1-(2-methoxyphenyl)but-3-en-1-one oxime | 1574316-68-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(2-methoxyphenyl)but-3-en-1-one oxime
• 英文别名: N-[1-(2-methoxyphenyl)but-3-enylidene]hydroxylamine
• CAS: 1574316-68-9
• 化学式: C₁₁H₁₃NO₂
• 分子量: 191.23
• InChiKey: WFQOGZRCPIAUGA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  41.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-methoxyphenyl)but-3-en-1-one oxime 在 二(叔丁基羰基氧基)碘苯 、 氟化氢吡啶 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 2.0h， 以77%的产率得到3-(2-methoxyphenyl)-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：

  邻甲氧基苯甲醛 在 Jones reagent 、 盐酸羟胺 、 sodium acetate 、 氯化铵 、 锌 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 水 为溶剂， 生成 1-(2-methoxyphenyl)but-3-en-1-one oxime
  参考文献：
  名称：

  铜催化酮肟羧酸酯的5-内-trig环化反应：2-芳基吡咯的简便合成。

  摘要：

  已经开发了新颖且容易的铜催化的酮肟羧酸酯的5-内-trig环化反应，以合成2-芳基吡咯。该反应容许一定范围的官能团，并且是在温和条件下以高收率快速合成2-芳基吡咯的实用方法。

  DOI：

  10.1039/c4cc03129f

文献信息

• Copper-mediated oxysulfonylation of alkenyl oximes with sodium sulfinates: a facile synthesis of isoxazolines featuring a sulfone substituent
  作者：Li-Jing Wang、Manman Chen、Lin Qi、Zhidong Xu、Wei Li

  DOI：10.1039/c7cc00090a

  日期：——

  A novel and efficient Cu(OAc)2-mediated oxysulfonylation of alkenyl oximes with sodium sulfonates was developed. The reactions are easy to conduct, occur under mild conditions, and form a broad range of...

  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...
• Metal-free oxysulfonylation and aminosulfonylation of alkenyl oximes: synthesis of sulfonylated isoxazolines and cyclic nitrones
  作者：Zhong-Qi Xu、Lin-Chuang Zheng、Lin Li、Lili Duan、Yue-Ming Li

  DOI：10.1039/c8ob02879f

  日期：——

  Intramolecular oxysulfonylation of alkenyl oximes was reported. Using iodine as the catalyst, TBHP as the oxidant, and sulfonyl hydrazides as the sulfonyl radical source, a variety of sulfonylated isoxazolines were obtained in moderate to excellent yields. Cyclic nitrones could also be readily obtained under the same conditions.

  据报道，烯基肟的分子内氧磺酰化作用。以碘为催化剂，以TBHP为氧化剂，以磺酰肼为磺酰基自由基源，可以中等至极好的收率得到各种磺酰化的异恶唑啉。在相同条件下也可以容易地获得环硝酮。
• 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。
• Oxime-Mediated Oxychlorination and Oxybromination of Unactivated Olefins
  作者：Kui-Yong Dong、Hai-Tao Qin、Feng Liu、Chen Zhu

  DOI：10.1002/ejoc.201403538

  日期：2015.3

  An oxime-mediated oxychlorination and oxybromination of unactivated olefins relying on palladium catalysis has been developed. A wide range of chlorinated and brominated isoxazolines has been synthesized in moderate to good yields. To demonstrate the value of the method, the brominated isoxazoline has been further converted to other useful synthetic feedstock.

  已经开发了一种依赖钯催化的肟介导的氧氯化和氧溴化未活化烯烃。已以中等至良好的收率合成了多种氯化和溴化异恶唑啉。为了证明该方法的价值，溴化异恶唑啉已进一步转化为其他有用的合成原料。
• Room temperature iron(<scp>ii</scp>)-catalyzed radical cyclization of unsaturated oximes with hypervalent iodine reagents
  作者：Shichao Yang、Hongji Li、Pinhua Li、Jingya Yang、Lei Wang

  DOI：10.1039/c9ob02424g

  日期：——

  Here, we disclose an iron(ii)-catalyzed I-O bond cleavage of Koser's hypervalent iodine reagents (HIRs) that initiated the radical cyclization of unsaturated oximes at room temperature. This strategy is successfully applied for the construction of the isoxazoline backbone in an efficient manner. In particular, the direct introduction of a TsO group into products facilitates their late-stage transformations

  在这里，我们公开了Koser的高价碘试剂（HIR）的铁（ii）催化IO键裂解，该试剂在室温下引发了不饱和肟的自由基环化反应。该策略已成功地有效地用于异恶唑啉骨架的构建。特别地，将TsO基团直接引入产物中促进了它们在有机合成中的后期转化。