2-anilino-N-(4-methylphenyl)-2-oxoethanimine oxide | 1294498-78-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-anilino-N-(4-methylphenyl)-2-oxoethanimine oxide
• CAS: 1294498-78-4
• 化学式: C₁₅H₁₄N₂O₂
• 分子量: 254.288
• InChiKey: YWTXVCRHEZPOML-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  57.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-1-(4-溴苯基)-3-(4-甲氧基苯基)丙-2-烯-1-酮 、 2-anilino-N-(4-methylphenyl)-2-oxoethanimine oxide 以 甲苯 为溶剂， 反应 4.0h， 以85%的产率得到(3RS,4SR,5SR)-4-(4-bromobenzoyl)-5-(4-methoxyphenyl)-N-phenyl-2-(4-tolyl)isoxazolidine-3-carboxamide
  参考文献：
  名称：

  Diastereoselective 1,3-dipolar cycloaddition of C,N-diaryl- and C-amido-N-arylnitrones to arylpropenones

  摘要：

  C,N-二芳基硝腙和 C-脒基-N-芳基硝腙非对映地加到取代的芳基丙烯酮中，得到具有 3RS、4SR、5SR 构型的取代的异噁唑烷。用甲基取代查尔酮第 3 位或腈酮氮原子上的芳基会降低环化反应的速率。

  DOI：

  10.1007/s11172-012-0122-6

文献信息

• The first example of 1,3-dipolar cycloaddition reactions of nitrones to vinylidenecyclopropanes
  作者：Anna G. Larina、Alexander V. Stepakov、Vitaly M. Boitsov、Alexander P. Molchanov、Vladislav V. Gurzhiy、Galina L. Starova、Anna N. Lykholay

  DOI：10.1016/j.tetlet.2011.08.116

  日期：2011.11

  The first example of 1,3-dipolar cycloaddition reactions of nitrones to vinylidenecyclopropanes is described. The nitrones react with the C1′–C2′ double bond of vinylidenecyclopropanes to give the corresponding 4-cyclopropylidene-isoxazolidines in moderate yields.

  描述了硝酮与1，1-亚乙烯基环丙烷的1，3-偶极环加成反应的第一个例子。硝酮与亚乙烯基环丙烷的C1'–C2'双键反应，以适当的收率得到相应的4-环亚丙基-异恶唑烷。
• 1,3-Dipolar cycloaddition of N-allyl substituted polycyclic derivatives of isoindole-1,3-dione with nitrones and nitrile oxides: An experimental and theoretical investigation
  作者：Mariia M. Efremova、Alexander P. Molchanov、Alexander S. Novikov、Galina L. Starova、Anna A. Muryleva、Alexander V. Slita、Vladimir V. Zarubaev

  DOI：10.1016/j.tet.2020.131104

  日期：2020.4

  Cycloaddition reactions of N-allyl substituted polycyclic derivatives of isoindole-1,3-dione with nitrones proceeds regio- and stereoselectively on the double bond of the N-allyl substituent giving substituted isoxazolidines with good yields. Regioselectivity of the cycloaddition of this dipolarophiles with nitrile oxides depends on the structure of unsaturated hydrocarbon scaffold and the reaction

  的环加成反应ñ -烯丙基取代的异吲哚-1,3-二酮的合多环衍生物与硝酮收益上的双键区域选择性和立体选择性地Ñ具有良好产率-烯丙基取代基取代给人异恶唑烷。该双亲亲物与腈氧化物的环加成反应的区域选择性取决于不饱和烃骨架的结构，该反应选择性地导致N-烯丙基取代基的内环或双键上的加合物。DFT计算用于研究选择性的原因。
• Reaction of Aldonitrones with N-Phenyl-9,10-dihydro-9,10-ethenoanthracene-11,12-dicarboximide
  作者：A. P. Molchanov、M. M. Efremova、A. V. Stepakov、T. L. Panikorovskii、R. R. Kostikov

  DOI：10.1134/s1070428018030144

  日期：2018.3

  Thermal addition of aldonitrones (C,N-diaryl- and N-aryl-C-arylcarbamoylnitrones) to the double bond of N-phenyl-9,10-dihydro-9,10-ethenoanthracene-11,12-dicarboximide yields heteropropellanes containing isoxazolidine and pyrrolidine fragments. The cycloaddition of C,N-diarylnitrones is stereoselective, and only one diastereoisomer is formed.
• Regioselective cycloaddition of C-aryl- and C-carbamoylnitrones to methyl 2-benzylidenecyclopropanecarboxylate
  作者：A. P. Molchanov、T. Q. Tran

  DOI：10.1134/s1070428012100041

  日期：2012.10

  C-Aryl- and C-carbamoylnitrones reacted with methyl 2-benzylidenecyclopropanecarboxylate in highly regioselective fashion to give the corresponding 1,3-dipolar cycloaddition products, substituted methyl 5-oxa-6-azaspiro[2.4]heptane-1-carboxylates as mixtures of two diastereoisomers.
• [3+2] Cycloaddition reactions of arylallenes with C-(N-arylcarbamoyl)- and C,C-bis(methoxycarbonyl)nitrones and subsequent rearrangements
  作者：Julia Malinina、Tung Q. Tran、Alexander V. Stepakov、Vladislav V. Gurzhiy、Galina L. Starova、Rafael R. Kostikov、Alexander P. Molchanov

  DOI：10.1016/j.tetlet.2014.04.107

  日期：2014.7