N-(2-phenylpropan-2-yl)-α-(p-methoxyphenyl)nitrone | 280555-27-3

• 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: N-(2-phenylpropan-2-yl)-α-(p-methoxyphenyl)nitrone
• 英文别名: 1-(4-methoxyphenyl)-N-(2-phenylpropan-2-yl)methanimine oxide
• CAS: 280555-27-3；910313-99-4
• 化学式: C₁₇H₁₉NO₂
• 分子量: 269.343
• InChiKey: YNKAQTAPVAVJGZ-AQTBWJFISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  38
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(2-phenylpropan-2-yl)-α-(p-methoxyphenyl)nitrone 在 四甲基乙二胺 、 仲丁基锂 、 三氟乙酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 为溶剂， 反应 48.5h， 生成 (+/-)-(3R,4R,5R)-2-cumyl-5-methyl-4-phenyl-3-p-methoxyphenyl-4,5-epoxy-1,2-oxazin-6-one
  参考文献：
  名称：

  Stereoselective Synthesis of Novel 4,5-Epoxy-1,2-oxazin-6-ones and α,β-Epoxy-γ-amino Acids from β-Lithiated Oxazolinyloxiranes and Nitrones

  摘要：

  A stereoselective synthesis of 9,10-epoxy-1,6-dioxa-4,7-diazaspiro[4,5] decanes has been developed on the basis of the addition of beta-lithiated oxazolinyloxiranes to nitrones. Conversion of these spirocyclic derivatives into 4,5-epoxy-1,2-oxazin-6-ones and successively into alpha,beta-epoxy-amino gamma- acids, alpha-hydroxy-gamma-amino acids, and gamma-butyrolactams is described.

  DOI：

  10.1021/ol0618609
• 作为产物：
  描述：

  Alpha,Alpha-二甲基苄胺 在 sodium tetrahydroborate 、 sodium tungstate 、 双氧水 作用下， 以 甲醇 、 水 、 甲苯 为溶剂， 反应 22.0h， 生成 N-(2-phenylpropan-2-yl)-α-(p-methoxyphenyl)nitrone
  参考文献：
  名称：

  EFFICIENT AND FACILE ROUTES TO NITRONES

  摘要：

  DOI：

  10.1080/00304940009356283

文献信息

• Stereoselective Synthesis of Novel β,γ-Epoxyhydroxylamines and 4-Hydroxyalkyl-1,2-oxazetidines
  作者：Vito Capriati、Saverio Florio、Renzo Luisi、Antonio Salomone、Corrado Cuocci

  DOI：10.1021/ol061256y

  日期：2006.8.1

  A simple and efficient stereoselective synthesis of polysubstituted beta,gamma-epoxyhydroxylamines and 4-hydroxyalkyl-1,2-oxazetidines, based on the addition of alpha-lithiated aryloxiranes to nitrones and subsequent cyclization of the corresponding intermediates in a 4-exo-tet mode, is described.

  一种简单有效的立体选择性合成多取代的β，γ-环氧羟胺和4-羟烷基-1,2-恶唑烷的方法，基于将α-锂化的芳基氧杂环戊烷添加至硝酮并随后将相应的中间体以4-exo-tet模式环化进行说明。
• Asymmetric synthesis of α,β-substituted β-aminoalkanamides and stereochemical determination
  作者：Vito Capriati、Leonardo Degennaro、Saverio Florio、Renzo Luisi、Corrado Cuocci

  DOI：10.1016/j.tetlet.2007.10.035

  日期：2007.12

  prepared by the addition reaction of α-lithiated 2-alkyl-2-oxazolines 9-Li, derived from optically active oxazolines 9, to N-cumyl nitrones 2. The relative stereochemistry of alkanamides 5 and 6 has been established by 1D-NOESY experiments carried out on the related pyrimidinones 7, whereas the absolute configuration of alkanamides 12 and 13 has been confirmed by an X-ray analysis.

  通过使旋光的恶唑啉9衍生的α-锂化的2-烷基-2-恶唑啉9 - Li与N-枯基硝酮2加成反应，可以制备高度对映体富集的β-氨基烷酰胺12和β-苯基氨基烷酰胺13。链烷酰胺5和6的相对立体化学已经通过对相关嘧啶酮7进行的1D-NOESY实验确定，而链烷酰胺12和13的绝对构型已经通过X射线分析得到了证实。
• Oxazoline-mediated highly stereoselective synthesis of α,β-substituted-β-aminoalkanamides, potential precursors of unnatural β2,2,3-amino acids
  作者：Vito Capriati、Leonardo Degennaro、Saverio Florio、Renzo Luisi

  DOI：10.1016/j.tetlet.2007.10.032

  日期：2007.12

  easily transformed into β-amino alkanamides 5 under reductive conditions, whereas acidic hydrolysis with trifluoroacetic acid (TFA) furnishes high yields of β-phenylamino alkanamides 6 via a cumene hydroperoxide-type rearrangement. Derivatives 5 and 6 provide a backbone of potentially useful unnatural β2,2,3-amino acids.

  α-锂化-2-烷基-2-恶唑啉1 - Li与脂族，芳族和杂芳族N-枯基硝酮的反应导致N-枯基-1,6-二氧杂-2,9-二氮杂螺的立体选择性形成[4] ，4]壬烷3与羟氨基衍生物4平衡。这样的平衡混合物可以在还原条件下容易地转化为β-氨基链烷酰胺5，而通过三氟乙酸（TFA）的酸性水解通过枯烯氢过氧化物类型的重排提供了高产率的β-苯基氨基链烷酰胺6。导数5和6提供潜在有用的非天然β2，2，3-氨基酸的骨架。
• EFFICIENT AND FACILE ROUTES TO NITRONES
  作者：Alan R. Katritzky、Xilin Cui、Qiuhe Long、Baozhen Yang、Allan L. Wilcox、Yong-Kang Zhang

  DOI：10.1080/00304940009356283

  日期：2000.4
• Stereoselective Synthesis of Novel 4,5-Epoxy-1,2-oxazin-6-ones and α,β-Epoxy-γ-amino Acids from β-Lithiated Oxazolinyloxiranes and Nitrones
  作者：Vito Capriati、Leonardo Degennaro、Saverio Florio、Renzo Luisi、Pasqualina Punzi

  DOI：10.1021/ol0618609

  日期：2006.10.1

  A stereoselective synthesis of 9,10-epoxy-1,6-dioxa-4,7-diazaspiro[4,5] decanes has been developed on the basis of the addition of beta-lithiated oxazolinyloxiranes to nitrones. Conversion of these spirocyclic derivatives into 4,5-epoxy-1,2-oxazin-6-ones and successively into alpha,beta-epoxy-amino gamma- acids, alpha-hydroxy-gamma-amino acids, and gamma-butyrolactams is described.