(3-benzoyl-4,5-dihydro-1,2-oxazol-5-yl)acetonitrile | 112779-15-4

• 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-benzoyl-4,5-dihydro-1,2-oxazol-5-yl)acetonitrile
• 英文别名: 3-benzoyl-5-cyanomethyl-4,5-dihydroisoxazole；2-(3-Benzoyl-4,5-dihydro-1,2-oxazol-5-yl)acetonitrile
• CAS: 112779-15-4
• 化学式: C₁₂H₁₀N₂O₂
• 分子量: 214.224
• InChiKey: HNSRHHGCVHFLPA-UHFFFAOYSA-N

物化性质

• 沸点：
  392.9±34.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  62.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  烯丙基腈 、 苯甲酰硝基甲烷 在 silica gel-supported polyphosphoric acid 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以99%的产率得到(3-benzoyl-4,5-dihydro-1,2-oxazol-5-yl)acetonitrile
  参考文献：
  名称：

  Application of silica gel-supported polyphosphoric acid (PPA/SiO2) as a reusable solid acid catalyst to the synthesis of 3-benzoylisoxazoles and isoxazolines

  摘要：

  3-Benzoylisoxazoles were synthesized by the reaction of alkynes and benzoylnitromethane using silica gel-supported polyphosphoric acid (PPA/SiO2). This reaction provides a convenient, efficient, and reusable synthetic method of isoxazole derivatives. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.10.038

文献信息

• Aroylnitrile oxide cyclizations. 2. Synthesis of (3-aroylisoxazol-5-yl)alkanoic acids
  作者：John J. Tegeler、Craig J. Diamond

  DOI：10.1002/jhet.5570240331

  日期：1987.5

  Intermolecular cyclization of 1,3-dipolar aroylnitrile oxides to terminal alkynols followed by phase transfer catalyzed oxidation provided a short, convenient route to several novel (3-aroylisoxazol-5-yl)alkanoic acids.

  1，3-偶极芳族腈氧化物的分子间环化成末端炔醇，然后进行相转移催化氧化，提供了一条短而方便的途径来制备几种新型的（3-芳基异恶唑-5-基）链烷酸。
• Formation of isoxazole derivatives via nitrile oxide using ammonium cerium nitrate (CAN): a novel one-pot synthesis of 3-acetyl- and 3-benzoylisoxazole derivatives
  作者：Ken-ichi Itoh、C.Akira Horiuchi

  DOI：10.1016/j.tet.2003.11.088

  日期：2004.2

  4-diacetyl-1,2,5-oxadiazole 2-oxide) as the dimer of nitrile oxide. Moreover, it was found that yields of isoxazole derivatives were improved using ammonium cerium(III) nitrate tetrahydrate ((NH4)2Ce(NO3)5·4H2O, CAN(III))-formic acid. The reaction mechanisms based on nitration and formation of nitrile oxide mediated by CAN(IV) or CAN(III) from acetone or acetophenone are also proposed.

  烯烃和炔烃与硝酸铈铈（IV）铵（（NH 4）2 Ce（NO 3）6，CAN（IV））在丙酮中的回流下反应，得到相应的3-乙酰基-4,5-二氢异恶唑和3-乙酰异恶唑衍生物。在苯乙酮的情况下，获得了3-苯甲酰基-4，5-二氢异恶唑和3-苯甲酰基异恶唑衍生物。丙酮与CAN（IV）反应，得到相应的呋喃烷（3,4-二乙酰基-1,2,5-恶二唑2-氧化物），为一氧化二氮的二聚体。此外，发现使用四水合硝酸铈铈（III）（（NH 4）2 Ce（NO 3）5 ·4H 2O，CAN（III））-甲酸。还提出了基于硝化反应并由丙酮或苯乙酮通过CAN（IV）或CAN（III）介导形成一氧化氮的反应机理。
• Method for manufacturing isoxazole derivative or dihydroisoxazole derivative
  申请人：Horiuchi Akira C.

  公开号：US20060247288A1

  公开（公告）日：2006-11-02

  There is provided with a method for manufacturing an isoxazole derivative at a high yield and without discharging waste products, and a novel isoxazole derivative. An isoxazole derivative expressed by Formula (8) is produced by reacting a 1-alkyne compound expressed by Formula (7) with iron(III) nitrate in the presence of acetone or acetophenone: (where R 1 is an alkyl, cycloalkyl, phenyl, or other such group); and (where R 2 is a methyl or a phenyl).

  提供了一种制造异噁唑衍生物的方法，可以高产率地制造而不排放废物，并提供了一种新颖的异噁唑衍生物。通过在丙酮或苯乙酮存在下，将式（7）表示的1-炔基化合物与硝酸铁（III）反应，可以制备式（8）表示的异噁唑衍生物：（其中R1是烷基、环烷基、苯基或其他类似基团）；以及（其中R2是甲基或苯基）。
• A novel one-pot synthesis of 3-acetyl- and 3-benzoylisoxazole derivatives using ammonium cerium nitrate (CAN)
  作者：Ken-ichi Itoh、Shigeo Takahashi、Tetsuya Ueki、Takashi Sugiyama、T.Tomoyoshi Takahashi、C.Akira Horiuchi

  DOI：10.1016/s0040-4039(02)01612-x

  日期：2002.9

  (several alkenes and alkynes) with ammonium cerium(IV) nitrate ((NH4)2Ce(NO3)6, CAN(IV)) in acetone under reflux gave 3-acetylisoxazole derivatives. In the case of acetophenone, 3-benzoylisoxazole derivatives were obtained. Moreover, it was found that yields of isoxazole derivatives were improved using ammonium cerium(III) nitrate tetrahydrate ((NH4)2Ce(NO3)5·4H2O, CAN(III))–formic acid.

  双极性亲和剂（几种烯烃和炔烃）与硝酸铈铈（Ⅳ）（（NH 4）2 Ce（NO 3）6，CAN（Ⅳ））在丙酮中在回流下反应，得到3-乙酰基异恶唑衍生物。在苯乙酮的情况下，获得了3-苯甲酰基异恶唑衍生物。此外，发现使用四水合硝酸铈铈（III）铵（（NH 4）2 Ce（NO 3）5 ·4H 2 O，CAN（III））-甲酸可提高异恶唑衍生物的产率。
• A Convenient and Efficient One-Pot Synthesis of 3-Acylisoxazoles Using Iron(III) Salts
  作者：C. Akira Horiuchi、Ken-ichi Itoh、Hiroshi Sakamaki、Noriko Nakazato、Atsuo Horiuchi、Ernst Horn

  DOI：10.1055/s-2005-916041

  日期：——

  by the reaction of alkenes or alkynes with ketones (acetone or acetophenone), as both a reagent and the solvent, by three methods: iron(lll) nitrate under reflux, iron(III) salt-nitrogen dioxide (NO;) at room temperature, and iron(III) nitrate under microwave irradiation (MW).

  3-酰基异恶唑是通过烯烃或炔烃与酮（丙酮或苯乙酮）反应合成的，既作为试剂又作为溶剂，通过三种方法合成：硝酸铁（III）在回流下，铁（III）盐-二氧化氮（NO ;) 在室温下，以及在微波辐射 (MW) 下的硝酸铁 (III)。