N-tert-butyl-(2-furfurylideneamine) N-oxide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: N-tert-butyl-(2-furfurylideneamine) N-oxide
• 英文别名: C-2-furyl-N-tert-butyl-nitrone；N-tert-butyl-1-(furan-2-yl)methanimine oxide
• 化学式: C₉H₁₃NO₂
• 分子量: 167.208
• InChiKey: NUSATAQWSPSFJU-YFHOEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  41.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  反式-2-丁烯酸乙酯 、 N-tert-butyl-(2-furfurylideneamine) N-oxide 反应 1.0h， 以76%的产率得到(3RS,4SR,5RS)-2-tert-butyl-3-(2-furyl)-4-carbethoxy-5-methyl-isoxazolidine
  参考文献：
  名称：

  Exploiting microwave-assisted neat procedures: synthesis of N-aryl and N-alkylnitrones and their cycloaddition en route for isoxazolidines

  摘要：

  Microwave irradiation allows increasing the speed of several reactions and also offers the possibility of eliminating poisoning organic solvents. In this work we report the microwave-assisted neat synthesis of alpha-phenyl-tert-butylnitrone (PBN) and other alkyl and aryl nitrones and also the rapid synthesis of isoxazolidines resulting from 1,3-dipolar cycloaddition of nitrones to ethyl trans-crotonate. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.08.101
• 作为产物：
  描述：

  糠醛 、 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 168.0h， 以80%的产率得到N-tert-butyl-(2-furfurylideneamine) N-oxide
  参考文献：
  名称：

  N-tert-Butyl and N-methyl nitrones derived from aromatic aldehydes inhibit macromolecular permeability increase induced by ischemia/reperfusion in hamsters

  摘要：

  N-Alquil nitrones 1c and 3-6 were prepared from aromatic aldehydes and N-tert-butylhydroxylamine or N-methylhydroxylamine in good yields and soft conditions. Their protective effect against microvascular damages caused by ischemia/reperfusion in 'hamster cheek pouch' assay was investigated and compare with that observed for nitrones 1a,b and 2, previously studied. Nitrones 3b, 4b and 4c were the most active ones in inhibiting macromolecular permeability increase induced by ischemia/reperfusion when administered by gavage and intravenous, while 3a and 4a were active only after intravenous administration. N-tert-butylhydroxylamine and Nt-methylhydroxylamine, products of the hydrolysis of these nitrones, were weakly active when administered by gavage or intravenous. Nitrone (4a) was the most potent in inhibiting macromolecular permeability increase induced by histamine. In this case, N-tert-butylhydroxylamine was as active as 4a. The lypophylicity in nitrones, specially in N-methyl nitrones, play an important role on the protective action when compounds were administered by gavage. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2009.04.004

文献信息

• Synthesis and biological evaluation of diastereoisomerically pure N,O-nucleosides
  作者：Olga Bortolini、Antonio De Nino、Tommaso Eliseo、Riccardo Gavioli、Loredana Maiuolo、Beatrice Russo、Fabio Sforza

  DOI：10.1016/j.bmc.2010.08.024

  日期：2010.10

  Several N,O-nucleosides have been synthesized in good yields by direct 1,3-dipolar cyclization methodology, in the absence of solvent. A remarkable cis stereoselectivity (de 98%) was observed by tuning the substituents on the nitrone moiety. A good number of these N,O-nucleosides have been evaluated for cytotoxic activity against selected cellular lines. Some of the tested compounds have proven to

  在不存在溶剂的情况下，通过直接的1，3-偶极环化方法已经以高收率合成了几种N，O-核苷。通过调节硝酮部分上的取代基，观察到了显着的顺式立体选择性（98％）。已经评估了许多这些N，O-核苷对所选细胞系的细胞毒活性。已证明某些测试化合物是潜在的抗增殖药。
• ——
  作者：M. A. Voinov、I. A. Grigor"ev

  DOI：10.1023/a:1015459811377

  日期：——

  The spin-spin coupling constants (3)J(C,H) between the hydrogen atom of the aldonitrone group and the carbon atom bound to the nitrogen atom of the N-oxide fragment were determined for a wide range of cyclic and acyclic aldonitrones. Based on comparison of these constants (trans-(3)J(C,H) (E isomer) > cis-(3)J(C,H) (Z isomer)), the Z configuration was assigned to acyclic nitrones. Coordination of organolithium compounds to the oxygen atom of the N-->O group was revealed by C-13 NMR spectroscopy. This coordination is the necessary condition for the metallation of aldonitrones. The configuration of the nitrone group is responsible for the ability of the E form of acyclic aldonitrones to undergo CD3ONa-catalyzed isotope exchange of the methine proton in CD3OD and metallation with (BuLi)-Li-s.
• 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.
• Exploiting microwave-assisted neat procedures: synthesis of N-aryl and N-alkylnitrones and their cycloaddition en route for isoxazolidines
  作者：Marta M. Andrade、Maria Teresa Barros、Rui C. Pinto

  DOI：10.1016/j.tet.2008.08.101

  日期：2008.11

  Microwave irradiation allows increasing the speed of several reactions and also offers the possibility of eliminating poisoning organic solvents. In this work we report the microwave-assisted neat synthesis of alpha-phenyl-tert-butylnitrone (PBN) and other alkyl and aryl nitrones and also the rapid synthesis of isoxazolidines resulting from 1,3-dipolar cycloaddition of nitrones to ethyl trans-crotonate. (c) 2008 Elsevier Ltd. All rights reserved.
• N-tert-Butyl and N-methyl nitrones derived from aromatic aldehydes inhibit macromolecular permeability increase induced by ischemia/reperfusion in hamsters
  作者：Ayres G. Dias、Carlos E.V. Santos、Fatima Z.G.A. Cyrino、Eliete Bouskela、Paulo R.R. Costa

  DOI：10.1016/j.bmc.2009.04.004

  日期：2009.6

  N-Alquil nitrones 1c and 3-6 were prepared from aromatic aldehydes and N-tert-butylhydroxylamine or N-methylhydroxylamine in good yields and soft conditions. Their protective effect against microvascular damages caused by ischemia/reperfusion in 'hamster cheek pouch' assay was investigated and compare with that observed for nitrones 1a,b and 2, previously studied. Nitrones 3b, 4b and 4c were the most active ones in inhibiting macromolecular permeability increase induced by ischemia/reperfusion when administered by gavage and intravenous, while 3a and 4a were active only after intravenous administration. N-tert-butylhydroxylamine and Nt-methylhydroxylamine, products of the hydrolysis of these nitrones, were weakly active when administered by gavage or intravenous. Nitrone (4a) was the most potent in inhibiting macromolecular permeability increase induced by histamine. In this case, N-tert-butylhydroxylamine was as active as 4a. The lypophylicity in nitrones, specially in N-methyl nitrones, play an important role on the protective action when compounds were administered by gavage. (C) 2009 Published by Elsevier Ltd.