(2S,3S)-2-butyl-3-phenyl-1-tosylaziridine | 1202798-69-3

• 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-butyl-3-phenyl-1-tosylaziridine
• 英文别名: (2S,3S)-2-butyl-1-(4-methylphenyl)sulfonyl-3-phenylaziridine
• CAS: 1202798-69-3
• 化学式: C₁₉H₂₃NO₂S
• 分子量: 329.463
• InChiKey: BIHPEFFCPNQKEE-NFBCFJMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 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-butyl-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98%的产率得到N-((1R,2S)-1-chloro-1-phenylhexan-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-phenylhexyl)-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95%的产率得到(2S,3S)-2-butyl-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

• 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％）。
• Ring Opening/C–N Cyclization of Activated Aziridines with Carbon Nucleophiles: Highly Diastereo- and Enantioselective Synthesis of Tetrahydroquinolines
  作者：Manas K. Ghorai、Y. Nanaji、A. K. Yadav

  DOI：10.1021/ol2016077

  日期：2011.8.19

  A simple strategy for the synthesis of substituted tetrahydroquinolines through regio- and stereoselective ring opening of N-tosyl aziridines with carbon nucleophiles generated from 2-(bromoaryl)acetonitriles followed by palladium-catalyzed intramolecular C–N cyclization is reported in excellent yields (up to >99%) and stereoselectivity (ee and de up to >99%).

  据报道，通过N-甲苯磺酰基氮丙啶的区域和立体选择性开环与由2-（溴芳基）乙腈生成的碳亲核试剂，然后由钯催化的分子内C-N环化，合成取代的四氢喹啉的简单策略，收率很高（高达> 99％）和立体选择性（ee和de高达> 99％）。
• BF₃·OEt₂-Mediated Highly Regioselective S_N2-Type Ring-Opening of <i>N</i>-Activated Aziridines and <i>N</i>-Activated Azetidines by Tetraalkylammonium Halides
  作者：Manas K. Ghorai、Amit Kumar、Deo Prakash Tiwari

  DOI：10.1021/jo902244y

  日期：2010.1.1

  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.