C-(2-naphthyl)-N-methylnitrone | 120350-89-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: C-(2-naphthyl)-N-methylnitrone
• 英文别名: (Z)-1-(2-naphtyl)-N-methylmethanimine oxide；(Z)-N-methyl-1-(naphthalen-2-yl)methanimine oxide；(Z)-N-methyl-C-2-naphthyl aldonitrone；Methanamine,N-(2-naphthalenylmethylene)-,N-oxide；N-methyl-1-naphthalen-2-ylmethanimine oxide
• CAS: 120350-89-2
• 化学式: C₁₂H₁₁NO
• 分子量: 185.225
• InChiKey: RWBQOISXVZDXLD-LCYFTJDESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  28.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  C-(2-naphthyl)-N-methylnitrone 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 9.0h， 生成 2-methyl-3-(naphthalen-2-yl)isoxazolidine-4-sulfonic acid allylamide
  参考文献：
  名称：

  Synthesis of Functionalized Sulfonamides via 1,3-Dipolar Cycloaddition of Pentafluorophenyl Vinylsulfonate

  摘要：

  [GRAPHICS]An efficient intermolecular 1,3-dipolar cycloaddition of a variety of nitrones to pentafluorophenyl (PFP) vinylsulfonate is described. The transformation produces stable "reversed" cycloadducts of unprecedented stereo- and regioselectivity. Subsequent amine displacement of the PFP moiety furnished functionalized sulfonamide products in good yields.

  DOI：

  10.1021/ol0347388
• 作为产物：
  描述：

  N-甲基羟胺 、 2-萘甲醛 在 盐酸 、 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 C-(2-naphthyl)-N-methylnitrone
  参考文献：
  名称：

  Synthesis of Functionalized Sulfonamides via 1,3-Dipolar Cycloaddition of Pentafluorophenyl Vinylsulfonate

  摘要：

  [GRAPHICS]An efficient intermolecular 1,3-dipolar cycloaddition of a variety of nitrones to pentafluorophenyl (PFP) vinylsulfonate is described. The transformation produces stable "reversed" cycloadducts of unprecedented stereo- and regioselectivity. Subsequent amine displacement of the PFP moiety furnished functionalized sulfonamide products in good yields.

  DOI：

  10.1021/ol0347388

文献信息

• Asymmetric “Acetylenic” [3+2] Cycloaddition of Nitrones Catalyzed by Cationic Chiral Pd^II Lewis Acid
  作者：Kazuya Honda、Koichi Mikami

  DOI：10.1002/asia.201801016

  日期：2018.10.4

  Highly enantioselective [3+2] cycloaddition of ynones and nitrones has been developed. Very bulky ligand, DTBM‐SEGPHOS, was used for an effective asymmetric induction over distal reaction centers on the linear ynone dipolarophile and for prevention of PdII catalyst deactivation by coordination of the nitrones. The reaction has wide scope of substrates in both ynones and nitrones.

  已经开发出对映体和硝酮的高度对映选择性的[3 + 2]环加成反应。很大体积的配体DTBM-SEGPHOS用于在线性乙炔双极性亲和体的远端反应中心进行有效的不对称诱导，并通过硝酮的配位防止Pd II催化剂失活。该反应在炔酮和硝酮中具有广泛的底物范围。
• (3 + 3) Cycloaddition of Oxyallyl Cations with Nitrones: Diastereoselective Access to 1,2-Oxazinanes
  作者：Marie Cordier、Alexis Archambeau

  DOI：10.1021/acs.orglett.8b00617

  日期：2018.4.20

  Oxyallyl cations are prepared in situ from readily available α-tosyloxy ketones and act as transient electrophilic partners in (3 + 3) cycloaddition with nitrones. Under mild conditions, this method provides a chemoselective and diastereoselective route to polysubstituted 1,2-oxazinanes. A stepwise process is proposed to rationalize the diastereoselectivity of this transformation.

  由容易获得的α-甲苯磺酰氧基原位制备羟基烯丙基阳离子，并在与硝酮的（3 + 3）环加成中充当瞬态亲电子伙伴。在温和的条件下，该方法为多取代的1,2-恶嗪酮提供了化学选择性和非对映选择性的途径。提出了逐步处理以合理化此变换的非对映选择性。
• Regio‐ and Enantioselective (3+3) Cycloaddition of Nitrones with 2‐Indolylmethanols Enabled by Cooperative Organocatalysis
  作者：Tian‐Zhen Li、Si‐Jia Liu、Yu‐Wen Sun、Shuang Deng、Wei Tan、Yinchun Jiao、Yu‐Chen Zhang、Feng Shi

  DOI：10.1002/anie.202011267

  日期：2021.2

  regiospecificity. This approach enabled not only the first organocatalytic asymmetric (3+3) cycloaddition of nitrones but also the first C3‐nucleophilic asymmetric (3+3) cycloaddition of 2‐indolylmethanols. More importantly, theoretical calculations elucidated the role of the cocatalyst HFIP in helping CPA control the reactivity and enantioselectivity of the reaction, demonstrating a new mode of cooperative catalysis

  硝酮与2-吲哚基甲醇的区域和对映选择性（3 + 3）环加成反应是通过六氟异丙醇（HFIP）和手性磷酸（CPA）的协同催化完成的。使用这种方法，以高收率（高达98％），优异的对映选择性（高达96％ee）和排他的区域特异性合成了一系列吲哚稠合的六元杂环。这种方法不仅可以实现硝酮的首次有机催化不对称（3 + 3）环加成反应，而且还可以实现2-吲哚基甲醇的首次C3-亲核不对称（3 + 3）环加成反应。更重要的是，理论计算阐明了助催化剂HFIP在帮助CPA控制反应的反应性和对映选择性方面的作用，证明了一种新型的协同催化方式。
• 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.
• Synthesis of Functionalized Sulfonamides via 1,3-Dipolar Cycloaddition of Pentafluorophenyl Vinylsulfonate
  作者：Stephen Caddick、Hannah D. Bush

  DOI：10.1021/ol0347388

  日期：2003.7.1

  [GRAPHICS]An efficient intermolecular 1,3-dipolar cycloaddition of a variety of nitrones to pentafluorophenyl (PFP) vinylsulfonate is described. The transformation produces stable "reversed" cycloadducts of unprecedented stereo- and regioselectivity. Subsequent amine displacement of the PFP moiety furnished functionalized sulfonamide products in good yields.