(E)-1,2-diphenyl-but-3-en-1-one oxime | 1221447-22-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E)-1,2-diphenyl-but-3-en-1-one oxime
• CAS: 1221447-22-8
• 化学式: C₁₆H₁₅NO
• 分子量: 237.301
• InChiKey: HUECGNDNYTUYGI-MSUUIHNZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.83
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  (E)-1,2-diphenyl-but-3-en-1-one oxime 在 1,10-菲罗啉 、 palladium diacetate 、 溶剂黄146 、 potassium carbonate 作用下， 以 水 、 1,2-二氯乙烷 、 甲醇 为溶剂， 20.0~40.0 ℃ 、101.33 kPa 条件下， 反应 1.0h， 以36%的产率得到trans-3,4-diphenyl-2-isoxazoline-5-methanol
  参考文献：
  名称：

  Palladium-Catalyzed Oxime Assisted Intramolecular Dioxygenation of Alkenes with 1 atm of Air as the Sole Oxidant

  摘要：

  This paper describes a palladium-catalyzed oxime assisted intramolecular dioxygenation of alkenes by using 1 atm of air as the sole oxidant under extremely mild conditions, which demonstrated the feasibility of incorporating atmospheric oxygen into synthetically useful products under 1 atm of air at room temperature.

  DOI：

  10.1021/ja100716x
• 作为产物：
  描述：

  1,2-diphenylbut-3-en-1-one 在 吡啶 、 盐酸羟胺 作用下， 反应 1.0h， 生成 (E)-1,2-diphenyl-but-3-en-1-one oxime 、 (Z)-1,2-diphenyl-but-3-en-1-one oxime
  参考文献：
  名称：

  Palladium-Catalyzed Oxime Assisted Intramolecular Dioxygenation of Alkenes with 1 atm of Air as the Sole Oxidant

  摘要：

  This paper describes a palladium-catalyzed oxime assisted intramolecular dioxygenation of alkenes by using 1 atm of air as the sole oxidant under extremely mild conditions, which demonstrated the feasibility of incorporating atmospheric oxygen into synthetically useful products under 1 atm of air at room temperature.

  DOI：

  10.1021/ja100716x

文献信息

• Cobalt-catalyzed aerobic oxidative cyclization of β,γ-unsaturated oximes
  作者：Weifei Li、Pingjing Jia、Bing Han、Dianjun Li、Wei Yu

  DOI：10.1016/j.tet.2013.02.032

  日期：2013.4

  Cobalt complex Co(nmp)2 can efficiently catalyze the aerobic oxidative 5-exo cyclization of β,γ-unsaturated oximes to afford isoxazolines. The key cyclization step involves the generation of carbon-centred radicals. The products are largely dependent on the reaction conditions. The oxidative termination products 2 were produced predominantly when the reaction was carried out in i-PrOH, whereas the

  钴配合物Co（nmp）2可以有效催化β，γ-不饱和肟的有氧氧化5-外切环化反应，得到异恶唑啉。关键的环化步骤涉及碳中心自由基的产生。产物在很大程度上取决于反应条件。当在i -PrOH中进行反应时，主要产生氧化终止产物2，而在环己-1,4-二烯存在下，在甲苯中选择性地获得还原终止产物3。
• Copper-Catalyzed Oxyazidation of Unactivated Alkenes: A Facile Synthesis of Isoxazolines Featuring an Azido Substituent
  作者：Liping Zhu、Hongmei Yu、Zhaoqing Xu、Xianxing Jiang、Li Lin、Rui Wang

  DOI：10.1021/ol403687k

  日期：2014.3.21

  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.