1,2,2,5,5-pentamethyl-3-imidazoline 3-oxide | 97481-71-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: 1,2,2,5,5-pentamethyl-3-imidazoline 3-oxide
• 英文别名: 1H-imidazole, 2,5-dihydro-1,2,2,5,5-pentamethyl-, 3-oxide；2,2,3,4,4-pentamethyl-1-oxidoimidazol-1-ium
• CAS: 97481-71-5
• 化学式: C₈H₁₆N₂O
• 分子量: 156.228
• InChiKey: UNPSXBKCCZEIRN-UHFFFAOYSA-N

物化性质

• 沸点：
  267.3±33.0 °C(Predicted)
• 密度：
  0.98±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  32
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,2,2,5,5-pentamethyl-3-imidazoline 3-oxide 在 仲丁基锂 、 对甲苯磺酰氯 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.33h， 以90%的产率得到5-Chloro-2,2,3,4,4-pentamethyl-1-oxidoimidazol-1-ium
  参考文献：
  名称：

  A route to the synthesis of previously unknown α-heteroatom substituted nitrones

  摘要：

  alpha-Heteroatom substituted nitrones have been synthesized for the first time by the reaction of alpha-lithiated cyclic aldonitrone 1,2,2.5,5-pentamethyl-3-imidazoline 3-oxide with HgCl2, (CH3)(3)SiCl, (C2H5)(3)GeCl, (n-C4H9)(3)SnBr and Ph2P(O)Cl. alpha-Chloronitrone was prepared for the first time by direct chlorination of alpha-lithiated aldonitrone using TsCl. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00279-4
• 作为产物：
  描述：

  4-carboxy-1,2,2,5,5-pentamethyl-3-imidazoline 3-oxide 以 正庚烷 为溶剂， 以83%的产率得到1,2,2,5,5-pentamethyl-3-imidazoline 3-oxide
  参考文献：
  名称：

  环状硝酮的13 C NMR光谱。2. 1-和4-取代的2,2,5,5-四甲基-3-咪唑啉3-氧化物

  摘要：

  DOI：

  10.1007/bf00504212

文献信息

• α-Organoelement Nitrones:  Synthesis, Properties, and IR and¹³C NMR Spectral and X-ray Structural Characterization
  作者：Maxim A. Voinov、Tikhon G. Shevelev、Tatyana V. Rybalova、Yury V. Gatilov、Natalie V. Pervukhina、Aleksei B. Burdukov、Igor A. Grigor'ev

  DOI：10.1021/om060883o

  日期：2007.3.1

  the α-lithiated cyclic aldonitrones of 3-imidazoline 3-oxide, pyrroline 1-oxide, 2H-imidazole 1-oxide, and 3,4-dihydroisoquinoline 2-oxide series with electrophilic reagents such as HgCl2, (CH3)3SiCl, (C2H5)3GeCl, (n-C4H9)3SnBr, Ph2P(O)Cl, Ph2PCl, PhSSPh, PhSeSePh, TsCl, and TsF. Aldonitrones of the 3-imidazoline 3-oxide and pyrroline 1-oxide series were shown to readily afford the products of the li

  通过3-咪唑啉3-氧化物，吡咯啉1-氧化物，2 H-咪唑1-氧化物和3,4-二氢异喹啉的α-锂化的环状醛酮的反应，首次合成了α-有机元素取代的硝基酮。与诸如HgCl 2，（CH 3）3 SiCl，（C 2 H 5）3 GeCl，（n -C 4 H 9）3 SnBr，Ph 2 P（O）Cl，Ph 2等亲电试剂的2氧化物系列PCl，PhSSPh，PhSeSePh，TsCl和TsF。显示3-氧化3-咪唑啉和1-氧化吡咯啉的醛酮很容易提供锂化-亲电取代反应的产物。相反，2 H-咪唑一氧化物和3，4-二氢异喹啉2-氧化物系列的醛亚硝基仅与无卤素的亲电试剂平滑反应。发现即使在分子中存在动力学上更酸性的亚甲基和氨基时，醛亚硝基也可被锂化并选择性地与亲电试剂反应。讨论了合成化合物的IR和13 C NMR光谱的特征。通过X射线衍射研究对选定的α-有机元素硝酮进行表征。
• Regio- and stereoselectivity of 1,3-dipolar cycloaddition of cyclic aldonitrones of the 3-imidazoline 3-oxide series to monosubstituted alkenes
  作者：T. A. Berezina、V. A. Reznikov、V. I. Mamatyuk、P. A. Butakov、Yu. V. Gatilov、I. Yu. Bagryanskaya、L. B. Volodarsky

  DOI：10.1007/bf00717351

  日期：1994.5

  Regio- and stereoselectivity of 1,3-dipolar cycloaddition of cyclic aldonitrones of the 3-imidazoline 3-oxide series mainly depends on the type of the substituent in the dipolarophile. The configuration of the main cycloadduct has been determined, and a method has been suggested to establish the stereochemistry of the cycloaddition products by1H NMR spectroscopy. An increase in electron-acceptor properties

  3-咪唑啉 3-氧化物系列的环状醛硝酮的 1,3-偶极环加成反应的区域选择性和立体选择性主要取决于亲偶极试剂中取代基的类型。确定了主要环加合物的构型，并提出了一种通过 1 H NMR 光谱建立环加成产物立体化学的方法。烯烃分子中取代基的电子受体性质的增加导致环加成的区域和立体选择性的降低。
• Dipole-stabilized carbanions in series of cyclic aldonitrones: Part 4.13C,14N and7Li NMR spectra of dipole-stabilized organolithiums derived from a cyclic aldonitrone
  作者：Maxim A. Voinov、Georgy E. Salnikov、Alexander M. Genaev、Victor I. Mamatyuk、Makhmut M. Shakirov、Igor A. Grigor'ev

  DOI：10.1002/mrc.906

  日期：2001.11

  13C, 14N and 7Li NMR spectra of a lithiation product of the cyclic aldonitrone 1,2,2,5,5‐pentamethyl‐3‐imidazoline 3‐oxide were obtained. The 13C NMR spectrum of the lithiated particle exhibits the resonances of the C‐4 and C‐5 atoms (δ213 ppm and 73 ppm, respectively) shifted to high frequency relative to the signals of the corresponding nuclei of the starting nitrone (δC‐4 132 ppm and δC‐5 60 ppm)

  获得了环状醛硝酮 1,2,2,5,5-五甲基-3-咪唑啉 3-氧化物的锂化产物的 13C、14N 和 7Li NMR 谱。锂化颗粒的 13C NMR 谱显示 C-4 和 C-5 原子（分别为 δ213 ppm 和 73 ppm）的共振相对于起始硝酮（δC-4 132 ppm 和 δC-5 60 ppm）。与起始硝酮的 -74 ppm 相比，颗粒的 14N NMR 光谱显示了 N-3 原子 (-115 ppm) 在较低频率下的共振。计算出的化学位移变化与实验观察到的非常一致。讨论了锂化粒子的电子结构。版权所有 © 2001 John Wiley & Sons, Ltd.
• Reactions of aldonitrones (3-imidazoline-3-oxides) with isothiocyanates
  作者：M. A. Voinov、V. V. Martin、L. B. Volodarskii

  DOI：10.1007/bf00863378

  日期：1992.11

  Cycloaddition of aldonitrones (derivatives of 3-imidazoline-3-oxide) to isothiocyanates depends on the N(1) substituent. Electron donating substituents facilitate cycloaddition to the C=N bond, whereas electron acceptors activate the C=S bond. Hydrolysis of adducts on the C=N bond followed by oxidation gives nitroxide radicals which are pH-sensitive spin probes.
• Dipole-Stabilized Carbanions in Series of Cyclic Aldonitrones. Part 2: Reactions of the Metalated Aldonitrones—Derivatives of 3-Imidazoline 3-Oxide and 2H-Imidazole 1-Oxide with Aldehydes and Ketones
  作者：Maxim A. Voinov、Igor A. Grigor'ev、Leonid B. Volodarsky

  DOI：10.1016/s0040-4020(00)00321-5

  日期：2000.6

  Metalated aldonitrones of 3-imidazoline 3-oxide and 2H-imidazole 1-oxide series react with a wide variety of aldehydes and ketones leading to the unknown alpha-hydroxymethyl nitrones. Reaction of 2,2-dimethyl-4-phenyl-2H-imidazole 1-oxide with allylacetone spontaneously lead to tricyclic 3,3,8-trimethyl-1-phenyl-5a,6,7,8-tetrahydro-3H,5H-4-oxa-2,3a-diaza-cydopenta[c]pentalen-8-ol. The hydroxy group of (1,2,2,5,5-pentamethyl-2,5-dihydro-1H-imidazol-3-oxide-4-yl)phenylmethanol is substituted with piperidine to give, after further transformations, (1,2,2,5,5-pentamethyl-2,5-dihydro-1H-imidazol-4-yl)phenylmethanone. (C) 2000 Elsevier Science Ltd. All rights reserved.

表征谱图