3-(4-chlorophenyl)-4,5-dihydroisoxazole-5-carbonitrile | 1173119-75-9

• 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-(4-chlorophenyl)-4,5-dihydroisoxazole-5-carbonitrile
• 英文别名: 3-(4-chlorophenyl)-4,5-dihydro-1,2-oxazole-5-carbonitrile
• CAS: 1173119-75-9
• 化学式: C₁₀H₇ClN₂O
• 分子量: 206.631
• InChiKey: ZXECSZDWMQSGCW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  45.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  在 吡啶 、 甲基磺酰氯 作用下， 反应 3.0h， 以98%的产率得到3-(4-chlorophenyl)-4,5-dihydroisoxazole-5-carbonitrile
  参考文献：
  名称：

  Iminoxyl Radical-Promoted Dichotomous Cyclizations: Efficient Oxyoximation and Aminooximation of Alkenes

  摘要：

  A novel iminoxyl radical-involved metal-free approach to vicinal oxyoximation and aminooximation of unactivated alkenes is developed. This method utilizes the dichotomous reactivity of the iminoxyl radical to furnish a general difunctionalization on alkenes using simple tert-butyl nitrite (TBN) as the iminoxyl radical initiator as well the carbon radical trap. By using this protocol, oxime featured 4,5-dihydroisoxazoles and cyclic nitrones were facilely prepared from beta,gamma- and gamma,delta-unsaturated ketoximes, respectively.

  DOI：

  10.1021/ol502258n

文献信息

• Efficient synthesis of isoxazoles and isoxazolines from aldoximes using Magtrieve™ (CrO2)
  作者：Sandeep Bhosale、Santosh Kurhade、Uppuleti Viplava Prasad、Venkata P. Palle、Debnath Bhuniya

  DOI：10.1016/j.tetlet.2009.04.073

  日期：2009.7

  Treatment of aldoximes 1 with Magtrieve™ (CrO2) in presence of dipolarophile 3 or 4, furnished a variety of isoxazolines 5a–u and isoxazoles 6a–q as 1,3-dipolar cycloaddition (1,3-DC) products (38 examples; 63–90% isolated yields). In situ formation of a nitrile oxide intermediate was confirmed through isolation of the dimerization product furoxane 2a in absence of any dipolarophile. The methodology

  在存在偶极亲和剂3或4的情况下，用Magtrieve ™（CrO 2）处理醛肟1，提供了各种异恶唑啉5a–u和异恶唑6a–q作为1,3-偶极环加成（1,3-DC）产品（38个例子） ； 63–90％的独立收益率）。通过在不存在任何双亲性物质的情况下分离二聚产物呋喃烷2a来确认一氧化氮中间体的原位形成。该方法已扩展到分子内一氧化氮环加成（INOC）反应，以获得高度有用的7-8色烷衍生物（分离产率为75-80％）。Magtrieve ™作为用于1,3-DC反应的新试剂，它具有出色的底物通用性，同时还表现出对敏感保护基和富电子官能团的耐受性。
• Koser’s Reagent Mediated Oxidation of Aldoximes: Synthesis of Isoxazolines by 1,3-Dipolar Cycloadditions
  作者：Rama Krishna Peddinti、Rajnish Budhwan、Megha Rawat

  DOI：10.1055/s-0042-1752403

  日期：——

  approach for the synthesis of isoxazoline derivatives is reported. This protocol involves 1,3-dipolar cycloaddition between in situ generated nitrile oxides from the corresponding aldoximes using [hydroxy(tosyloxy)iodo]benzene (HTIB, Koser’s reagent) and maleimides, styrene and acrylonitrile. The described methodology is very attractive as it is operationally simple, has broad scope, and does not require

  报道了一种用于合成异恶唑啉衍生物的无金属和无碱、稳健且方便的方法。该协议涉及 1，3-偶极环加成，使用 [羟基（甲苯磺酰氧基）碘] 苯（HTIB，Koser 试剂）和马来酰亚胺、苯乙烯和丙烯腈从相应的醛肟原位生成的腈氧化物之间。所描述的方法非常有吸引力，因为它操作简单，范围广泛，并且不需要任何碱、金属或其他添加剂。
• Iminoxyl Radical-Promoted Dichotomous Cyclizations: Efficient Oxyoximation and Aminooximation of Alkenes
  作者：Xie-Xue Peng、Yun-Jing Deng、Xiu-Long Yang、Lin Zhang、Wei Yu、Bing Han

  DOI：10.1021/ol502258n

  日期：2014.9.5

  A novel iminoxyl radical-involved metal-free approach to vicinal oxyoximation and aminooximation of unactivated alkenes is developed. This method utilizes the dichotomous reactivity of the iminoxyl radical to furnish a general difunctionalization on alkenes using simple tert-butyl nitrite (TBN) as the iminoxyl radical initiator as well the carbon radical trap. By using this protocol, oxime featured 4,5-dihydroisoxazoles and cyclic nitrones were facilely prepared from beta,gamma- and gamma,delta-unsaturated ketoximes, respectively.