C-(N-4-methoxyphenylcarbamoyl)-N-(p-tolyl)nitrone | 1297292-57-9

• 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: C-(N-4-methoxyphenylcarbamoyl)-N-(p-tolyl)nitrone
• 英文别名: c-(N-4-methoxyphenylcarbamoyl)-N-(p-tolyl)-nitrone；2-(4-methoxyanilino)-N-(4-methylphenyl)-2-oxoethanimine oxide
• CAS: 1297292-57-9
• 化学式: C₁₆H₁₆N₂O₃
• 分子量: 284.315
• InChiKey: WAOSOHVQEUZSBY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  67.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  dimethyl 2-benzylidenecyclopropane-1,1-dicarboxylate 、 C-(N-4-methoxyphenylcarbamoyl)-N-(p-tolyl)nitrone 在 溶剂黄146 、 锌 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 4.0h， 生成 methyl 5-[(4-methoxyphenylcarbamoyl)-(4-tolylamino)methyl]-2-oxo-4-phenyl-3-oxabicyclo[3.1.0]hexane-1-carboxylate
  参考文献：
  名称：

  An efficient and stereoselective cycloaddition of C-aryl and C-amido nitrones to dimethyl 2-benzylidenecyclopropane-1,1-dicarboxylate

  摘要：

  1,3-Dipolar cycloalditions of dimethyl 2-benzylidenecyclopropane-1,1-dicarboxylate and a number of C-aryl or C-amido nitrones proceed with high efficiency and selectivity with the formation of only one isomeric spiral[cyclopropane-1,4-isoxazolidine] cycloadduct. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.02.013
• 作为产物：
  描述：

  对硝基甲苯 、 1-[(4-Methoxy-phenylcarbamoyl)-methyl]-pyridinium; chloride 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 以79%的产率得到C-(N-4-methoxyphenylcarbamoyl)-N-(p-tolyl)nitrone
  参考文献：
  名称：

  Regio- and stereoselectivity of cycloaddition of C-amidonitrones to esters of methylenecyclopropanedicarboxylic acids

  摘要：

  C-Amidonitrones add regio- and stereoselectively to esters of 3-methylenecyclopropane-1,2-dicarboxylic, 2-(diphenylmethylene)cyclopropane-1,1-dicarboxylic, and 2-(1-phenylethylidene)cyclopropane-1,1-dicarboxylic acids to form a single diastereomer of 4-spirocyclopropaneisoxazolidines.

  DOI：

  10.1134/s1070428011020187

文献信息

• Regio- and diastereoselectivity of the cycloaddition of aldonitrones with benzylidenecyclopropane: An experimental and theoretical study
  作者：Ekaterina V. Sirotkina、Mariia M. Efremova、Alexander S. Novikov、Vladimir V. Zarubaev、Iana R. Orshanskaya、Galina L. Starova、Rafael R. Kostikov、Alexander P. Molchanov

  DOI：10.1016/j.tet.2017.04.014

  日期：2017.5

  1,3-Dipolar cycloaddition of benzylidenecyclopropane with various aldonitrones proceeds regioselectively giving good yields of 4-spirocyclopropane isoxazolidines. In the case of aldonitrones, bearing carbamoyl- or aryl-groups on the carbon atom, only the cis-isomer is formed. The compounds synthesized were tested for their virus-inhibiting activity.

  亚苄基环丙烷与各种醛基的1，3-偶极环加成反应可以区域选择性地产生，从而得到4-螺环丙烷异恶唑烷的良好产率。对于在碳原子上带有氨基甲酰基或芳基的醛基亚硝基，仅形成顺式异构体。测试合成的化合物的病毒抑制活性。
• Diastereoselective 1,3-dipolar cycloaddition of C,N-diaryl- and C-amido-N-arylnitrones to arylpropenones
  作者：A. P. Molchanov、T. Q. Tran、R. R. Kostikov

  DOI：10.1007/s11172-012-0122-6

  日期：2012.4

  C,N-diarylnitrones and C-amido-N-arylnitrones add diastereoselectively to the substituted arylpropenones to give the substituted isoxazolidine possessing 3RS,4SR,5SR configuration. Replacement of the aryl groups either in the position 3 of chalcone or at the nitrogen atom of nitrone by the methyl group decreased the rate of cycloaddition.

  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。
• 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.