(3-(4-bromophenyl)aziridin-2-yl)(phenyl)methanone | 77472-76-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3-(4-bromophenyl)aziridin-2-yl)(phenyl)methanone
• 英文别名: trans-2-benzoyl-3-(4-bromophenyl)aziridine；[trans-3-(4-bromo-phenyl)-aziridin-2-yl]-phenyl ketone；[trans-3-(4-Brom-phenyl)-aziridin-2-yl]-phenyl-keton；[(2S,3R)-3-(4-bromophenyl)aziridin-2-yl]-phenylmethanone
• CAS: 77472-76-5
• 化学式: C₁₅H₁₂BrNO
• 分子量: 302.17
• InChiKey: KBGOQVUCMFYENS-KGLIPLIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  39
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3-(4-bromophenyl)aziridin-2-yl)(phenyl)methanone 在 三氟化硼乙醚 作用下， 以 丙酮 为溶剂， 以83%的产率得到
  参考文献：
  名称：

  Boron fluorides of cis- and trans-2-aryl-3-aroylaziridines

  摘要：

  DOI：

  10.1007/bf00473451
• 作为产物：
  描述：

  4′-溴查耳酮 在 sodium hydride 、 N,N'-Diamino-1,4-diazoniabicyclo<2.2.2>octane Dinitrate 作用下， 以 异丙醇 、 苯 为溶剂， 以76%的产率得到(3-(4-bromophenyl)aziridin-2-yl)(phenyl)methanone
  参考文献：
  名称：

  Direct NH-aziridination of α,β-unsaturated ketones

  摘要：

  1-芳基-α,β-不饱和酮在氢化钠存在下，由氮-氮亚胺前驱体N,N'-二氨基-1,4-二氮双环[2.2.2]八烷二硝酸盐通过一锅反应直接进行未取代的氮杂环化，获得了令人满意的产率。

  DOI：

  10.1039/b200046f

文献信息

• Direct <i>N</i>-Me Aziridination of Enones
  作者：Jawahar L. Jat、Ajay K. Yadav、Chandra Bhan Pandey、Dinesh Chandra、Bhoopendra Tiwari

  DOI：10.1021/acs.joc.1c02785

  日期：2022.3.4

  The first direct general method for N-Me aziridination of electron-deficient olefins, enones, is described using N-methyl-O-tosylhydroxylamine as the aminating agent in the presence of a Cu(OTf)2 catalyst. The aziridination of vinyl ketones, hitherto unknown for N-Me as well as N-H, has been achieved efficiently. The open-flask reaction is stereospecific, operationally simple, and additive-free. It

  描述了在Cu(OTf) 2催化剂存在下使用N-甲基-O-甲苯磺酰基羟胺作为胺化剂，对缺电子烯烃烯酮进行N -Me氮丙啶化的第一种直接通用方法。N -Me 和N -H迄今未知的乙烯基酮的氮丙啶化已有效实现。开瓶反应具有立体特异性、操作简单且无添加剂。它还在类似的反应条件下有效地提供了N -H 氮丙啶化产物。
• Regio- and stereo-selective ring expansion of keto-aziridines to the corresponding thiomorpholines
  作者：Fatemeh Khodadadi、Heshmat Allah Samimi、Jalal Albadi、Ahmadreza Momeni

  DOI：10.1080/17415993.2021.1914044

  日期：2021.9.3

  In this research, an efficient process for the synthesis of the some novel 3-thiomorpholines from a regio- and stereo-selective reaction of ketoaziridines with 2-mercaptoacetic acid in the presence of dicyclohexyl carbodiimide is reported. A plausible mechanism has been proposed.

  在这项研究中，报道了在二环己基碳二亚胺存在下，酮氮丙啶与 2-巯基乙酸的区域和立体选择性反应合成一些新型 3-硫代吗啉的有效方法。已经提出了一种合理的机制。
• K5[PW11ZnO39].23H2O-catalyzed acylation/ring expansion of ketoaziridines in a single pot: a new regio- and stereo-selective route for the synthesis of oxazolines
  作者：Heshmat A. Samimi、Akram Mostafavi、Mostafa Riahi Farsani

  DOI：10.1007/s13738-015-0678-9

  日期：2015.11

  A new and one-pot synthesis of oxazolines has been accomplished by K5[PW11ZnO39].23H2O—catalyst acylation followed by C–N ring opening/C–O bond formation in NH ketoaziridines. This regio- and stereo-selective reaction presumably proceeds via a domino sequence resulting in the in situ generation of acyl aziridine which undergoes a ring expansion reaction via an initial C–N rupture of aziridine ring

  通过K 5 [PW 11 ZnO 39 ] .23H 2 O-催化剂酰化，然后在NH酮氮丙啶中进行C-N开环/ C-O键形成，完成了一种新的一锅法合成恶唑啉。这种区域选择性和立体选择性反应大概是通过多米诺序列进行的，从而导致酰基氮丙啶的原位生成，然后通过氮丙啶环的最初C–N断裂，随后闭环形成恶唑啉，进行环扩环反应。该方法为反式-2,5-二芳基-4-芳基恶唑啉的合成提供了新颖的一锅法。
• KI-catalyzed ring expansion reaction of trans -NH-ketoaziridines to new trans -oxazolidines
  作者：Heshmat A. Samimi、Bohari M. Yamin

  DOI：10.1016/j.tetlet.2015.12.025

  日期：2016.1

  In this work, the synthesis of a new class of trans-oxazolidines by the regio- and stereocontrolled reaction of NH-ketoaziridines with phenylisocyanate is reported. A plausible mechanism has been proposed.

  在这项工作中，报道了通过NH-酮氮丙啶与苯基异氰酸酯的区域和立体控制反应合成一类新型的反-恶唑烷。已经提出了一种合理的机制。
• Efficient Aziridination of α,β-Unsaturated Ketones with<i>O</i>-(2,4-Dinitrophenyl)-hydroxylamine
  作者：Jin-jia Wang、Jin-hua Lao、Xue-ming Li、Rui-jiong Lu、Hui Miao、Ming Yan

  DOI：10.1080/00397911.2010.541968

  日期：2012.6

  The aziridination of alpha,beta-unsaturated ketones with O-(2,4-dinitrophenyl)-hydroxylamine and tertiary amine was developed. trans-Aziridines were obtained exclusively in good yields. The reaction is proposed to occur via an aminimide intermediate.