trans-2-phenyl-3-n-propyl-N-tosylaziridine

• 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: trans-2-phenyl-3-n-propyl-N-tosylaziridine
• 英文别名: (2S,3S)-1-(4-methylphenyl)sulfonyl-2-phenyl-3-propylaziridine
• 化学式: C₁₈H₂₁NO₂S
• 分子量: 315.436
• InChiKey: GLLGOJFJSRADQZ-ADUPEVMXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  trans-2-phenyl-3-n-propyl-N-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95%的产率得到N-((1R,2S)-1-chloro-1-phenylpentan-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-(2-hydroxy-1-phenylpentyl)-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98%的产率得到trans-2-phenyl-3-n-propyl-N-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

• A Synthetic Route to Chiral Tetrahydropyrroloindoles via Ring Opening of Activated Aziridines with 2-Bromoindoles Followed by Copper-Catalyzed C–N Cyclization
  作者：Masthanvali Sayyad、Abhijit Mal、Imtiyaz Ahmad Wani、Manas K. Ghorai

  DOI：10.1021/acs.joc.6b01049

  日期：2016.8.5

  A new synthetic route to nonracemic tetrahydropyrrolo[2,3-b]indoles has been developed via SN2-type ring opening of enantiopure N-activated aziridines with 2-bromoindoles followed by copper-catalyzed C–N cyclization. A series of N-activated aziridines and 2-bromoindole derivatives with different substitution patterns were studied to afford the corresponding tetrahydropyrrolo[2,3-b]indoles in good yields

  通过用2-溴吲哚将对映纯N活化的氮丙啶的S N 2型开环，然后进行铜催化的CN环化，已开发出一种新的合成非外消旋四氢吡咯并[2,3- b ]吲哚的途径。研究了一系列具有不同取代模式的N活化氮丙啶和2-溴吲哚衍生物，从而以良好的收率和优异的ee（高达99％）提供了相应的四氢吡咯并[2,3- b ]吲哚。高度取代的四氢吡咯并[2，3- b ]吲哚由对映体纯的反式-二取代的氮丙啶合成为单个立体异构体（de，ee> 99％）。
• Novel Asymmetric and Stereospecific Aziridination of Alkenes with a Chiral Nitridomanganese Complex
  作者：Satoshi Minakata、Takeya Ando、Masaaki Nishimura、Ilhyong Ryu、Mitsuo Komatsu

  DOI：10.1002/(sici)1521-3773(19981231)37:24<3392::aid-anie3392>3.0.co;2-g

  日期：1998.12.31

  necessary to obtain high enantioselectivities in the asymmetric aziridination of styrene derivatives through transfer of a nitrogen atom from chiral, toluenesulfonic anhydride activated nitridomanganese complex 1 [Eq. (a)]. Remarkably, high stereospecificity was observed in all the aziridinations of trans- and cis-1,2-disubstituted alkenes. R1 =H, Me, nPr, iPr; R2 =H, Me; Ts=p-toluenesulfonyl.

  通过从手性甲苯磺酸酐活化的硝基锰配合物1转移氮原子来获得苯乙烯衍生物的不对称叠氮化中的高对映选择性，需要添加吡啶N-氧化物。（一种）]。显着地，在反式和顺式1,2-二取代的烯烃的所有叠氮基中观察到高立体定向性。R 1＝ H，Me，nPr，iPr；R 2＝ H，Me；Ts ＝对甲苯磺酰基。
• 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。 。
• A Synthetic Route to Chiral Dihydrobenzothiazines through Ring Opening of Activated Aziridines with 2-Halothiophenols/Copper-Powder-Mediated C−N Cyclization
  作者：Manas K. Ghorai、Masthanvali Sayyad、Yerramsetti Nanaji、Sourita Jana

  DOI：10.1002/asia.201500153

  日期：2015.7

  A simple protocol for the synthesis of dihydrobenzothiazines through regio‐ and stereoselective SN2‐type ring opening of N‐tosylaziridines with sulfur nucleophiles followed by copper‐powder‐mediated intramolecular C−N cyclization in excellent yields (up to 95 %) with high diastereo‐ and enantioselectivity (up to >99 %) is reported.

  一种简单的方案，可通过硫磺亲核试剂对N-甲苯磺酰氮丙啶的区域和立体选择性S N 2型开环，然后铜粉介导的分子内C-N环化，以高收率（高达95％）合成二氢苯并噻嗪据报道非对映选择性和对映选择性（最高> 99％）。
• 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％）。