1,2-dimethyl-3-phenylaziridine | 124919-00-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1,2-dimethyl-3-phenylaziridine
• 英文别名: (2S,3R)-1,2-Dimethyl-3-phenylaziridine；cis-(2S,3R)-1,2-dimethyl-3-phenylaziridine；(-)cis-(2S:3R)-N-Methyl-2-methyl-3-phenylaziridin；(2S,3R)-cis-1,2-dimethyl-3-phenylaziridine；(2S)-1,2r-dimethyl-3c-phenyl-aziridine；(2S)-1,2r-Dimethyl-3c-phenyl-aziridin；(2R,3S)-1,3-dimethyl-2-phenylaziridine
• CAS: 124919-00-2
• 化学式: C₁₀H₁₃N
• 分子量: 147.22
• InChiKey: MKCZABZZOZOQTK-AZXCQMJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,2-dimethyl-3-phenylaziridine 在 萘 、 重水 、 lithium 作用下， 以 四氢呋喃 为溶剂， 以85%的产率得到(1R,2S)-2-(Methylamino)-1-deuterio-1-phenylpropane
  参考文献：
  名称：

  N,2-Dilithioalkylamines from Aziridines by Naphthalene-Catalyzed Reductive Opening. Synthetic Applications

  摘要：

  The reductive opening of aziridines 1a-c with lithium in the presence of a catalytic amount of naphthalene at -78 degrees C led to the corresponding dianionic intermediates 2a-c, which are stable species under these reaction conditions and react with electrophilic reagents [H2O, D2O, Me(2)S(2), Bu(t)CHO, PhCHO, Me(2)CO, (CH2)(5)CO, (EtO)(2)CO, CH2=CHCO(2)Me, PhCON(CH2)(4), PhCH=NPh, MeI, and CH2=CHCH2Br] to give, after hydrolysis with water, the corresponding difunctionalized compounds 3-5. When the reductive opening and the reaction with electrophiles [H2O, D2O, CH2=CHCH2Br, Me(2)CO, (c-C3H5)(2)CO] were carried out on chiral aziridines 8 and 9, enantiomerically pure difunctionalized compounds 12 were obtained with same stereochemistry, independently of the stereochemistry of diastereomeric starting aziridines 8 and 9.

  DOI：

  10.1021/jo00090a044
• 作为产物：
  描述：

  (1S,2S)-N-甲基-1-苯基-1-氯-2-丙胺 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 生成 1,2-dimethyl-3-phenylaziridine
  参考文献：
  名称：

  Efficient synthesis of cis-thiazolidinethiones derived from ephedrines

  摘要：

  The reaction of chlorodeoxypseudoephedrine or chlorodeoxynorpseudoephedrine hydrochlorides with sodium dithiocarbonate in stirring ethanol at 0 degrees C to stereoselectively afford the corresponding cis-thiazolidinethiones in good yields (81% and 95%) is reported. The in situ formation of a cis-aziridine to explain the presence of trans-thiazolidinethione as a side product is proposed when the same reaction was carried out at room temperature. In addition, a 70:30 mixture of trans-isomers of a thiazolidinethione/isothiazolidinethione was formed when a cis-aziridine NH was reacted with carbon disulfide in refluxing ethanol. The analogous reaction with cis-aziridine N-Me stereoselectively affords the corresponding cis-thiazolidinethione. The H-1 and C-13 NMR data of the thiazolidinethiones were assigned. cis-3,4-Dimethyl-5-phenylthiazolidine-2-thione was crystallized from ethanol and its X-ray diffraction structure was analyzed. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.02.016

文献信息

• Stereospecific Alkene Aziridination Using a Bifunctional Amino-Reagent: An Aza-Prilezhaev Reaction
  作者：Joshua J. Farndon、Tom A. Young、John F. Bower

  DOI：10.1021/jacs.8b10485

  日期：2018.12.26

  deprotection (TFA) of O-Ts activated N-Boc hydroxylamines triggers intramolecular aziridination of N-tethered alkenes to provide complex N-heterocyclic ring systems. Synthetic and computational studies corroborate a diastereospecific aza-Prilezhaev-type mechanism. The feasibility of related intermolecular alkene aziridinations is also demonstrated.

  O-Ts 活化的 N-Boc 羟胺的原位脱保护 (TFA) 触发了 N-系链烯烃的分子内氮丙啶化，以提供复杂的 N-杂环系统。合成和计算研究证实了一种非对映特异性 aza-Prilezhaev 型机制。还证明了相关分子间烯烃氮丙啶的可行性。
• Experimental and theoretical investigations for the regio and stereoselective transformation of trans 1,2,3-trisubstituted aziridines into trans oxazolidin-2-ones
  作者：Luisa Testa、Mohamed Akssira、Elena Zaballos-Garcı́a、Pau Arroyo、Luis R Domingo、Jose Sepúlveda-Arques

  DOI：10.1016/s0040-4020(02)01565-x

  日期：2003.1

  The regio and stereoselective transformation of trans 1,2,3-trisubstituted aziridines into trans oxazolidin-2-ones takes place in good yield. However, the cis configuration at C2 and C3 in monocyclic aziridines is a limiting factor for this transformation. Ab initio calculations show that while the ring-opening process assisted by iodide is regioselective, the subsequent ring-closure is responsible

  反式1,2,3-三取代的氮丙啶类化合物的区域和立体选择性转化为反式恶唑烷丁-2-酮的收率很高。但是，单环氮丙啶中C2和C3处的顺式构型是该转化的限制因素。从头算计算表明，尽管碘化物辅助的开环过程具有区域选择性，但随后的闭环是反式恶唑烷二-2-酮构型保持的原因。在顺式氮丙啶的闭环过程中发现的较大能量解释了不形成顺式恶唑烷丁-2-酮的原因。
• Asymmetric synthesis of phosphinates, phosphine oxides and phosphines by Michaelis Arbuzov rearrangement of chiral oxazaphospholidine
  作者：S. Juge、J.P. Genet

  DOI：10.1016/s0040-4039(00)99124-x

  日期：1989.1

  A general approach to asymmetric synthesis of high optically active tertiary organophosphorus compounds is described. Oxazaphospholidine reacts with alkyl halide to give regio and stereoselectively the corresponding phosphinamide . Methyl phenyl phosphinamide is used for the preparation of methyl phenyl phosphinate with ee > 96%. The preparation of (+) and (−) - PAMP or DIPAMP from is described.

  描述了不对称合成高旋光性叔有机磷化合物的一般方法。氧杂膦烷与卤代烷反应生成区域立体选择性的膦酰胺。甲基苯基次膦酰胺用于制备ee> 96％的苯基苯基次膦酸甲酯。描述了（+）和（-）-PAMP或DIPAMP的制备。
• α- vs Ortho-Lithiation of <i>N</i>-Alkylarylaziridines: Probing the Role of the Nitrogen Inversion Process
  作者：Francesco Affortunato、Saverio Florio、Renzo Luisi、Biagia Musio

  DOI：10.1021/jo8016549

  日期：2008.12.5

  the aziridine nitrogen lone-pair has been considered: dynamics at the aziridine nitrogen as well as complex-induced proximity effects seem to be responsible for the observed regioselectivity in both monophenyl and diphenylaziridines. It turns out that, by tuning the reaction conditions for the lithiation of trans-1-alkyl-2-methyl-3-phenylaziridines, it is possible to generate with high regioselectivity

  已经对单苯基和二苯基氮丙啶的锂化反应进行了详细研究，以了解为什么前者仅进行或主要进行邻位锂化，而后者仅在α位进行锂化。据报道，有证据表明，对二苯基氮丙啶观察到的α-锂化是邻位-α-位错现象的结果，从而证实了直接的α-去质子化过程。已经考虑了氮丙啶氮孤对的作用：氮丙啶氮的动力学以及络合物诱导的邻近效应似乎是在单苯基和二苯氮丙啶中观察到的区域选择性的原因。结果表明，通过调节反式-1-烷基-2-甲基-3-苯基氮丙啶的锂化反应条件，有可能以高的区域选择性产生α-和/或邻甲硅烷基的氮丙啶，它们可以通过亲电捕获被立体选择性地官能化。通过卤素或锡-锂交换和通过双氘化氮丙啶的去质子化，二苯基氮丙啶的区域选择性邻官能化成为可能。
• Danzer, Wolfgang; Hoefer, Roland; Menzel, Hartmut, Zeitschrift fur Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, 1984, vol. 39, # 2, p. 167 - 179
  作者：Danzer, Wolfgang、Hoefer, Roland、Menzel, Hartmut、Olgemoeller, Bernhard、Beck, Wolfgang

  DOI：——

  日期：——