1-(2,4-Dichlorophenyl)but-3-en-1-one | 1574316-82-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2,4-Dichlorophenyl)but-3-en-1-one
• CAS: 1574316-82-7
• 化学式: C₁₀H₈Cl₂O
• 分子量: 215.079
• InChiKey: BPAVKWLTXGBBOD-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：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(2,4-Dichlorophenyl)but-3-en-1-one 在 二(叔丁基羰基氧基)碘苯 、 盐酸羟胺 、 sodium acetate 、 氟化氢吡啶 作用下， 以 乙醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 2.0h， 生成 3-(2,4-dichlorophenyl)-5-fluoromethyl-4,5-dihydroisoxazole
  参考文献：
  名称：

  Iodine(III)-Mediated Oxy-fluorination of Alkenyl Oximes: An Easy Path to Monofluoromethyl-Substituted Isoxazolines

  摘要：

  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.

  DOI：

  10.1021/acs.orglett.5b01646
• 作为产物：
  描述：

  1-(2,4-dichlorophenyl)but-3-en-1-ol 在 Jones reagent 作用下， 以 乙醚 为溶剂， 生成 1-(2,4-Dichlorophenyl)but-3-en-1-one
  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

文献信息

• Organophotocatalytic Generation of N- and O-Centred Radicals Enables Aerobic Oxyamination and Dioxygenation of Alkenes
  作者：Xiao-Qiang Hu、Jun Chen、Jia-Rong Chen、Dong-Mei Yan、Wen-Jing Xiao

  DOI：10.1002/chem.201602597

  日期：2016.9.26

  applied for the first time to the direct conversion of N−H and O−H bonds into N‐ and O‐centred radicals, enabling a general and selective oxidative radical oxyamination and dioxygenation of various β,γ‐unsaturated hydrazones and oximes. In the reaction, O2 was employed not only as a terminal oxidant but also as the oxygen source. This protocol provided efficient access to the synthesis of various synthetically

  TEMPO和光氧化还原的催化合作策略首次应用于将N-H和O-H键直接转化为N-和O-中心的自由基，从而实现各种β，γ的一般和选择性氧化自由基的氧化和双加氧作用不饱和的和肟。在该反应中，不仅将O 2用作末端氧化剂，而且还将其用作氧源。该方案为在无金属和温和的反应条件下有效地合成各种重要的合成和生物学重要的吡唑啉，哒嗪和异恶唑啉衍生物提供了有效的途径。机理研究表明，协同有机光催化系统通过两个单电子转移（SET）过程起作用。
• Photocatalytic Generation of N-Centered Hydrazonyl Radicals:  A Strategy for Hydroamination of β,γ-Unsaturated Hydrazones
  作者：Xiao-Qiang Hu、Jia-Rong Chen、Qiang Wei、Feng-Lei Liu、Qiao-Hui Deng、André M. Beauchemin、Wen-Jing Xiao

  DOI：10.1002/anie.201406491

  日期：2014.11.3

  photocatalytic generation of N‐centered hydrazonyl radicals has been accomplished for the first time. This approach allows efficient intramolecular addition of hydrazonyl radical to terminal alkenes, thus providing hydroamination and oxyamination products in good yields. Importantly, the protocol involves deprotonation of an NH bond and photocatalytic oxidation to an N‐centered radical, thus obviating

  N中心的肼基自由基的可见光光催化生成已首次实现。该方法允许将肼基自由基有效地分子内加成至末端烯烃，从而以高收率提供氢化胺化和氧胺化产物。重要的是，该方案涉及NH键的去质子化和光催化氧化成N中心的自由基，从而避免了制备光不稳定胺前体或化学计量使用氧化剂的需要。
• Efficient Synthesis of Dihydropyrazoles by Halocyclization of β,γ-Unsaturated Hydrazones
  作者：Xiao-Qiang Hu、Jia-Rong Chen、Qiang Wei、Feng-Lei Liu、Qiao-Hui Deng、You-Quan Zou、Wen-Jing Xiao

  DOI：10.1002/ejoc.201402021

  日期：2014.5

  An efficient halocyclization of β,γ-unsaturated hydrazones with N-bromosuccinimide was developed without the addition of any additives under mild reaction conditions to provide facile access to biologically important 4,5-dihydropyrazoles. Under the optimized conditions, a variety of highly substituted 4,5-dihydropyrazole derivatives were obtained in generally good yields. Moreover, this reaction can

  在温和的反应条件下，开发了 β,γ-不饱和腙与 N-溴代琥珀酰亚胺的有效卤环化反应，无需添加任何添加剂，以方便获得生物学上重要的 4,5-二氢吡唑。在优化的条件下，以良好的收率获得了多种高度取代的 4,5-二氢吡唑衍生物。此外，该反应可以进一步应用于以一锅法合成吡唑。