1-(2-chlorophenyl)but-3-en-1-one oxime | 1574316-74-7

• 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: 1-(2-chlorophenyl)but-3-en-1-one oxime
• CAS: 1574316-74-7
• 化学式: C₁₀H₁₀ClNO
• 分子量: 195.648
• InChiKey: FTWNWCRXDVYKOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.09
• 重原子数：
  13.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  32.59
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-(2-chlorophenyl)but-3-en-1-one oxime 在 叠氮基三甲基硅烷 、 copper diacetate 、 sodium acetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以63%的产率得到5-(azidomethyl)-3-(2-chlorophenyl)-4,5-dihydroisoxazole
  参考文献：
  名称：

  Copper-Catalyzed Oxyazidation of Unactivated Alkenes: A Facile Synthesis of Isoxazolines Featuring an Azido Substituent

  摘要：

  A novel and efficient Cu(OAc)(2)-catalyzed oxyazidation of unactivated alkenes was developed. The reactions are easy to conduct, occur under mild conditions, and form azido-substituted isoxazolines in good yields.

  DOI：

  10.1021/ol403687k
• 作为产物：
  描述：

  1-(2-氯苯基)-3-丁烯-1-醇 在 Jones reagent 、 盐酸羟胺 、 sodium acetate 作用下， 以 乙醚 、 乙醇 、 水 为溶剂， 反应 1.0h， 生成 1-(2-chlorophenyl)but-3-en-1-one oxime
  参考文献：
  名称：

  铜介导的亚烷基肟与亚磺酸钠的氧羰基磺化反应：具有砜取代基的异恶唑啉的简便合成

  摘要：

  开发了新型和有效的Cu（OAc）2介导的用磺酸钠的烯基肟的氧磺酰化反应。该反应易于进行，在温和条件下发生，并且形成范围广泛的...

  DOI：

  10.1039/c7cc00090a

文献信息

• Oxime-Mediated Facile Access to 5-Methylisoxazoles and Applications in the Synthesis of Valdecoxib and Oxacillin
  作者：Kui-Yong Dong、Hai-Tao Qin、Xing-Xing Bao、Feng Liu、Chen Zhu

  DOI：10.1021/ol502246t

  日期：2014.10.17

  A palladium-catalyzed efficient synthesis of 5-methylisoxazoles via oxime-mediated functionalization of unactivated olefins is described. The reaction affords a variety of 5-methylisoxazoles in moderate to good yields. To further demonstrate the utility of the method, the rapid synthesis of valdecoxib and oxacillin is reported.

  描述了通过肟介导的未活化烯烃的钯催化的5-甲基异恶唑的有效合成。该反应以中等至良好的产率提供了多种5-甲基异恶唑。为了进一步证明该方法的实用性，报道了伐地昔布和奥沙西林的快速合成。
• Access to Cyano-Containing Isoxazolines via Copper-Catalyzed Domino Cyclization/Cyanation of Alkenyl Oximes
  作者：Fei Meng、Honglin Zhang、Kang Guo、Jiayue Dong、Ai-Min Lu、Yingguang Zhu

  DOI：10.1021/acs.joc.7b02133

  日期：2017.10.6

  A highly efficient copper-catalyzed cyclization/cyanation cascade of unactivated olefins bearing oximes is described. A variety of cyano-containing isoxazolines have been obtained in high yields with cheap Cu(NO3)2·3H2O as the catalyst and TMSCN as the non-metallic cyanide source. The present method provides a mild, simple, and practical access to cyano-substituted isoxazolines and is amenable to gram

  描述了带有肟的未活化烯烃的高效铜催化的环化/氰化级联反应。以廉价的Cu（NO 3）2 ·3H 2 O作为催化剂，而TMSCN作为非金属氰化物源，已经以高收率获得了各种含氰基的异恶唑啉。本方法提供了温和，简单和实用的氰基取代的异恶唑啉的途径，并且适用于克规模。C（sp 3）–CN和C–O键的同时构建可以一步完成。
• Trichloroisocyanuric Acid Promoted Cascade Cyclization/Trifluoromethylation of Allylic Oximes: Synthesis of Trifluoromethylated Isoxazolines
  作者：Weigang Zhang、Yingpeng Su、Ke-Hu Wang、Lili Wu、Bingbing Chang、Ya Shi、Danfeng Huang、Yulai Hu

  DOI：10.1021/acs.orglett.6b03582

  日期：2017.1.20

  Cheap and commercially available trichloroisocyanuric acid has been used to promote trifluoromethylation by using TMSCF3 as the trifluoromethyl source. The method provides a novel and efficient protocol for the construction of CF3-containing 4,5-dihydroisoxazoles from allylic oximes in good to excellent yields.

  通过使用TMCSF 3作为三氟甲基源，已经使用廉价且可商购的三氯异氰尿酸来促进三氟甲基化。该方法为从烯丙基肟构建具有CF 3的4，5-二氢异恶唑提供了新颖且有效的方案，产率高至优异。
• Oxy‐/Amino‐Difluoromethylthiolation of Alkenes: Synthesis of HCF₂S‐Containing Isoxazolines and Pyrazolines
  作者：Xin Chen、Yun‐Tao Shen、Zhi‐Wei Zhao、Yu‐Jian Hou、Bo‐Xun Sun、Tai‐Gang Fan、Ya‐Min Li

  DOI：10.1002/adsc.202200672

  日期：2022.9.20

  Oxy-/amino-difluoromethylthiolation of β,γ-unsaturated oximes/hydrazones have been developed for construction of HCF2S-containing isoxazolines and pyrazolines by employing PhSO2SCF2H as difluoromethylthiolation reagent under mild conditions. Such transformations exhibit good functional group tolerance and scalability. Possible mechanisms are proposed.

  β,γ-不饱和肟/腙的氧-/氨基-二氟甲基硫醇化已被开发用于在温和条件下使用PhSO 2 SCF 2 H 作为二氟甲基硫醇化试剂来构建含HCF 2 S 的异恶唑啉和吡唑啉。这种转换表现出良好的官能团耐受性和可扩展性。提出了可能的机制。
• Iodine(III)-Mediated Oxy-fluorination of Alkenyl Oximes: An Easy Path to Monofluoromethyl-Substituted Isoxazolines
  作者：Weidong Kong、Quanping Guo、Zhaoqing Xu、Guoqiang Wang、Xianxing Jiang、Rui Wang

  DOI：10.1021/acs.orglett.5b01646

  日期：2015.8.7

  A highly regioselective intramolecular oxy-fluorination of alkenyl oximes was achieved. This new transformation represents an efficient method for the preparation of monofluoromethyl-substituted isoxazolines. The synthetic application of the oxy-fluorination product was demonstrated by a one-step synthesis of monofluoromethyl-substituted beta-hydroxyl ketone derivatives.