(2S,3S)-2-allyl-3-phenyl-1-tosylaziridine | 1186384-08-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,3S)-2-allyl-3-phenyl-1-tosylaziridine
• 英文别名: (2S,3S)-1-(4-methylphenyl)sulfonyl-2-phenyl-3-prop-2-enylaziridine
• CAS: 1186384-08-6
• 化学式: C₁₈H₁₉NO₂S
• 分子量: 313.42
• InChiKey: XGTVKGWEGXDEQC-ADUPEVMXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  45.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3S)-2-allyl-3-phenyl-1-tosylaziridine 在 三氟化硼乙醚 、 苄基三乙基氯化铵 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 以92%的产率得到N-((1R,2S)-1-chloro-1-phenylpent-4-en-2-yl)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  BF₃·OEt₂-Mediated Highly Regioselective S_N2-Type Ring-Opening of N-Activated Aziridines and N-Activated Azetidines by Tetraalkylammonium Halides

  摘要：

  A highly regioselective Lewis acid-mediated S(N)2-type ring-opening of N-sulfonylaziridines and azetidines with tetraalkylammonium halides in CH2Cl2 solution to afford 1,2- and 1,3-haloamines in excellent yields is described. An easy diastereoselective route toward substituted chiral N-tosylaziridines has been developed. The mechanism of ring-opening via S(N)2 pathway has been confirmed by the formation of chiral haloamines with excellent er and dr. Chloroamines obtained from 2,3-disubstituted aziridines were converted to the chiral N-tosylamines via radical dehalogenation.

  DOI：

  10.1021/jo902244y
• 作为产物：
  描述：

  N-((1S,2R)-2-hydroxy-1-phenylpent-4-enyl)-4-methylbenzenesulfonamide 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 以96%的产率得到(2S,3S)-2-allyl-3-phenyl-1-tosylaziridine
  参考文献：
  名称：

  BF₃·OEt₂-Mediated Highly Regioselective S_N2-Type Ring-Opening of N-Activated Aziridines and N-Activated Azetidines by Tetraalkylammonium Halides

  摘要：

  A highly regioselective Lewis acid-mediated S(N)2-type ring-opening of N-sulfonylaziridines and azetidines with tetraalkylammonium halides in CH2Cl2 solution to afford 1,2- and 1,3-haloamines in excellent yields is described. An easy diastereoselective route toward substituted chiral N-tosylaziridines has been developed. The mechanism of ring-opening via S(N)2 pathway has been confirmed by the formation of chiral haloamines with excellent er and dr. Chloroamines obtained from 2,3-disubstituted aziridines were converted to the chiral N-tosylamines via radical dehalogenation.

  DOI：

  10.1021/jo902244y

文献信息

• Enantioselective Syntheses of Morpholines and Their Homologues via S_N2-Type Ring Opening of Aziridines and Azetidines with Haloalcohols
  作者：Manas K. Ghorai、Dipti Shukla、Kalpataru Das

  DOI：10.1021/jo901297d

  日期：2009.9.18

  yield and enantioselectivity of a variety of substituted nonracemic morpholines and their homologues is described. The reaction proceeds via an SN2-type ring opening of activated aziridines and azetidines by suitable halogenated alcohols in the presence of Lewis acid followed by base-mediated intramolecular ring closure of the resulting haloalkoxy amine.

  描述了一种高区域和立体选择性策略，用于高产率和对映选择性地合成各种取代的非外消旋吗啉及其同系物。通过S进行反应Ñ在路易斯酸存在下2型开环活性氮丙啶和氮杂环丁烷的通过合适的卤代醇，然后将所得卤代烷氧基胺的碱介导的分子内闭环。
• Stereospecific Synthesis of 2-Iminothiazolidines via Domino Ring-Opening Cyclization of Activated Aziridines with Aryl- and Alkyl Isothiocyanates
  作者：Aditya Bhattacharyya、C. V. Kavitha、Manas K. Ghorai

  DOI：10.1021/acs.joc.6b01551

  日期：2016.8.5

  catalyzed domino ring-opening cyclization of activated aziridines with aryl and alkyl isothiocyanates has been accomplished leading to the formation of a wide variety of highly substituted and functionalized 2-iminothiazolidines with excellent diastereo- and enantiospecificity (de, ee up to >99%). The reaction proceeds via a Lewis acid catalyzed SN2-type ring-opening of the activated aziridine followed by

  用芳基和异硫氰酸烷基酯完成路易斯酸催化活化氮丙啶的多米诺环的开环反应，导致形成各种具有高度非对映体和对映体特异性的高取代和官能化的2-亚氨基噻唑烷（de，ee可达> 99％ ）。反应是通过路易斯酸催化的活化氮丙啶的S N 2型开环进行的，然后以多米诺方式同时进行5- exo-dig环化反应，以极高的收率（高达99％）提供2-iminothiazolidine衍生物。 。
• Syntheses of Chiral β- and γ-Amino Ethers, Morpholines, and Their Homologues via Nucleophilic Ring-Opening of Chiral Activated Aziridines and Azetidines
  作者：Manas K. Ghorai、Dipti Shukla、Aditya Bhattacharyya

  DOI：10.1021/jo300002u

  日期：2012.4.20

  Lewis acid catalyzed quaternary ammonium salt mediated highly regioselective ring-opening of chiral activated aziridines and azetidines with alcohols to nonracemic β- and γ-amino ethers has been developed. The reaction mainly proceeds via an SN2 pathway, and the partial racemization of the starting substrate was effectively controlled by using quaternary ammonium salts. β- and γ-amino ethers are obtained

  已经开发了路易斯酸催化的季铵盐介导的手性活化氮丙啶和氮杂环丁烷与醇的非区域性β-和γ-氨基醚的高度区域选择性开环。该反应主要通过S N 2途径进行，并且通过使用季铵盐有效地控制了起始底物的部分消旋。以高对映体和非对映体特异性（ee最高> 99％，最高99％）获得β-和γ-氨基醚。当将卤代醇用作亲核试剂时，该方法进一步扩展为合成具有高对映体特异性的吗啉及其同系物（ee高达90％）。
• Enantioselective Synthesis of 4,5-Dihydropyrroles via Domino Ring-Opening Cyclization (DROC) of<i>N</i>-Activated Aziridines with Malononitrile
  作者：Manas K. Ghorai、Deo Prakash Tiwari

  DOI：10.1021/jo302815m

  日期：2013.3.15

  An efficient and practical strategy for the synthesis of highly functionalized racemic and non-racemic 4,5-dihydropyrroles via domino ring-opening cyclization (DROC) of activated aziridines with malononitrile in excellent yield and stereoselectivity is described. The reaction serves as a tool for the synthesis of a large variety of substituted 4,5-dihydropyrroles in enantiomerically pure forms.

  描述了一种通过活化的氮丙啶与丙二腈的多米诺开环环化（DROC），以优异的收率和立体选择性合成高度官能化的外消旋和非外消旋4,5-二氢吡咯的有效而实用的策略。该反应用作合成对映体纯形式的多种取代的4，5-二氢吡咯的工具。
• Lewis Acid Catalyzed S_N2-Type Ring Opening of <i>N</i>-Activated Aziridines with Electron-Rich Arenes/Heteroarenes
  作者：Manas K. Ghorai、Deo Prakash Tiwari、Nikita Jain

  DOI：10.1021/jo401028j

  日期：2013.7.19

  An efficient Lewis acid catalyzed S(N)2-type ring opening of substituted aziridines with electron-rich arenes/heteroarenes to provide substituted 2,2-diaryl/heteroarylethylamines in excellent yields and stereoselectivity (er, dr >99:1) is described.