N-benzylidene<(2)H5>aniline N-oxide | 63710-86-1

• 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-benzylidene<(2)H5>aniline N-oxide
• 英文别名: N,α-diphenyl nitrone；N-benzylidene((2)H5)aniline N-oxide
• CAS: 63710-86-1
• 化学式: C₁₃H₁₁NO
• 分子量: 202.197
• InChiKey: ZEAUJQWDPKRESH-OUHXUHDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.95
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  26.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  N-benzylidene<(2)H5>aniline N-oxide 、 4-bromophenylazotriphenylmethane 以 苯 为溶剂， 反应 0.07h， 生成
  参考文献：
  名称：

  Murofushi, Katsumi; Abe, Kazuhisa; Hirota, Minoru, Journal of the Chemical Society. Perkin transactions II, 1987, p. 1829 - 1834

  摘要：

  DOI：

文献信息

• Rhodium-Catalyzed Cyclization of Diynes with Nitrones: A Formal [2+2+5] Approach to Bridged Eight-Membered Heterocycles
  作者：Chunxiang Wang、Dongping Wang、Hao Yan、Haolong Wang、Bin Pan、Xiaoyi Xin、Xincheng Li、Fan Wu、Boshun Wan

  DOI：10.1002/anie.201407394

  日期：2014.10.27

  N‐aryl‐substituted nitrones were employed as five‐atom coupling partners in the rhodium‐catalyzed cyclization with diynes. In this reaction, the nitrone moiety served as a directing group for the catalytic CH activation of the N‐aryl ring. This formal [2+2+5] approach allows rapid access to bridged eight‐membered heterocycles with broad substrate scope. The results of this study may provide new insight

  在二炔的铑催化环化反应中，N-芳基取代的硝酮被用作五原子偶联伙伴。在该反应中，硝酮部分充当N-芳基环催化CH活化的导向基团。这种正式的[2 + 2 + 5]方法允许快速访问具有广泛底物范围的桥接八元杂环。这项研究的结果可能为硝酮的化学提供新的见解，并发现其在其他杂环的合成中的应用。
• Nitrone Directing Groups in Rhodium(III)-Catalyzed C−H Activation of Arenes: 1,3-Dipoles versus Traceless Directing Groups
  作者：Fang Xie、Songjie Yu、Zisong Qi、Xingwei Li

  DOI：10.1002/anie.201609658

  日期：2016.12.5

  Functionalizable directing groups (DGs) are highly desirable in C−H activation chemistry. The nitrone DGs are explored in rhodium(III)‐catalyzed C−H activation of arenes and couplings with cyclopropenones. N‐tert‐butyl nitrones bearing a small ortho substituent coupled to afford 1‐naphthols, where the nitrone acts as a traceless DG. In contrast, coupling of N‐tert‐butyl nitrones bearing a bulky ortho

  在CH活化化学中，高度可官能化的导向基团（DG）是非常理想的。在铑（III）催化的芳烃的CH活化以及与环丙烯酮的偶联反应中探索了DG酮。N-叔丁基硝酮带有一个小的邻位取代基，偶联生成1-萘酚，其中硝基起无痕DG的作用。相反，带有庞大邻位基团的N-叔丁基硝酮的偶联遵循C–H酰化/ [3 + 2]偶极加成途径生成双环。N-芳基硝酮的偶联遵循相同的酰化/ [3 + 2]加成过程，但传递不同的双环。
• An Unprecedented Formal [5 + 2] Cycloaddition of Nitrones with <i>o</i>-Carboryne via Tandem [3 + 2] Cycloaddition/Oxygen Migration/Aromatization Sequence
  作者：Da Zhao、Jiji Zhang、Zuowei Xie

  DOI：10.1021/jacs.5b09074

  日期：2015.11.4

  molecules. Cycloaddition reaction has created new opportunities to access heterocycles of great complexity due to its advantage of multiple bond formation in a single step. Here, we describe an unprecedented formal [5 + 2] cycloaddition of nitrone with o-carboryne to afford carborane-fused seven-membered heterocycles. Experimental and theoretical data suggest that a sequence of [3 + 2] cycloaddition, N-O

  杂环骨架广泛存在于天然产物和生物活性分子中。由于其在一步中形成多键的优势，环加成反应为获得高度复杂的杂环创造了新的机会。在这里，我们描述了一种前所未有的正式 [5 + 2] 硝酮与邻碳炔的环加成反应，以提供碳硼烷稠合的七元杂环。实验和理论数据表明，这一前所未有的反应涉及一系列 [3 + 2] 环加成、NO 键断裂、氧迁移和重构化。在这个过程中，硝酮部分作为五原子偶联伙伴，两个杂原子都被结合到最终产品的框架中。这种新方法还提供了对硝酮化学的新见解。
• Synthesis of 1,4-epoxy-2-aryltetrahydro-1-benzazepines <i>via</i> rhodium(<scp>iii</scp>)-catalyzed C–H allylation/intramolecular 1,3-dipolar cycloaddition
  作者：Xuan Wang、Jianlong Li、Haifang Du、Weihong Liang、Cheng Luo、Yunshan Wu、Bo Liu

  DOI：10.1039/d3cc05082c

  日期：——

  to 1,4-epoxy-2-aryltetrahydro-1-benzazepine derivatives with high efficiency, namely the Rh(III)-catalyzed C–H allylation of nitrones with allyl precursors, followed by subsequent intramolecular 1,3-dipolar cycloaddition, to deliver the title compounds. This reaction is regio- and stereo-selective, generating the cis-isomer with a broad substrate scope and good functional group tolerance.

  在此，我们报道了一种高效合成1,4-环氧-2-芳基四氢-1-苯并氮杂衍生物的新路线，即Rh( III )-催化硝酮与烯丙基前体的C-H烯丙基化，随后进行分子内1 ,3-偶极环加成，得到标题化合物。该反应具有区域和立体选择性，生成具有广泛底物范围和良好官能团耐受性的顺式异构体。
• Rh(III)-catalyzed coupling of nitrones with alkynes for the synthesis of indolines
  作者：Lingheng Kong、Fang Xie、Songjie Yu、Zisong Qi、Xingwei Li

  DOI：10.1016/s1872-2067(15)60866-x

  日期：2015.7

  Rh-catalyzed redox-neutral coupling between N-aryl nitrones and alkynes has been achieved under relatively mild conditions. The reaction proceeded via C-H activation at the N-aryl ring with subsequent O-atom transfer, affording trisubstituted indolines in good chemoselectivity and moderate to good diasteroselectivity. (C) 2015, Dalian Institute of Chemical Physics, Chinese Academy of Sciences. Published by Elsevier B.V. All rights reserved.