4-[2-(4-iodophenyl)vinyl]-2,2,5,5-tetramethyl-3-imidazoline-3-oxide-1-oxyl | 892397-83-0

• 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: 4-[2-(4-iodophenyl)vinyl]-2,2,5,5-tetramethyl-3-imidazoline-3-oxide-1-oxyl
• 英文别名: 4-[2-(4-iodophenyl)vinyl]-2,2,5,5-tetramethyl-3-imidazolin-1-oxyl 3-oxide
• CAS: 892397-83-0
• 化学式: C₁₅H₁₈IN₂O₂
• 分子量: 385.225
• InChiKey: JKHYARXLMLSDQS-JXMROGBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-bromo-4-ethynylbenzene,copper(1+) 、 4-[2-(4-iodophenyl)vinyl]-2,2,5,5-tetramethyl-3-imidazoline-3-oxide-1-oxyl 在 吡啶 作用下， 反应 5.0h， 以91%的产率得到2,2,5,5-tetramethyl-4-{2-[4-(4-bromophenylethynyl)phenyl]vinyl}-3-imidazoline-3-oxide-1-oxyl
  参考文献：
  名称：

  3-咪唑啉系列的硝基氧基与末端炔的交叉偶联的合成和机理方面

  摘要：

  通过3-咪唑基卤化物与末端炔烃或它们的铜盐的交叉偶联反应，开发了用于新型3-咪唑基-3-氧化物-1-氧基的炔属衍生物的实用合成方法，包括双自由基。硝氧基官能团作为内部氧化剂的存在导致交叉偶联产物的形成与氧化均偶联产物之间的竞争。通过包括催化剂的性质，卤化物的反应性和反应条件在内的多种因素的组合，可以使竞争中的平衡向交叉偶联产物转移。

  DOI：

  10.1016/j.tet.2008.06.088
• 作为产物：
  描述：

  1-hydroxy-4-[2-(4-iodophenyl)vinyl]-2,2,5,5-tetramethyl-3-imidazoline-3-oxide 在 sodium periodate 作用下， 以 氯仿 、 水 为溶剂， 反应 2.5h， 以72%的产率得到4-[2-(4-iodophenyl)vinyl]-2,2,5,5-tetramethyl-3-imidazoline-3-oxide-1-oxyl
  参考文献：
  名称：

  Stable nitroxyl radicals with triple bonds: 4-acetylenyl-3-imidazoline-3-oxide-1-oxyls

  摘要：

  Cross-coupling reaction of 1-hydroxy-2,2,5,5-tetramethyl-4-[2-(p-iodophenyl)vinyl]1-3-imidazoline-3-oxide with copper(l) salts of 1-aryl(hetaryl)alkynes leads to the corresponding 2,2,5,5-tetramethyl-4-[2-(p-aryl(hetaryl)ethynylphenyl)vinyl]-3-imidazoline-3-oxide-1-oxyls in high yields. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.02.036

文献信息

• Synthesis and properties of the first representatives of terminal acetylenes in 3-imidazoline-1-oxyl 3-oxide series
  作者：O. L. Krivenko、S. F. Vasilevskii

  DOI：10.1007/s11172-007-0333-4

  日期：2007.10

  Method for the synthesis of m-and p-isomers of 4-[2-(ethynylphenyl)vinyl]-2,2,5,5-tetramethyl-3-imidazoline-1-oxyl 3-oxides by the cross-coupling of 4-[2-(3-iodophenyl)vinyl]-and 4-[2-(4-iodophenyl)vinyl]-2,2,5,5-tetramethyl-3-imidazoline-1-oxyl 3-oxides with (trimethylsilyl)acetylene followed by desilylation was elaborated. The reactions at the CH-fragment of the ethynyl group were performed. The

  通过 4 的交叉偶联合成 4-[2-(ethynylphenyl)vinyl]-2,2,5,5-tetramethyl-3-imidazoline-1-oxyl 3-oxides 的 m-和 p-异构体的方法-[2-(3-iodophenyl)vinyl]-和 4-[2-(4-iodophenyl)vinyl]-2,2,5,5-tetramethyl-3-imidazoline-1-oxyl 3-oxides with (trimethylsilyl)乙炔然后脱甲硅烷被详细说明。在乙炔基的CH​​-片段处进行反应。曼尼希反应会随着自旋标记的丢失而进行，而氧化同源偶联会随着其保留而进行。
• First acetylenic derivatives of stable 3-imidazoline nitroxides
  作者：Sergei F. Vasilevsky、Svetlana V. Klyatskaya、Olga L. Korovnikova、Dmitri V. Stass、Svetlana A. Amitina、Igor A. Grigir’ev、José Elguero

  DOI：10.1016/j.tetlet.2004.08.063

  日期：2004.10

  The Stephens-Castro reaction of copper(I) salts of 1-aryl(hetaryl)alkynes with 2,2,5,5-tetramethyl-4-[2-(4-iodophenyl)-vinyl]imidazoline-3-oxide- 1-ol proved to be a general method for the preparation of 2,2,5,5-tetramethyl-4-[2-)-aryl(hetaryl)ethynylphenyl)]vinyl-3-imidazoline- 3 -oxide-1-oxyles. (C) 2004 Elsevier Ltd. All rights reserved.
• Stable nitroxyl radicals with triple bonds: 4-acetylenyl-3-imidazoline-3-oxide-1-oxyls
  作者：Sergei F. Vasilevsky、Svetlana V. Klyatskaya、Olga L. Korovnikova、Svetlana A. Amitina、Dmitri V. Stass、Igor A. Grigor'ev、José Elguero

  DOI：10.1016/j.tet.2006.02.036

  日期：2006.5

  Cross-coupling reaction of 1-hydroxy-2,2,5,5-tetramethyl-4-[2-(p-iodophenyl)vinyl]1-3-imidazoline-3-oxide with copper(l) salts of 1-aryl(hetaryl)alkynes leads to the corresponding 2,2,5,5-tetramethyl-4-[2-(p-aryl(hetaryl)ethynylphenyl)vinyl]-3-imidazoline-3-oxide-1-oxyls in high yields. (c) 2006 Elsevier Ltd. All rights reserved.
• Synthetic and mechanistic aspects of cross-coupling of nitroxyl radicals of 3-imidazoline series with terminal alkynes
  作者：Sergei F. Vasilevsky、Olga L. Krivenko、Vitalii R. Gorelik、Igor V. Alabugin

  DOI：10.1016/j.tet.2008.06.088

  日期：2008.9

  Practical synthetic approaches to the new class of acetylenic derivatives of 3-imidazolyl-3-oxide-1-oxyls, including biradicals, were developed through cross-coupling reactions of 3-imidazolyl halides with either terminal alkynes or their copper salts. The presence of nitroxyl functional group as an internal oxidant leads to a competition between the formation of cross-coupling products and the products

  通过3-咪唑基卤化物与末端炔烃或它们的铜盐的交叉偶联反应，开发了用于新型3-咪唑基-3-氧化物-1-氧基的炔属衍生物的实用合成方法，包括双自由基。硝氧基官能团作为内部氧化剂的存在导致交叉偶联产物的形成与氧化均偶联产物之间的竞争。通过包括催化剂的性质，卤化物的反应性和反应条件在内的多种因素的组合，可以使竞争中的平衡向交叉偶联产物转移。