(E)-methyl 5-(2-(dimethylamino)vinyl)-3-phenylisoxazole-4-carboxylate | 1610688-77-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-methyl 5-(2-(dimethylamino)vinyl)-3-phenylisoxazole-4-carboxylate
• 英文别名: methyl 5-[(E)-2-(dimethylamino)ethenyl]-3-phenyl-1,2-oxazole-4-carboxylate
• CAS: 1610688-77-1
• 化学式: C₁₅H₁₆N₂O₃
• 分子量: 272.304
• InChiKey: JXQHBAVMYRYIIX-MDZDMXLPSA-N

物化性质

• 沸点：
  476.8±45.0 °C(Predicted)
• 密度：
  1.166±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  55.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-methyl 5-(2-(dimethylamino)vinyl)-3-phenylisoxazole-4-carboxylate 在 三氟化硼-二甲醚络合物 作用下， 以 1,4-二氧六环 为溶剂， 反应 12.0h， 以80%的产率得到trimethyl 5,5',5"-(benzene-1,3,5-triyl)tris(3-phenylisoxazole-4-carboxylate)
  参考文献：
  名称：

  Self-condensation of β-(isoxazol-5-yl) enamines under treatment with acetyl chloride and acids. Synthesis of novel 1,3-diisoxazolyl-1,3-dieneamines and 1,3,5-triisoxazolyl benzenes

  摘要：

  Two directions for self-condensation of beta-(isoxazol-5-yl) enamines under treatment with either acetyl chloride or acids were found leading to new 1,3-diisoxazolyl-1,3-dieneamines and 1,3,5-triisoxazolyl benzenes. The effect of solvent, acid, temperature and the reaction time on the ratio of reaction products were investigated. Trans-E-cis configuration of prepared 1,3-diisoxazolyl-1,3-dieneamines was unambiguously confirmed by 2D NMR spectra and X-ray analysis. A new mechanism of 1,3-diisoxazolyl-1,3-dieneamines formation was proposed. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.04.015
• 作为产物：
  描述：

  5-甲基-3-苯基-4-异噁唑羧酸甲酯 、 N,N-二甲基甲酰胺二甲基缩醛 在 N-甲基咪唑 作用下， 反应 6.0h， 以70%的产率得到(E)-methyl 5-(2-(dimethylamino)vinyl)-3-phenylisoxazole-4-carboxylate
  参考文献：
  名称：

  Self-condensation of β-(isoxazol-5-yl) enamines under treatment with acetyl chloride and acids. Synthesis of novel 1,3-diisoxazolyl-1,3-dieneamines and 1,3,5-triisoxazolyl benzenes

  摘要：

  Two directions for self-condensation of beta-(isoxazol-5-yl) enamines under treatment with either acetyl chloride or acids were found leading to new 1,3-diisoxazolyl-1,3-dieneamines and 1,3,5-triisoxazolyl benzenes. The effect of solvent, acid, temperature and the reaction time on the ratio of reaction products were investigated. Trans-E-cis configuration of prepared 1,3-diisoxazolyl-1,3-dieneamines was unambiguously confirmed by 2D NMR spectra and X-ray analysis. A new mechanism of 1,3-diisoxazolyl-1,3-dieneamines formation was proposed. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.04.015

文献信息

• [3+2] Anionic Cycloaddition of Isocyanides to Acyclic Enamines and Enaminones: A New, Simple, and Convenient Method for the Synthesis of 2,4-Disubstituted Pyrroles
  作者：Ilya V. Efimov、Maria D. Matveeva、Rafael Luque、Vasiliy A. Bakulev、Leonid G. Voskressensky

  DOI：10.1002/ejoc.201901776

  日期：2020.3.8

  Herein, a new route toward 2,4‐substituted pyrroles is presented. This is a new, simple, fast, and convenient method furnishing 2,4‐substituted pyrroles based on the formal cycloaddition reaction of isocyanides with acyclic enamines or enaminones under basic conditions.

  在此，提出了一种新的制备2,4-取代吡咯的途径。这是在异氰酸酯与无环烯胺或烯胺酮在碱性条件下正式环加成反应的基础上，提供2,4-取代吡咯的一种新的，简单，快速和方便的方法。
• Combined experimental and theoretical studies of regio- and stereoselectivity in reactions of β-isoxazolyl- and β-imidazolyl enamines with nitrile oxides
  作者：Ilya V Efimov、Marsel Z Shafikov、Nikolai A Beliaev、Natalia N Volkova、Tetyana V Beryozkina、Wim Dehaen、Zhijin Fan、Viktoria V Grishko、Gert Lubec、Pavel A Slepukhin、Vasiliy A Bakulev

  DOI：10.3762/bjoc.12.233

  日期：——

  reaction of (E)-beta-imidazol-4-yl enamines with aryl and cyclohexylhydroxamoyl chlorides. Stepwise and concerted pathways for the reaction of beta-azolyl enamines with hydroxamoyl chlorides were considered and studied at the B3LYP/Def2-TZVP level of theory combined with D3BJ dispersion correction. The reactions of benzonitrile oxide with both E- and Z-imidazolyl enamines have been shown to proceed stereoselectively

  通过实验和理论方法研究了β-偶氮烯基烯胺和一氧化氮的反应。（E）-β-（4-硝基咪唑-5-基），（5-硝基咪唑-4-基）和异恶唑-5-基烯胺在室温下于二恶烷溶液中与芳基，吡啶基和环己基氢氧肟基氯平稳地区域选择性反应催化剂或碱以形成4-偶氮基乙恶唑为唯一高收率的产物。在（E）-β-咪唑-4-基烯胺与芳基和环己基羟肟基氯的反应过程中，中间体4,5-二氢异恶唑啉被分离为反式异构体。考虑并在B3LYP / Def2-TZVP理论水平结合D3BJ分散校正的基础上研究和研究了β-偶氮烯基烯胺与羟肟酰氯反应的逐步和协调的途径。已显示苯甲腈氧化物与E-和Z-咪唑基烯胺的反应分别进行立体选择性反应，分别形成反式和顺式异恶唑啉。由前者的较高稳定性驱动，E异构体优于Z异构体，显然控制了所研究的与苯甲腈小，即西里尔氧化物的环加成反应的立体选择性。基于偶氮烯基烯胺对异羟肟酸的反应性，精心设计了一种新颖，有效的无催化