(E)-1-(4-nitrophenyl)-N-phenylmethanimine oxide | 3585-90-8

• 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: (E)-1-(4-nitrophenyl)-N-phenylmethanimine oxide
• 英文别名: (E)-C-p-nitrophenyl-N-phenylnitrone；N-Phenyl-A-(4-nitrophenyl)nitrone；1-(4-nitrophenyl)-N-phenylmethanimine oxide
• CAS: 3585-90-8；87289-89-2；1082725-43-6
• 化学式: C₁₃H₁₀N₂O₃
• 分子量: 242.234
• InChiKey: UVECRWKWUJOHSR-GXDHUFHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.6
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26
• 危险类别码：
  R36/37/38

反应信息

• 作为反应物：
  描述：

  (+)-(3S,4R)-2-benzyl-5-benzyloxycarbonyl-3-phenyl-2,5-diazaspiro[3.4]oct-7-en-1-one 、 (E)-1-(4-nitrophenyl)-N-phenylmethanimine oxide 以 甲苯 为溶剂， 反应 100.0h， 以45%的产率得到(3R,3'S,3a'S,4S,6a'S)-1-benzyl-3'-(4-nitrophenyl)-2-oxo-2',4-diphenyltetrahydrospiro[azetidine-3,4'-pyrrolo[3,4-d]isoxazole]-5'(2'H)-carboxylic acid benzyl ester
  参考文献：
  名称：

  Enantiomerically Pure Polyheterocyclic Spiro-β-lactams from trans-4-Hydroxy-l-proline

  摘要：

  The "Staudinger ketene-imine reaction" between ketenes generated from natural O,N-protected trans-4-hydroxy-L-prolines and the N-benzyl-N-benzylideneamine led to mixtures of diastereoisomeric, enantiomerically pure pyrrolidine-derived spiro-beta-lactams with a relative cis configuration. These were transformed into the corresponding pyrroline-spiro-beta-lactams by means of treatment with a base and the new C = C double bond Was Submitted to a number of different reactions in order to evaluate its reactivity and obtain new polyheterocyclic enantiomerically pure spiro-beta-lactams.

  DOI：

  10.1021/jo100061s

文献信息

• Friedel–Crafts Addition of Indoles to Nitrones Promoted by Trimethylsilyl Trifluoromethanesulfonate
  作者：Zachary Z. Oracheff、Helen L. Xia、Christopher D. Poff、Scott E. Isaacson、C. Wade Downey

  DOI：10.1021/acs.joc.1c01551

  日期：2021.12.3

  Friedel–Crafts addition to aryl and secondary alkyl nitrones in the presence of trimethylsilyl trifluoromethanesulfonate and trialkylamine to produce 3-(1-(silyloxyamino)alkyl)indoles. Spontaneous conversion to bisindolyl(aryl)methanes, which is thermodynamically favored for nitrones derived from aromatic aldehydes, is suppressed under the reaction conditions. The silyloxyamino group can be deprotected with

  在三甲基甲硅烷基三氟甲磺酸酯和三烷基胺存在下， N-烷基吲哚与芳基和仲烷基硝酮进行傅克加成反应生成 3-(1-(甲硅烷氧基氨基)烷基)吲哚。在反应条件下，自发转化为双吲哚基（芳基）甲烷，这在热力学上对于衍生自芳香醛的硝酮是有利的。甲硅烷氧基氨基可以用四丁基氟化铵去保护以产生羟胺。
• Rearrangement of nitrones to amides using chlor0sulfonyl isocyanate
  作者：Sajan P. Joseph、D.N. Dhar

  DOI：10.1016/s0040-4020(01)96081-8

  日期：1986.1

  Reaction of chlorosulfonyl isocyanate (CSI) with nitrones a-n and a,b has been studied. α, α, N-Triaryl nitrones a-n react with CSI to form the N,N-diaryl arylamides a-n and i-n in good yields. In the case of α-H, α, N-diaryl nitrones a,b however, two compounds viz., the rearranged product a,b and the 1,4-dihydro tetrazines a,b are formed.

  研究了氯磺酰基异氰酸酯（CSI）与硝酮an和a，b的反应。α，α，N-三芳基硝酮的与CSI反应以形成N，N-二芳基芳基酰胺的和以良好的收率英寸 然而，在α-H，α，N-二芳基亚硝基a，b中，形成了两种化合物，即重排产物a，b和1，4-二氢四嗪a，b。
• Enantiomerically Pure Polyheterocyclic Spiro-β-lactams from <i>trans</i>-4-Hydroxy-<scp>l</scp>-proline
  作者：Giuseppe Cremonesi、Piero Dalla Croce、Francesco Fontana、Concetta La Rosa

  DOI：10.1021/jo100061s

  日期：2010.3.19

  The "Staudinger ketene-imine reaction" between ketenes generated from natural O,N-protected trans-4-hydroxy-L-prolines and the N-benzyl-N-benzylideneamine led to mixtures of diastereoisomeric, enantiomerically pure pyrrolidine-derived spiro-beta-lactams with a relative cis configuration. These were transformed into the corresponding pyrroline-spiro-beta-lactams by means of treatment with a base and the new C = C double bond Was Submitted to a number of different reactions in order to evaluate its reactivity and obtain new polyheterocyclic enantiomerically pure spiro-beta-lactams.