N-(4-methoxycarbonylphenyl)-1-phenylmethanimine oxide | 421547-21-9

• 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-(4-methoxycarbonylphenyl)-1-phenylmethanimine oxide
• CAS: 421547-21-9；115399-98-9
• 化学式: C₁₅H₁₃NO₃
• 分子量: 255.273
• InChiKey: NWYAEWDGSVFNNG-WJDWOHSUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  环亚丙基乙酸乙酯 、 N-(4-methoxycarbonylphenyl)-1-phenylmethanimine oxide 以 氘代氯仿 为溶剂， 反应 24.0h， 生成 Ethyl 5-(4-methoxycarbonylphenyl)-6-phenyl-4-oxa-5-azaspiro[2.4]heptane-7-carboxylate
  参考文献：
  名称：

  The powerful effect of N-aryl substitution in promoting the thermal rearrangement of 5-spirocyclopropaneisoxazolidines

  摘要：

  N-Alkyl 5-spirocyclopropaneisoxazolidines rearrange to tetrahydropyridone derivatives by heating. The presence of a phenyl ring on the nitrogen atom significantly reduces the rearrangement temperature. This effect is enhanced by electron-donating substituents and reduced by electron-withdrawing substituents on the phenyl ring. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01339-8
• 作为产物：
  描述：

  对硝基苯甲酸甲酯 在 Rh on carbon calcium chloride 、 肼 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 生成 N-(4-methoxycarbonylphenyl)-1-phenylmethanimine oxide
  参考文献：
  名称：

  The powerful effect of N-aryl substitution in promoting the thermal rearrangement of 5-spirocyclopropaneisoxazolidines

  摘要：

  N-Alkyl 5-spirocyclopropaneisoxazolidines rearrange to tetrahydropyridone derivatives by heating. The presence of a phenyl ring on the nitrogen atom significantly reduces the rearrangement temperature. This effect is enhanced by electron-donating substituents and reduced by electron-withdrawing substituents on the phenyl ring. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01339-8

文献信息

• ¹³C and¹H NMR of Arylnitrones. Substituent Effects of α-Phenyl-<i>N</i>-(<i>p</i>-substituted phenyl)nitrones
  作者：Kohji Suda、Toshio Tsujimoto、Masashige Yamauchi

  DOI：10.1246/bcsj.60.3607

  日期：1987.10

  Substituent effects on the chemical shifts of the conjugation sites in α-phenyl-N-arylnitrones (2) have been investigated. Resonance effects predominate at these positions. The electronic effects of the substituents should be treated separately between electron-donating groups and electron-withdrawing ones. A plausible mechanism for the transmission of the substituent effects in 2 has been proposed.

  研究了取代基对 α-苯基-N-芳基硝基腈 (2) 共轭位点化学位移的影响。共振效应在这些位置上占主导地位。取代基的电子效应应在供电子基团和吸电子基团之间分开处理。研究还提出了 2 中取代基效应传递的合理机制。
• Regio- and stereoselectivity of [2+3]cycloaddition of nitroethene to (Z)-N-aryl-C-phenylnitrones
  作者：Radomir Jasiński

  DOI：10.1135/cccc2009037

  日期：——

  The cycloaddition reactions of nitroethene to (Z)-N-aryl-C-phenylnitrones lead to mixtures of stereoisomeric cis- and trans-2-aryl-4-nitro-3-phenylisoxazolidines. Regioselectivity of these reactions is determined by the character of nucleophile–electrophile interactions, while stereoselectivity is determined by the steric factors and the character of secondary orbital interactions.

  硝基乙烯与（Z）-N-芳基-C-苯基亚硝酮的环加成反应导致产生顺式和反式2-芳基-4-硝基-3-苯基异噁唑啉的立体异构物混合物。这些反应的区域选择性由亲核-电泳子相互作用的性质决定，而立体选择性由立体因素和二次轨道相互作用的性质决定。
• Substituent effect on the [2?+?3] cycloaddition of (E)-?-Nitrostyrene with (Z)-C,N-Diarylnitrones
  作者：Andrzej Baranski

  DOI：10.1002/poc.451

  日期：2002.2

  (ktotal) of the reaction of (E)-β-nitrostyrene (1) with (Z)-C-phenyl-N-arylnitrones (2a–g) was found to increase with increasing Hammett σ-constant, whereas in the case of (Z)-C-aryl-N-phenylnitrones (2g–p) and the same nitrostyrene the rate decreased. The substituent effect in these reactions is inconsistent with FMO treatments of cycloaddition rates. For both reaction series good linear relationships

  通过HPLC在80℃下在甲苯中研究了标题反应的动力学。整体速率常数（ķ总（的反应）ë）-β-硝基苯乙烯（1）与（Ž） - c ^苯基Ñ -arylnitrones（2A-G ）被发现增加随哈米特σ常数，而在（的情况下ž） - c ^ -芳基- ñ -phenylnitrones（2克-p ）和相同的硝基苯乙烯的速率下降。这些反应中的取代基效应与环加成率的FMO处理不一致。对于两个反应系列，log之间均获得了良好的线性关系。k total和通过AM1方法计算的硝酮的> C N（O）-部分中碳原子上的净电荷。版权所有©2001 John Wiley＆Sons，Ltd.
• Copper-Catalyzed Reaction of Terminal Alkynes with Nitrones. Selective Synthesis of 1-Aza-1-buten-3-yne and 2-Azetidinone Derivatives
  作者：Masahiro Miura、Masahiro Enna、Kazumi Okuro、Masakatsu Nomura

  DOI：10.1021/jo00121a018

  日期：1995.8

  Reaction of arylacetylenes with C,N-diarylnitrones using a catalyst system of CuI-dppe (dppe = 1,2-bis(diphenylphosphino)ethane) in the presence of potassium carbonate in DMF predominantly affords the corresponding 1,2,4-triaryl-1-aza- 1-buten-3-ynes in good yields. In contrast, the catalytic reaction using CuI in the presence of an excess amount of pyridine as the ligand gives 1,3,4-triaryl-2-azetidinones as the major products. The reaction with aliphatic terminal alkynes in place of arylacetylenes produces the latter products irrespective of the catalyst system used. Asymmetric induction is also observed in the reaction of phenylacetylene with alpha,N-diphenylnitrone to give 1,2,4-triphenyl-2-azetidinone in the presence of chiral bisoxazoline-type ligands.
• Cordero, Franca M.; Barile, Ingrid; Brandi, Alberto, Synlett, 2000, # 7, p. 1034 - 1036
  作者：Cordero, Franca M.、Barile, Ingrid、Brandi, Alberto、Kozhushkov, Sergei I.、De Meijere, Armin

  DOI：——

  日期：——