenyl series apparently are not acting biologically at a common receptor site. Synthetic methods and structure-activity relationships are discussed.

  DOI：

  10.1021/jm00217a014

文献信息

• Gold vs Light: Chemodivergent Reactivity of Diazoesters toward 2<i>H</i>-Azirine-2-carboxylic Acids
  作者：Gleb D. Titov、Grigory I. Antonychev、Mikhail S. Novikov、Alexander F. Khlebnikov、Elizaveta V. Rogacheva、Liudmila A. Kraeva、Nikolai V. Rostovskii

  DOI：10.1021/acs.orglett.3c00823

  日期：2023.4.21

  reaction is N-selective and produces 1,3-oxazin-6-ones, whereas a blue light activation leads to O–H insertion products, azirine-2-carboxylic esters. The observed chemodivergence is explained by the metal-bound and metal-free carbenes exhibiting different electronic properties in these reactions. In addition, a high antibacterial potential of the 1,3-oxazin-6-ones synthesized is shown.

  证明了重氮化合物对 azirine-2-羧酸的正交反应性随反应条件的变化而变化。金催化的反应具有 N-选择性并产生 1,3-oxazin-6-ones，而蓝光激活会导致 O-H 插入产物 azirine-2-carboxylic esters。观察到的化学差异可以用在这些反应中表现出不同电子特性的金属结合和无金属卡宾来解释。此外，合成的 1,3-oxazin-6-ones 具有很高的抗菌潜力。
• Trading Symmetry for Stereoinduction in Tetradentate, non‐<i>C</i>₂‐Symmetric Fe(II)‐Complexes for Asymmetric Catalysis
  作者：Philipp S. Steinlandt、Marcel Hemming、Xiulan Xie、Sergei I. Ivlev、Eric Meggers

  DOI：10.1002/chem.202300267

  日期：2023.6.7

  A series of C1-symmetric bench-stable stereogenic-at-iron complexes comprising a linear, tetradentate ligand scaffold are introduced. The possibility of lowering the overall symmetry is scrutinized for an enantioselective ring-contraction of isoxazoles to furnish chiral 2H-azirines under open-flask conditions with the products serving as useful building blocks to access α-disubstituted α-amino acid

  介绍了一系列包含线性四齿配体支架的 C 1对称稳定型铁立体异构复合物。降低整体对称性的可能性被仔细检查异恶唑的对映选择性缩环以在开放烧瓶条件下提供手性 2 H-氮杂环丙烷，产物用作获得 α-二取代的 α-氨基酸衍生物的有用构建单元。
• Isoxazole anthelmintics
  作者：John B. Carr、Harry G. Durham、D. Kendall Hass

  DOI：10.1021/jm00217a014

  日期：1977.7

  A series of 3-halo-5-phenyl- and 3-phenyl-5-haloisoxazoles has demonstrated anthelmintic activity at doses ranging from 16 to 500 mg/kg orally against the rat roundworm, Nippostrongylus braziliensis. In the 5-phenyl series a halogen at the 3 position of the isoxazole ring was required for activity. However, in the 3-phenyl series activity was maintained after replacement of the 5-halogen with certain alkoxyl, thioalkoxyl, or amino groups. The 3-phenyl and 5-phenyl series apparently are not acting biologically at a common receptor site. Synthetic methods and structure-activity relationships are discussed.
• CARR J. B.; DURHAM H. G.; HASS D. K., J. MED. CHEM. <JMCM-AR>, 1977, 20, NO 7, 934-939
  作者：CARR J. B.、 DURHAM H. G.、 HASS D. K.

  DOI：——

  日期：——