1-hydroxy-4-[2-(4-iodophenyl)vinyl]-2,2,5,5-tetramethyl-3-imidazoline-3-oxide | 892397-82-9

• 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: 1-hydroxy-4-[2-(4-iodophenyl)vinyl]-2,2,5,5-tetramethyl-3-imidazoline-3-oxide
• 英文别名: 1-hydroxy-4-[2-(p-iodophenyl)vinyl]-2,2,5,5-tetramethyl-3-imidazoline-3-oxide；3-hydroxy-5-[(E)-2-(4-iodophenyl)ethenyl]-2,2,4,4-tetramethyl-1-oxidoimidazol-1-ium
• CAS: 892397-82-9
• 化学式: C₁₅H₁₉IN₂O₂
• 分子量: 386.233
• InChiKey: WXFFNXGJKXMZMU-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：
  52.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  1-羟基-2,2,4,5,5-五甲基-3-咪唑啉-3-氧化物 、 4-碘苯甲醛 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以28%的产率得到1-hydroxy-4-[2-(4-iodophenyl)vinyl]-2,2,5,5-tetramethyl-3-imidazoline-3-oxide
  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

• 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。
• Oxidative coupling of alkynes mediated by nitroxyl radicals under Sonogashira conditions and Pd-free catalytic approach to stable radicals of 3-imidazoline family with triple bonds
  作者：Sergei F. Vasilevsky、Olga L. Krivenko、Igor V. Alabugin

  DOI：10.1016/j.tetlet.2007.09.031

  日期：2007.11

  In the presence of Pd catalyst, 3-imidazoline nitroxyl radicals promote oxidative coupling (dimerization) of terminal alkynes even in the absence of Cu(II) additives. On the other hand, the Pd-free CuI–PPh3–K2CO3–DMF catalytic system leads to the efficient cross-coupling of 1-hydroxy-4-[2-(p-iodophenyl)vinyl]-2,2,5,5-tetramethyl-3-imidazoline-3-oxide with terminal aryl- and hetarylacetylenes with the

  在Pd催化剂存在下，即使不存在Cu（II）添加剂，3-咪唑啉硝基氧基也会促进末端炔烃的氧化偶联（二聚）。另一方面，无钯的CuI–PPh 3 –K 2 CO 3 –DMF催化体系导致1-羟基-4- [2-（对-碘苯基）乙烯基] -2,2的有效交叉偶联。，5,5-四甲基-3-咪唑啉-3-氧化物与末端芳基和杂芳基乙炔形成4- [2-（芳基/杂芳基乙炔基）苯基]乙烯基] -2,2,5,5-四甲基-3 -咪唑啉-3-氧化物-1-氧基的产率为70-75％。