(Benzylidenamino)ethansaeure-methylester-N-oxid | 79751-42-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (Benzylidenamino)ethansaeure-methylester-N-oxid
• 英文别名: methyl N-benzylideneglycinate N-oxide；N-(2-methoxy-2-oxoethyl)-1-phenylmethanimine oxide
• CAS: 79751-42-1
• 化学式: C₁₀H₁₁NO₃
• 分子量: 193.202
• InChiKey: RTQRSPCHGBZIAE-UHFFFAOYSA-N

物化性质

• 沸点：
  329.6±44.0 °C(Predicted)
• 密度：
  1.164±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  (Benzylidenamino)ethansaeure-methylester-N-oxid 在 potassium tert-butylate 作用下， 以 甲苯 为溶剂， 反应 2.0h， 生成 2-Methyl-6-phenyl-1-aza-7-oxabicyclo<2.2.1>heptan-2-carbonsaeure-methylester
  参考文献：
  名称：

  Lau, Hans-Hermann; Schoellkopf, Ulrich, Liebigs Annalen der Chemie, 1981, # 8, p. 1378 - 1387

  摘要：

  DOI：
• 作为产物：
  描述：

  苯甲醛肟 、 溴乙酸甲酯 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以75%的产率得到(Benzylidenamino)ethansaeure-methylester-N-oxid
  参考文献：
  名称：

  Lau, Hans-Hermann; Schoellkopf, Ulrich, Liebigs Annalen der Chemie, 1981, # 8, p. 1378 - 1387

  摘要：

  DOI：

文献信息

• Nitrone Ylides: Two Possible 1,3-Dipolar Cycloadditions but Only One Stepwise Formation of all-cis-5-Aryl-2,3,5-trisubstituted N-Hydroxypyrrolidines
  作者：Pedro Merino、Tomás Tejero、Alba Díez-Martínez、Zeynep Gültekin

  DOI：10.1002/ejoc.201101035

  日期：2011.11

  all-cis-N-hydroxypyrrolidines has been developed through the formal [3+2] dipolar cycloaddition of electron-poor alkenes and nitrone ylides generated from N-(methoxycarbonylmethyl)nitrones. Treatment of the nitrone with a tertiary amine in the presence of either a lithium salt or butyllithium followed by addition of the alkene at low temperature provided the product in very good chemical yield and excellent

  通过由 N-（甲氧基羰基甲基）硝酮生成的缺电子烯烃和硝酮叶立德的正式 [3+2] 偶极环加成反应，开发了一种合成全顺式 N-羟基吡咯烷的有效方法。在锂盐或丁基锂的存在下用叔胺处理硝酮，然后在低温下加入烯烃，以非常好的化学产率和优异的非对映选择性提供产物。关键中间体的分离和表征表明，该反应是一个逐步过程，由初始迈克尔加成和分子内曼尼希型反应组成。
• Catalytic Migratory Oxidative Coupling of Nitrones
  作者：Shogo Hashizume、Kounosuke Oisaki、Motomu Kanai

  DOI：10.1021/ol201629n

  日期：2011.8.19

  bond-formation proceeds through cleavage of two C(sp3)–H bonds concomitant with C═N double bond-migration. The reaction provides an alternating nitrone moiety, allowing for further synthetically useful transformations. Radical clock studies suggest that the nucleophilic addition of nitrones to an oxidatively generated carbocation is a key step.

  描述了在硝基和杂环或甲胺之间的Cu（I）催化的迁移氧化偶联。选择性的C–C键形成是通过裂解两个C（sp 3）–H键以及C═N双键迁移而进行的。该反应提供了交替的硝酮部分，允许进一步合成有用的转化。自由基钟的研究表明，将硝酮亲核加成到氧化生成的碳正离子上是关键的一步。
• Stereoselective Photoredox Catalyzed (3+3) Dipolar Cycloaddition of Nitrone with Aryl Cyclopropane
  作者：Yao Xu、Hai‐Xiang Gao、Chengkai Pan、Yue Shi、Chi Zhang、Genping Huang、Chao Feng

  DOI：10.1002/anie.202310671

  日期：2023.10.26

  A radical type (3+3) cycloaddition of cyclopropane is realized with aryl cyclopropane and nitrone under photoredox catalysis in a highly regio- and diastereoselective manner. The reaction includes a stereospecific three-electron-type nucleophilic ring opening and a 6-endo-trig radical cyclization.

  在光氧化还原催化下，芳基环丙烷和硝酮以高度区域和非对映选择性的方式实现了环丙烷的自由基型(3+3)环加成。该反应包括立体特异性三电子型亲核开环和6-内三自由基环化。
• A combined experimental (XRD, FT-IR, UV-VIS and NMR) and theoretical (NBO, NLO, local &amp; global chemical activity) studies of methyl 2-((3R,4R)-3-(naphthalen-1-yl)-4-(phenylsulfonyl) isoxazolidin-2-yl) acetate
  作者：Zeynep Gültekin、Zeynep Demircioğlu、Wolfgang Frey、Orhan Büyükgüngör

  DOI：10.1016/j.molstruc.2019.126970

  日期：2020.1

  Methyl 2-((3R,4R)-3-(naphthalen-1-yl)-4-(phenylsulfonyl) isoxazolidin-2-yl) acetate (3e) was synthesized and characterized by XRD, FT-IR, UV-Vis and NMR techniques. All theoretical computations were calculated by using density functional theory (DFT) B3LYP method with the help of 6-311G(d,p) basis set. Theoretical calculations help to obtain detailed information about local & global chemical activities, molecular and chemical properties which are reveal the electrophilic and nucleophilic nature. Accordingly, global (FMOs, hardness & softness parameters) and local (MEP, FF, net charges) chemical activity descriptors were examined. To determine the non-linear optical behaviours of title compound; the total dipole moment, mean polarizability and first-order hyperpolarizability values have been examined. (C) 2019 Published by Elsevier B.V.
• Lau, Hans-Hermann; Schoellkopf, Ulrich, Liebigs Annalen der Chemie, 1981, # 8, p. 1378 - 1387
  作者：Lau, Hans-Hermann、Schoellkopf, Ulrich

  DOI：——

  日期：——