N-叔丁基-alpha-(2,4,6-三甲氧基-苯基)硝酮 | 57833-64-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: N-叔丁基-alpha-(2,4,6-三甲氧基-苯基)硝酮
• 英文名称: N-tert-butyl-α-(2,4,6-trimethoxyphenyl)nitrone
• 英文别名: α-2,4,6-(trimethoxyphenyl)-N-tert-butylnitrone；(Z)-N-2,4,6-Trimethoxybenzylidene-t-butanamine oxide；2,4,6-Trimethoxy-phenyl-N-t-butylnitron；N-tert-Butyl-alpha-(2,4,6-trimethoxy-phenyl)nitrone,99；N-tert-butyl-1-(2,4,6-trimethoxyphenyl)methanimine oxide
• CAS: 57833-64-4
• 化学式: C₁₄H₂₁NO₄
• 分子量: 267.325
• InChiKey: PHKZCVKPGLECTC-DHDCSXOGSA-N

物化性质

• 熔点：
  98-100 °C(lit.)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  56.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-叔丁基-alpha-(2,4,6-三甲氧基-苯基)硝酮 生成 2-methyl-N-oxidopropan-2-amine
  参考文献：
  名称：

  REHOREK, D.;DU, BOSE, C. M.;JANZEN, E. G., Z. CHEM., 1984, 24, N 5, 188

  摘要：

  DOI：
• 作为产物：
  描述：

  2-甲基-2-硝基丙烷 、 2,4,6-三甲氧基苯甲醛 在 溶剂黄146 、 锌 作用下， 以 乙醇 为溶剂， 生成 N-叔丁基-alpha-(2,4,6-三甲氧基-苯基)硝酮
  参考文献：
  名称：

  氟代链烷酸酯和氟化异恶唑烷酮的立体选择性合成：控制亚硝基双反应性的N-取代基

  摘要：

  α-氟链烯酸酯和4-氟-5-异恶唑烷酮因其潜在的生物学应用而备受关注。现在，我们通过硝酮与α-氟代-α-溴乙酸酯之间的反应证明（E）-α-氟代链烯酸酯和4-氟代-5-异恶唑烷酮的合成。通过改变硝酮中的N-取代基，可以实现高化学选择性和立体选择性，分别获得（E）-α-氟代链烯酸酯和4-氟-5-异恶唑烷酮。已经进行了实验和计算研究以阐明反应机理。线性自由能关系研究进一步表明，N取代基效应主要是电子起源的。

  DOI：

  10.1002/chem.201303509

文献信息

• A highly stereoselective synthesis of α,β-unsaturated oxazolines
  作者：Vito Capriati、Leonardo Degennaro、Saverio Florio、Renzo Luisi

  DOI：10.1016/s0040-4039(01)02025-1

  日期：2001.12

  Lithiated 2,4,4-trimethyl-2-oxazoline 2a and 2-chloromethyl-4.4-dimethyl-2-oxazoline 2b react smoothly with a number of nitrones 3 to produce alpha,beta -unsaturated oxazolines 6 and 7 highly stereoselectively. (C) 2001 Elsevier Science Ltd. All rights reserved.
• On the Addition of Lithiated 2-Alkyl- and 2-(Chloroalkyl)-4,5-dihydro-1,3-oxazoles to Nitrones − A Mechanistic Investigation
  作者：Vito Capriati、Leonardo Degennaro、Saverio Florio、Renzo Luisi

  DOI：10.1002/1099-0690(200209)2002:17<2961::aid-ejoc2961>3.0.co;2-f

  日期：2002.9

  The addition of 2-(lithioalkyl)-4,5-dihydro-1,3-oxazoles 2a-c and 2-[chloro(lithio)alkyl]-4,5-dihydro-1,3-oxazoles 2d,e to nitrones 3 has been studied. While lithiated 2-methyl-4,5-dihydro-1,3-oxazole 2a adds stereoselectively to nitrones 3, resulting after long reaction times (3 h) in the formation of 2-[(E)-alkenyl]-4,5-dihydro-1,3-oxazoles 8a-h, lithiated 2(chloromethyl)-4,5-dihydro-1,3-oxazole 2e affords 2-[(Z)-alkenyl]-4,5-dihydro-1,3-oxazoles 26a-d and 26f-h. alpha-Lithiated 2-ethyl-4,5-dihydro-1,3-oxazole 2b adds to 3a to give the 1,6-dioxa-2,9-diazaspiro[4.4]nonane 9 and 2-alkenyl-4,5-dihydro-1,3-oxazole 14 after treatment with oxalic acid. Quenching after short reaction times shows that the conversions of 2a to 8 and of 2b to 14 go through spirocyclic compounds 7 and 9, while the reaction between 2e and 3a, quenched even at short reaction times, gives a mixture of the 1,6-dioxa-2,9diazaspiro[4.4]nonanes 21-H and 22-H and the 2-(1,2-oxazetidin-4-yl)-4,5-dihydro-1,3-oxazoles 25a and 27a. The addition of 2c to 3a furnishes the 1,6-dioxa-2,9-diazaspiro[4.4]nonane 15 and then isoxazolidin-5-one 16 upon hydrolysis with oxalic acid. The addition of 2d to 3a gives the 1,6-dioxa-2,9-diazaspiro[4.4]nonanes 17b and 18b after short reaction times and the 2-(1,2-oxazetidin-4-yl)-4,5-dihydro-1,3-oxazole 19 after long reaction times. (C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.
• Recognition ability of cyclodextrin for alkyl groups in nitroxides as studied by electron spin resonance
  作者：Yashige Kotake、Edward G. Janzen

  DOI：10.1021/ja00196a018

  日期：1989.7
• Stereoselective Synthesis of Fluoroalkenoates and Fluorinated Isoxazolidinones: N-Substituents Governing the Dual Reactivity of Nitrones
  作者：G. K. Surya Prakash、Zhe Zhang、Fang Wang、Martin Rahm、Chuanfa Ni、Marc Iuliucci、Ralf Haiges、George A. Olah

  DOI：10.1002/chem.201303509

  日期：2014.1.13

  α‐Fluoroalkenoates and 4‐fluoro‐5‐isoxazolidinones are of vast interest due to their potential biological applications. We now demonstrate the syntheses of (E)‐α‐fluoroalkenoates and 4‐fluoro‐5‐isoxazolidinones by the reactions between nitrones and α‐fluoro‐α‐bromoacetate. By altering N‐substituents in nitrones, (E)‐α‐fluoroalkenoates and 4‐fluoro‐5‐isoxazolidinones can be achieved, respectively, with

  α-氟链烯酸酯和4-氟-5-异恶唑烷酮因其潜在的生物学应用而备受关注。现在，我们通过硝酮与α-氟代-α-溴乙酸酯之间的反应证明（E）-α-氟代链烯酸酯和4-氟代-5-异恶唑烷酮的合成。通过改变硝酮中的N-取代基，可以实现高化学选择性和立体选择性，分别获得（E）-α-氟代链烯酸酯和4-氟-5-异恶唑烷酮。已经进行了实验和计算研究以阐明反应机理。线性自由能关系研究进一步表明，N取代基效应主要是电子起源的。
• REHOREK, D.;DU, BOSE, C. M.;JANZEN, E. G., Z. CHEM., 1984, 24, N 5, 188
  作者：REHOREK, D.、DU, BOSE, C. M.、JANZEN, E. G.

  DOI：——

  日期：——