2-甲基-3-苯基氧杂吖丙啶 | 3400-12-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-甲基-3-苯基氧杂吖丙啶
• 英文名称: 2-methyl-3-phenyl-oxaziridine
• 英文别名: 2-methyl-3-phenyl-1,2-oxaziridine；2-Methyl-3-phenyl-oxaziridin；Oxaziridine, 2-methyl-3-phenyl-；2-methyl-3-phenyloxaziridine
• CAS: 3400-12-2；39245-63-1；40264-03-7；67462-99-1；67463-00-7；182824-63-1
• 化学式: C₈H₉NO
• 分子量: 135.166
• InChiKey: GDAZZZLHHSQPOQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  15.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-甲基-3-苯基氧杂吖丙啶 在 氢气 作用下， 以 二氯甲烷 为溶剂， 生成 N-甲基-C-苯基硝酮
  参考文献：
  名称：

  四氟硼酸叔胺和亚胺的作用

  摘要：

  衍生自二氢异喹啉的恶唑烷鎓盐1是向伯胺的氧转移试剂，伯胺可导致亚硝基衍生物（如果R =烷基）或硝基化合物（如果R =芳基），叔胺导致N-氧化物，仲胺和亚胺导致到相应的硝酮。

  DOI：

  10.1016/s0040-4020(01)89569-7
• 作为产物：
  描述：

  N-methyl-α-phenylnitrone 以 氘代丙酮 为溶剂， 反应 72.0h， 生成 2-甲基-3-苯基氧杂吖丙啶
  参考文献：
  名称：

  光化学诱导的叔胺和硝酮之间的CC键形成†

  摘要：

  在叔胺存在下，光激发的硝酮既是出色的电子受体，又是自由基受体，通过光化学诱导的叔胺的直接sp 3 C–H官能化作用生成β-氨基羟胺。有机光敏剂和光辐射的组合使用在加速加成反应方面非常有效。成功地利用了几种硝酮和叔胺，以高收率得到了β-氨基羟胺。成功实现了基于Lewis立体电子规则的高区域选择性生成伯α-氨基烷基自由基，以及伯α-氨基烷基自由基与硝酮的非对映选择性加成反应。此外，α-氨基烷基自由基与手性（进行E）-几何固定的α-烷氧基羰基亚硝基。

  DOI：

  10.1039/c5ob01277e

文献信息

• An Environmentally Friendly Oxidation System for the Selective Oxygenation of Aldimines to Oxaziridines with Anhydrous TBHP and Alumina-Supported MoO3 as a Recyclable Heterogeneous Catalyst
  作者：Sweety Singhal、Suman L. Jain、V. V. D. N. Prasad、Bir Sain

  DOI：10.1002/ejoc.200600980

  日期：2007.5

  A highly efficient and selective protocol for the oxygenation of various aldimines to oxaziridines, which proceeds in excellent yields with enhanced selectivity by using alumina-supported MoO3 as a recyclable heterogeneous catalyst and anhydrous TBHP as the ultimate oxidant, is described. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

  描述了一种将各种醛亚胺氧化成恶氮丙啶的高效和选择性方案，该方案通过使用氧化铝负载的 MoO3 作为可回收的多相催化剂和无水 TBHP 作为最终氧化剂，以优异的产率和更高的选择性进行。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
• [Bmim]BF4-immobilized rhenium-catalyzed highly efficient oxygenation of aldimines to oxaziridines using solid peroxides as oxidants
  作者：Suman L. Jain、Sweety Singhal、Bir Sain

  DOI：10.1016/j.jorganchem.2007.03.004

  日期：2007.6

  Various rhenium-based catalysts immobilized in [bmim]BF4 were found to be efficient for oxygenation of various aldimines to the corresponding oxaziridines in excellent yields under mild conditions using solid peroxides like UHP, SPC and SPB as oxidants. Among the various rhenium-based catalysts studied, MTO was found to be most efficient. The reusability and recyclability of MTO immobilized in [bmim]BF4 was established by using it for three subsequent cycles for oxygenation of benzylidine-tert-butylamine using UHP as oxidant. (C) 2007 Elsevier B.V. All rights reserved.
• Ring Expansion of Donor–Acceptor Cyclopropane via Substituent Controlled Selective <i>N</i>-Transfer of Oxaziridine: Synthetic and Mechanistic Insights
  作者：Asit Ghosh、Subhajit Mandal、Pratim Kumar Chattaraj、Prabal Banerjee

  DOI：10.1021/acs.orglett.6b02417

  日期：2016.10.7

  A distinctive N-substituent controlled electrophilic N-transfer of oxaziridines with donor-acceptor cyclopropanes in the presence of MgI2 is reported. Contrary to earlier reports, the oxaziridine having bulkier N-substituents can also give N-transferred product instead of the O-transferred one. Interestingly, the oxaziridines having alpha-H containing N-substituents lead to the pyrrolidine derivatives through [3 + 2] cycloaddition. A mechanistic reasoning for this divergent reactivity 18 depicted by density functional theory calculations and validated through energy decomposition analysis.
• Photochemical Beckmann rearrangements. Correspondence between substituent effects in oximes and oxaziridines
  作者：Yoshiro Ogata、Katsuhiko Takagi、Kiyohiko Mizuno

  DOI：10.1021/jo00140a019

  日期：1982.9
• Reaction of oxaziridine with heterocumulene. A ketene, isocyanates, and carbodiimide
  作者：Mitsuo Komatsu、Yoshiki Ohshiro、Hiroshi Hotta、Masaaki Sato、Toshio Agawa

  DOI：10.1021/jo00921a020

  日期：1974.4