N-methyl,α-(4-dimethylamino)phenyl nitrone | 203731-12-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-methyl,α-(4-dimethylamino)phenyl nitrone
• 英文别名: N,N-dimethyl-4-[((Z)-methyl-oxy-amino)-methyl]-aniline；1-[4-(dimethylamino)phenyl]-N-methylmethanimine oxide
• CAS: 203731-12-8；33184-68-8；16089-69-3
• 化学式: C₁₀H₁₄N₂O
• 分子量: 178.234
• InChiKey: ABKOTZUEXDIEIB-WQLSENKSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  32
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-methyl,α-(4-dimethylamino)phenyl nitrone 生成 trans-3-p-Dimethylaminophenyl-2-methyl-oxaziridin
  参考文献：
  名称：

  硝酮-恶氮丙啶系统中的轨道对称控制。硝酮光稳态

  摘要：

  最近的轨道对称规则已被证明适用于杂原子系统，例如硝酮热环加成反应以及 CC 键处的热和光化学氮丙啶环裂解。在这些具有四个 {pi} 电子的分子中，协同的光环化是反旋转的，而反向热裂解是旋转的。与偶氮甲碱叶立德-氮丙啶系统相反，硝酮光环化成恶氮丙啶的立体化学只能在碳和氮原子上观察到，因为氧原子具有孤对电子而不是取代基。对于 oxaziridine 对硝酮的反向热开环，CO 键断裂的两种可能的旋转运动应该导致硝酮的顺式和反式异构体的混合物，这与应该是立体有择的光闭合相反。

  DOI：

  10.1021/ja00745a057
• 作为产物：
  描述：

  对二甲氨基苯甲醛 在 三氟甲磺酸三甲基硅酯 作用下， 以 苯 为溶剂， 反应 70.0h， 生成 N-methyl,α-(4-dimethylamino)phenyl nitrone
  参考文献：
  名称：

  An efficient method for the generation of N-methyl nitrones

  摘要：

  DOI：

  10.1021/jo00350a110

文献信息

• Electronic effects in 1,3-dipolar cycloaddition reactions of N-alkyl and N-benzyl nitrones with dipolarophiles
  作者：Andrei Bădoiu、E. Peter Kündig

  DOI：10.1039/c1ob06144e

  日期：——

  1,3-Dipolar cycloadditions afforded fast access to isoxazolidines bearing N-alkyl or N-benzyl substituents. The electronic properties of the substituents in the nitrones define the activity of the dipoles and modulate diastereoselectivity in the non-catalyzed reactions. Using a chiral one-point binding ruthenium Lewis acid catalyst, products were obtained in good yields and with excellent regio-, diastereo-

  1，3-偶极环加成可快速接近带有N-烷基或N-苄基取代基的异恶唑烷。硝酮中取代基的电子性质定义了偶极子的活性，并调节了非催化反应中的非对映选择性。使用手性单点结合钌路易斯酸催化剂，可以以良好的收率和优异的区域，非对映和对映选择性获得产物。
• Synthesis and structure–antibacterial activity relationship investigation of isomeric 2,3,5-substituted perhydropyrrolo[3,4-d]isoxazole-4,6-diones
  作者：Hikmet Agirbas、Selahaddin Guner、Fatma Budak、Sema Keceli、Fatma Kandemirli、Nathaly Shvets、Vasyl Kovalishyn、Anatholy Dimoglo

  DOI：10.1016/j.bmc.2007.01.029

  日期：2007.3

  es with N-substituted maleimides. The compounds were screened for their antibacterial activities and most of them exhibited activity against Enterococcus faecalis (ATCC 29212) and Staphylococcus aureus (ATCC 25923). cis-3a and cis-3d were found fairly effective against E. faecalis (ATCC 29212) and S. aureus (ATCC 25923) with MIC values of 25 and 50microg/ml. With the changes of cis isomers of the compounds

  2,3,5-取代的全氢吡咯并[3,4-d]异恶唑-4,6-二酮（44种化合物）的合成已通过N-甲基-C-芳基亚硝基与N-取代的马来酰亚胺的环加成反应完成。筛选了化合物的抗菌活性，并且大多数化合物表现出对粪肠球菌（ATCC 29212）和金黄色葡萄球菌（ATCC 25923）的活性。发现cis-3a和cis-3d对屎肠球菌（ATCC 29212）和金黄色葡萄球菌（ATCC 25923）相当有效，MIC值为25和50microg / ml。随着化合物顺式异构体的转变，其抗菌活性也随之改变。首先，已经根据电子拓扑方法（ETM）的规则计算了药效学片段。下一个，活性化合物和药效基团都已被投影到Kohonen自组织图（SOM）的节点上，以获取药效基团片段的权重作为数值描述符，此后用于关联神经网络（ASNN）训练。作为训练ASNN的结果，开发了用于活动预测的模型。
• 10.1016/j.molstruc.2024.138624
  作者：Lasri, Jamal、Soliman, Saied M.、Ali, Ehab M.M.、Eltayeb, Naser E.、Dege, Necmi、Donia, Thoria、Khamis, Abeer A.、Alzahrani, Faisal Ay.

  DOI：10.1016/j.molstruc.2024.138624

  日期：——

  and (Z)–N-methyl-C-4-substituted phenyl aldonitrones 2 and 3 were synthesised and fully characterised. With the help of Hirshfeld calculations, the molecular packing of 1 is found to be controlled by short N…H contacts (28.3%) in addition to the aromatic π-π stacking where the%C…C interactions is calculated to be 9.7%. In this case, the second most abundant interaction is H…H contact (28.1%). For 2,

  合成并充分表征了 (E)-4-氰基苯甲醛肟 1 和 (Z)-N-甲基-C-4-取代的苯基醛硝酮 2 和 3。借助 Hirshfeld 计算，发现 1 的分子堆积除了芳香 π-π 堆积之外还受到短 N…H 接触 (28.3%) 的控制，其中 %C…C 相互作用计算为 9.7%。在这种情况下，第二丰富的相互作用是 H…H 接触 (28.1%)。对于2，N…H (24.4%) 和O…H (13.8%) 接触是最重要的，而最丰富的相互作用是H…H 接触(36.0%)。利用 DFT 计算来探索两种化合物在优化几何形状下的结构和电子参数，发现这些参数与 X 射线结构非常一致。 2 (6.9829 Debye) 的结构比 1 (4.5282 Debye) 的极性更强。化合物 1-3 降低了 MCF-7 和 T47D 的生长。化合物1对MCF-7和T47D细胞系具有最低的IC50值，被认为是最有前途的抗癌药物。检查了化合物
• Chromium and Tungsten Pentacarbonyl Groups as Reactivity and Selectivity Auxiliaries in [3 + 2] Cycloaddition of Alkynyl Fischer Carbene Complexes with N-Alkyl Nitrones
  作者：Kin Shing Chan、Ming Lok Yeung、Wai-kin Chan、Ru-Ji Wang、Thomas C. W. Mak

  DOI：10.1021/jo00111a036

  日期：1995.3

  Alkynyl Fischer carbene complexes were found to undergo chemoselective, regioselective, and rate-enhanced 1,3-dipolar cycloaddition with nitrones to give 2,3-dihydroisoxazole carbene complexes in excellent yields. These alkynyl complexes can serve as synthons for substituted propiolate esters since the metal pentacarbonyl group of the cycloadducts can be easily oxidatively removed with DMSO. The tungsten carbene complex 4b reacted with 3 different series of N-alkyl nitrones: N-tert-butyl 2a-f, N-methyl 1a-h and N-benzyl 3 to give cycloadducts 6a-f, 7a-h, and 8-9, respectively, while the chromium carbene complex 4a reacted only with N-tert-butyl nitrones 2a-g to give isolable cycloadducts 5a-g. The structure of N-methyl cycloadduct 7d has been established by a single-crystal X-ray analysis. The reactivity of N-alkyl nitrones toward carbene complexes was in the order: N-Me > N-Bn > N-(t)Bu. In addition, our results showed that the rate of cycloaddition reaction increased as the electron donating ability of para-substituent in N-tert-butyl nitrone 2a-f increased.
• Palladium-catalysed cascade molecular queuing-cycloaddition, cyclocondensation and Diels–Alder reactions
  作者：Ronald Grigg、Angela Liu、Duncan Shaw、Selvaratnam Suganthan、Melanie L Washington、Diane E Woodall、Gnanamoly Yoganathan

  DOI：10.1016/s0040-4039(00)01177-1

  日期：2000.9

  The locked s-cis enone system present in 3-methylenequinol-4-ones and chroman-4-ones offers substantial further synthetic opportunities as illustrated by the ability to function as a 2 pi-component in 1,3-dipolar cycloaddition reactions, or as a 2 pi- or 4 pi-component in Diels-Alder reactions. Cascade molecular queuing-cycloadditions/cyclocondensation are reported. (C) 2000 Elsevier Science Ltd. All rights reserved.