cis-2-phenyl-1-tosyl-3-((trimethylsilyl)ethynyl)aziridine

• 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: cis-2-phenyl-1-tosyl-3-((trimethylsilyl)ethynyl)aziridine
• 英文别名: trimethyl-[2-[(2S,3R)-1-(4-methylphenyl)sulfonyl-3-phenylaziridin-2-yl]ethynyl]silane
• 化学式: C₂₀H₂₃NO₂SSi
• 分子量: 369.56
• InChiKey: IVZPKNIOYJYEIR-MCOCGALXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.99
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  cis-2-phenyl-1-tosyl-3-((trimethylsilyl)ethynyl)aziridine 在 三苯基膦氯金 、 silver trifluoromethanesulfonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 12.0h， 以70%的产率得到2-phenyl-1-tosyl-1H-pyrrole
  参考文献：
  名称：

  通过金催化的乙炔基氮丙啶的环异构化，轻松，区域选择性地合成2,5-二取代的吡咯

  摘要：

  乙炔基氮丙啶的金催化的环异构化反应以高收率提供了2,5-二取代的吡咯。质子物种的存在加快了反应速度并提高了吡咯产物的产率。

  DOI：

  10.1016/j.tetlet.2009.05.091
• 作为产物：
  描述：

  3-溴-1-三甲基硅基-1-丙炔 在 caesium carbonate 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 生成 cis-2-phenyl-1-tosyl-3-((trimethylsilyl)ethynyl)aziridine
  参考文献：
  名称：

  动力学控制的自由基加成/消除级联：从炔基氮丙啶到氟化的异戊烯。

  摘要：

  开发了动力学控制的自由基加成/消除反应，该反应产生了氟化烯。该策略提供了在可见光照射下从容易获得的氟代烷基卤化物和炔基氮丙啶类化合物轻松合成各种三氟甲基，二氟亚甲基和全氟烷基官能化的烯基的途径。该自由基时钟类型反应的密度泛函理论计算显示，动力学控制的CN键断裂可克服热力学控制的CC键断裂。

  DOI：

  10.1021/acs.orglett.0c00622

文献信息

• Highly Stereoselective Ylide Aziridination of <i>N</i>-Sulfonylimines with Sulfonium Propargylides:  A Simple Way To Synthesize Scalemic Acetylenylaziridines
  作者：An-Hu Li、Yong-Gui Zhou、Li-Xin Dai、Xue-Long Hou、Li-Jun Xia、Lin

  DOI：10.1021/jo9800964

  日期：1998.6.1

  Under phase-transfer or low-temperature conditions, the ylide generated from diphenylsulfonium salt 2 readily reacts with N-sulfonylimines 1 to give acetylenylaziridines in excellent yields, but low to moderate cis/trans selectivity. When using n-BuLi as the base to generate the ylide at low termperature, product 3 with an intact silyl protecting group is obtained. t-BuOK, however, leads to desilylation product 4. With Cs2CO3 as the base, dimethylsulfonium salts 6, 21, and 22 show much better cis/trans selectivity (>98:2) than diphenylsulfonium salt 2. The asymmetric version of the above aziridination reaction using camphor-derived sulfonium salts 12-14 and 20 gives chiral aziridines with ee values up to 85%. Both (2R,3S)-(-)-3 and (2S,3R)-(+)-3 can be prepared from 12/20 or 13/14, respectively. Ylides produced from telluronium salt 7 failed to react with imine la at room temperature, but the reaction succeeded at low temperature. Arsonium ylides from 8 cannot react with N-sulfonylimines under both sets of conditions.
• Synthesis of substituted 3-iodopyrroles by cycloisomerization of propargylic aziridines with iodine
  作者：Masahiro Yoshida、Salina Easmin、Mohammad Al-Amin、Yuuki Hirai、Kozo Shishido

  DOI：10.1016/j.tet.2011.03.015

  日期：2011.5

  The electrophilic cyclizations of N-substituted propargylic aziridines are described. 3-lodopyrroles having a variety of substituents at the 2- and 3-positions were synthesized by reacting propargylic aziridines with iodine. Whereas N-tosyl-substituted substrates require a platinum catalyst to promote the reaction, the iodine-promoted cycloisomerizations proceed when N-benzyl-substituted substrates are employed. (C) 2011 Elsevier Ltd. All rights reserved.
• A new stereoselective access to N-benzyl trans-propargylic aziridines
  作者：Fabrice Chemla、Virginie Hebbe、Jean F Normant

  DOI：10.1016/s0040-4039(99)01688-3

  日期：1999.11

  The metallation of 3-trimethylsilyl-1-chloroprop-2-yne and the subsequent reaction with N-benzyl imines affords stereospecifically trans propargylic aziridines with good to excellent yields. (C) 1999 Elsevier Science Ltd. All rights reserved.
• A facile and regioselective synthesis of 2,5-disubstituted pyrroles via gold-catalyzed cycloisomerization of acetylenylaziridines
  作者：Dong-Dong Chen、Xue-Long Hou、Li-Xin Dai

  DOI：10.1016/j.tetlet.2009.05.091

  日期：2009.12

  Gold-catalyzed cycloisomerization reaction of acetylenylaziridines provides 2,5-disubstituted pyrroles in high yields. The presence of protic species accelerates the reaction rate and improves the yields of pyrrole products.

  乙炔基氮丙啶的金催化的环异构化反应以高收率提供了2,5-二取代的吡咯。质子物种的存在加快了反应速度并提高了吡咯产物的产率。
• Kinetically Controlled Radical Addition/Elimination Cascade: From Alkynyl Aziridine to Fluorinated Allenes
  作者：Tingting Song、Lei Zhu、Haoyu Li、Chen-Ho Tung、Yu Lan、Zhenghu Xu

  DOI：10.1021/acs.orglett.0c00622

  日期：2020.3.20

  A kinetically controlled radical addition/elimination reaction generating fluorinated allenes was developed. This strategy offers a route to a facile synthesis of diverse trifluoromethyl, difluoromethylene, and perfluoroalkyl functionalized allenes from readily available fluoroalkyl halides and alkynyl aziridines under visible-light irradiation. Density functional theory calculation of this radical

  开发了动力学控制的自由基加成/消除反应，该反应产生了氟化烯。该策略提供了在可见光照射下从容易获得的氟代烷基卤化物和炔基氮丙啶类化合物轻松合成各种三氟甲基，二氟亚甲基和全氟烷基官能化的烯基的途径。该自由基时钟类型反应的密度泛函理论计算显示，动力学控制的CN键断裂可克服热力学控制的CC键断裂。