α-(3,4-methylenedioxyphenyl)-N-tert-butylnitrone | 115171-13-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: α-(3,4-methylenedioxyphenyl)-N-tert-butylnitrone
• 英文别名: 1-(1,3-benzodioxol-5-yl)-N-tert-butylmethanimine oxide
• CAS: 115171-13-6
• 化学式: C₁₂H₁₅NO₃
• 分子量: 221.256
• InChiKey: JMJDVDWVBUEBBW-QPEQYQDCSA-N

物化性质

• 熔点：
  87 °C
• 沸点：
  345.9±52.0 °C(Predicted)
• 密度：
  1.163±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  47.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-chloromethyl-4,4-dimethyl-4,5-dihydro-1,3-oxazole 、 α-(3,4-methylenedioxyphenyl)-N-tert-butylnitrone 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以38%的产率得到2-[(Z)-2-(1,3-benzodioxol-5-yl)vinyl]-4,4-dimethyl-4,5-dihydro-1,3-oxazole
  参考文献：
  名称：

  On the Addition of Lithiated 2-Alkyl- and 2-(Chloroalkyl)-4,5-dihydro-1,3-oxazoles to Nitrones − A Mechanistic Investigation

  摘要：

  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.

  DOI：

  10.1002/1099-0690(200209)2002:17<2961::aid-ejoc2961>3.0.co;2-f
• 作为产物：
  描述：

  胡椒醛 、 N-叔丁基羟胺盐酸盐 在 sodium sulfate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以51%的产率得到α-(3,4-methylenedioxyphenyl)-N-tert-butylnitrone
  参考文献：
  名称：

  α-Phenyl-N-tert-butyl nitrone (PBN) derivatives: Synthesis and protective action against microvascular damages induced by ischemia/reperfusion

  摘要：

  Nitrones 4-7, structurally related to PBN (1), were prepared by reaction of the corresponding aromatic aldehydes with N-tert-butyl hydroxylamine. The protective effects of these nitrones against microvascular damages in ischemia/reperfusion in the 'hamster cheek pouch' assay were studied and 1, as well as 4a, 4b, and 7 (derived from piperonal, O-benzyl vanillin, and furfural, respectively), showed to be more active than shark cartilage or a-tocopherol. No correlation was found between the protective effect of these nitrones and their log P (partition coefficient) or their capacity to trap OH and CH3 radicals. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.02.033

文献信息

• Iridium(III)-Catalyzed C–H Amidation of Nitrones with Dioxazolones
  作者：Xia Mi、Weisheng Feng、Chao Pi、Xiuling Cui

  DOI：10.1021/acs.joc.9b00300

  日期：2019.5.3

  efficiently achieved through Ir(III)-catalyzed direct C–H amidation of nitrones with good to excellent yields and tolerance of broad functional groups. This reaction smoothly proceeded at room temperature in the absence of acid or base in a short reaction time. Carbon dioxide was generated as the sole byproduct, thus providing an environmentally benign amidation process. The title products could be efficiently

  通过Ir（III）催化的硝基甲烷的直接C–H酰胺化反应，可以高效地获得各种酰胺化的硝酮，并具有良好至优异的收率和宽泛的官能团耐受性。该反应在短时间内在室温下在不存在酸或碱的条件下平稳地进行。产生二氧化碳作为唯一的副产物，因此提供了对环境无害的酰胺化过程。标题产物可以有效地转化为取代的苯并异恶唑啉。
• Alpha-aryl-N-alkylnitrones and pharmaceutical compositions containing the same
  申请人：Kelleher A. Judith

  公开号：US20050124691A1

  公开（公告）日：2005-06-09

  Disclosed are novel α-aryl-N-alkylnitrone compounds and pharmaceutical compositions containing such compounds. The disclosed compositions are useful as therapeutics for preventing and/or treating neurodegenerative, autoimmune and inflammatory conditions in mammals and as analytical reagents for detecting free radicals.

  本发明涉及一种新型的α-芳基-N-烷基亚硝基化合物和含有这种化合物的药物组合物。所述组合物可用作治疗哺乳动物神经退行性、自身免疫和炎症疾病的治疗剂，并可用作检测自由基的分析试剂。
• 10.1021/acs.joc.4c00512
  作者：Xing, Jian、Tang, Hong-Yu、Chen, Jing-Lin、Huang, Zheng、Liang, Jun-Jie、Quan, Yao-Sheng、Mao, Jian-Gang

  DOI：10.1021/acs.joc.4c00512

  日期：——

  methodology for the synthesis of nitrones via palladium-catalyzed redox cross-coupling of nitro compounds and alcohols is established. The protocol is a mild, convenient, ligand-free, and scalable synthesis method that can be compatible with various nitro compounds and alcohols. Nitrone is a significant multifunctional platform synthon which can be synthesized directly and efficiently via this tactic from

  建立了一种通过硝基化合物和醇的钯催化氧化还原交叉偶联合成硝酮的新方法。该方案是一种温和、方便、无配体、可扩展的合成方法，可以与各种硝基化合物和醇兼容。硝酮是一种重要的多功能平台合成子，可以通过这种策略从市售且廉价的原材料直接有效地合成。
• α-Phenyl-N-tert-butyl nitrone (PBN) derivatives: Synthesis and protective action against microvascular damages induced by ischemia/reperfusion
  作者：Sothea Kim、Guilherme V.M. de A. Vilela、Jalloul Bouajila、Ayres G. Dias、Fatima Z.G.A. Cyrino、Eliete Bouskela、Paulo R.R. Costa、Françoise Nepveu

  DOI：10.1016/j.bmc.2007.02.033

  日期：2007.5

  Nitrones 4-7, structurally related to PBN (1), were prepared by reaction of the corresponding aromatic aldehydes with N-tert-butyl hydroxylamine. The protective effects of these nitrones against microvascular damages in ischemia/reperfusion in the 'hamster cheek pouch' assay were studied and 1, as well as 4a, 4b, and 7 (derived from piperonal, O-benzyl vanillin, and furfural, respectively), showed to be more active than shark cartilage or a-tocopherol. No correlation was found between the protective effect of these nitrones and their log P (partition coefficient) or their capacity to trap OH and CH3 radicals. (c) 2007 Elsevier Ltd. All rights reserved.
• TODA, FUMIO, PURE AND APPL. CHEM., 62,(1990) N, C. 417-422
  作者：TODA, FUMIO

  DOI：——

  日期：——