3-phenyl-5-acetoxy-4,5-dihydroisoxazole | 7064-07-5

• 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-phenyl-5-acetoxy-4,5-dihydroisoxazole
• 英文别名: 5-acetoxy-4,5-dihydro-3-phenyl-isoxazole；3-phenyl-4,5-dihydroisoxazol-5-yl acetate；5-acetoxy-3-phenyl-4,5-dihydro-isoxazole；acetic acid-(3-phenyl-4,5-dihydro-isoxazol-5-yl ester)；Essigsaeure-(3-phenyl-4,5-dihydro-isoxazol-5-ylester)；3-Phenyl-5-acetoxy-2-isoxazoline；(3-phenyl-4,5-dihydro-1,2-oxazol-5-yl) acetate
• CAS: 7064-07-5
• 化学式: C₁₁H₁₁NO₃
• 分子量: 205.213
• InChiKey: VYVLQNWMMRLTQQ-UHFFFAOYSA-N

物化性质

• 熔点：
  88-89 °C
• 沸点：
  294.6±50.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  47.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-phenyl-5-acetoxy-4,5-dihydroisoxazole 生成 3-苯基异恶唑
  参考文献：
  名称：

  异恶唑化学研究。二、来自 Δ2-isoxazolin-5-ols 的异恶唑及其醋酸盐

  摘要：

  通过腈氧化物与乙酸乙烯酯或乙酸异丙烯酯的 1,3-偶极环加成反应制备了各种 3-取代-5-乙酰氧基-Δ2-异恶唑啉。这些化合物在加热时很容易以高产率分别转化为 3-取代的异恶唑或 3-取代的 5-甲基异恶唑。在甲醇中用氢氧化钠处理 3-取代-5-乙酰氧基-Δ2-异恶唑啉在酸化后产生稳定的 Δ2-异恶唑啉-5-醇。这些化合物也可以通过单独加热或在亚硫酰氯的存在下更好地转化为 3-取代的异恶唑。讨论了这些化合物的核磁共振谱。

  DOI：

  10.1139/v70-075
• 作为产物：
  描述：

  苯甲醛肟 在 chloroamine-T 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 0.03h， 生成 3-phenyl-5-acetoxy-4,5-dihydroisoxazole
  参考文献：
  名称：

  Lokanatha Rai; Hassner, Alfred, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1997, vol. 36, # 3, p. 242 - 245

  摘要：

  DOI：

文献信息

• A Convenient Preparative Method of Nitrile Oxides by the Dehydration of Primary Nitro Compounds with Ethyl Chloroformate or Benzenesulfonyl Chloride in the Presence of Triethylamine
  作者：Tomio Shimizu、Yoshiyuki Hayashi、Hiroshi Shibafuchi、Kazuhiro Teramura

  DOI：10.1246/bcsj.59.2827

  日期：1986.9

  nitrile oxides (MeOCOC≡N→O, PhC≡N→O, and EtC≡N→O) were effectively generated in situ by dehydration of the corresponding primary nitro compounds (RCH2NO2) with PhSO2Cl or ClCOOEt in the presence of triethylamine. Various cycloadducts were prepared by the reaction of them with dipolarophiles. Some advantages of these methods are described in comparison with other known methods.

  在三乙胺的存在下，通过用 PhSO2Cl 或 ClCOOEt 使相应的初级硝基化合物 (RCH2NO2) 脱水，原位有效地生成了三种腈氧化物（MeOCOC≡N→O、PhC≡N→O 和 EtC≡N→O）。各种环加合物是通过它们与偶极试剂反应制备的。与其他已知方法相比，描述了这些方法的一些优点。
• <i>O</i>-Ethoxycarbonyl Hydroximoyl Chloride as Nitrile Oxide Precursor
  作者：Tomio Shimizu、Yoshiyuki Hayashi、Nobuhiro Furukawa、Kazuhiro Teramura

  DOI：10.1246/bcsj.64.318

  日期：1991.1

  O-Ethoxycarbonyl hydroximoyl chloride serves as a stable precursor for nitrile oxide and is converted into the 1,3-dipole when heated under reflux in pyridine.

  O-乙氧羰基羟肟酰氯作为腈氧化物的稳定前体，在吡啶中回流加热时转化为 1,3-偶极子。
• Lead tetraacetate oxidation of aldoximes
  作者：G. Just、K. Dahl

  DOI：10.1016/s0040-4020(01)96322-7

  日期：1968.1

  The lead tetraacetate oxidation of aldoximes at low temperature has benn studied. Oxidation of aliphatic and aromatic syn-aldoximes affords nitrile oxides. Aliphatic anti-aldoximes lead to dimeric 1-acetoxy-1-nitroso-alkanes and secondary products. Aromatic anti-aldoximes afford arylaldazine-bis-N-oxides which decompose on heating to nitrile oxides and aldoximes. Mechanisms are proposed which require

  已经研究了在低温下醛肟的四乙酸铅氧化。脂族和芳族合成醛肟的氧化提供了腈氧化物。脂肪族抗醛肟导致二聚的1-乙酰氧基-1-亚硝基-烷烃和副产物。芳族抗醛肟类化合物提供芳基aldazine - bis -N-氧化物，该化合物在加热时分解为腈氧化物和醛肟类。被提出的机制需要亚氨氧基自由基如在氧化的中间体反-aldoximes，而氧化顺-aldoximes出现协调一致地进行。
• An Improved Method for Preparation of Nitrile Oxides from Nitroalkanes for In Situ Dipolar Cycloadditions
  作者：Yochai Basel、Alfred Hassner

  DOI：10.1055/s-1997-1181

  日期：1997.3

  A new method has been found for generation of nitrile oxides in situ from nitroalkanes under mild conditions. Thus, reaction of nitroalkanes 1 with di-tert-butyl dicarbonate (2) and 4-dimethyl-aminopyridine (3) as catalyst in the presence of dipolarophiles at room temperature afforded cycloadducts (e.g. 5,6, and 7) in improved yields compared to known methods. Solvent effects were also noted.

  已发现一种新方法，可以在温和条件下从硝基烷烃原位生成腈氧化物。因此，将硝基烷烃1与二叔丁基二羧酸酯（2）和含有催化剂的4-二甲基氨基吡啶（3）在室温下与极性偶极体反应，得到了环加成产物（例如5、6和7），其产率相比已知方法有了改善。同时也观察到了溶剂效应。
• Nitrile Oxide 1,3-Dipolar Cycloaddition by Dehydration of Nitromethane Derivatives Under Continuous Flow Conditions
  作者：Malte Brasholz、Simon Saubern、G. Paul Savage

  DOI：10.1071/ch11079

  日期：——

  Aliphatic nitrile oxides were generated in situ, by dehydration of terminal nitro compounds, and reacted with dipolarophiles using continuous flow techniques to afford substituted isoxazolines. The yields of cycloadducts were comparable with traditional flask-based reactions but reaction times were much shorter. In-line scavenger cartridges conveniently removed by-products and unreacted reagents to give almost pure crude products. The process was demonstrated up to gram scale.

  通过末端硝基化合物的脱水，在原位生成脂肪族腈氧化物，并利用连续流技术与二极性化合物反应，生成取代的异噁唑类化合物。环加载产物的产量与传统的烧瓶反应相当，但反应时间更短。在线清除剂滤筒可方便地清除副产物和未反应试剂，从而得到几乎纯净的粗产品。该工艺已在克级规模上得到验证。