1-(4-nitrophenylsulfonyl)-2-(4-(trifluoromethyl)phenyl)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: 1-(4-nitrophenylsulfonyl)-2-(4-(trifluoromethyl)phenyl)aziridine
• 英文别名: 2-[4-(Trifluoromethyl)phenyl]-1-(4-nitrophenylsulfonyl)aziridine；1-(4-nitrophenyl)sulfonyl-2-[4-(trifluoromethyl)phenyl]aziridine
• 化学式: C₁₅H₁₁F₃N₂O₄S
• 分子量: 372.325
• InChiKey: RHFZCZGXTLERFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  91.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-(4-nitrophenylsulfonyl)-2-(4-(trifluoromethyl)phenyl)aziridine 、 硫代异氰酸苯酯 在 indium(III) triflate 作用下， 以 二氯甲烷 为溶剂， 以29%的产率得到N-(3-((4-nitrophenyl)sulfonyl)-5-(4-(trifluoromethyl)phenyl)thiazolidin-2-ylidene)aniline
  参考文献：
  名称：

  通过包括铁催化的硝基转移和多米诺开环反应（DROC）在内的伸缩反应方便地合成2-亚氨基噻唑烷

  摘要：

  在这项工作中，铁催化的叠氮化（硝烯转移）在一个单一的过程中结合到氮丙啶开环（DROC）中，产生了2-亚氨基噻唑烷，构成了有趣的药物核心。

  DOI：

  10.1002/ejoc.202001379
• 作为产物：
  描述：

  4-硝基苯磺酰胺 在 potassium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 1-(4-nitrophenylsulfonyl)-2-(4-(trifluoromethyl)phenyl)aziridine
  参考文献：
  名称：

  通过包括铁催化的硝基转移和多米诺开环反应（DROC）在内的伸缩反应方便地合成2-亚氨基噻唑烷

  摘要：

  在这项工作中，铁催化的叠氮化（硝烯转移）在一个单一的过程中结合到氮丙啶开环（DROC）中，产生了2-亚氨基噻唑烷，构成了有趣的药物核心。

  DOI：

  10.1002/ejoc.202001379

文献信息

• Imido Transfer from Bis(imido)ruthenium(VI) Porphyrins to Hydrocarbons:  Effect of Imido Substituents, C−H Bond Dissociation Energies, and Ru^VI/V Reduction Potentials
  作者：Sarana Ka-Yan Leung、Wai-Man Tsui、Jie-Sheng Huang、Chi-Ming Che、Jiang-Lin Liang、Nianyong Zhu

  DOI：10.1021/ja0542789

  日期：2005.11.30

  (BDE) of the hydrocarbons. A linear correlation was observed between log k' (k' is the k2 value divided by the number of reactive hydrogens) and BDE and between log k2 and E(1/2)(Ru(VI/V)); the linearity in the former case supports a H-atom abstraction mechanism. The amidation by [Ru(VI)(TMP)(NNs)2] reverses the thermodynamic reactivity order cumene > ethylbenzene/toluene, with k'(tertiary C-H)/k'(secondary

  [Ru(VI)(TMP)(NSO2R)2]（SO2R = Ms、Ts、Bs、Cs、Ns；R = p-C6H4OMe、p-C6H4Me、C6H5、p-C6H4Cl、p-C6H4NO2）和[ Ru(VI)(Por)(NTs)2] (Por = 2,6-Cl2TPP, F20-TPP) 是通过 [Ru(II)(Por)(CO)] 与 PhI=NSO2R 在 CH2Cl2 中的反应制备的。这些配合物表现出可逆的 Ru(VI/V) 对，E(1/2) = -0.41 到 -0.12 V vs Cp2Fe(+/0)，并与苯乙烯、降冰片烯、顺式环辛烯、茚、乙苯进行酰亚胺转移反应，枯烯、9,10-二氢蒽、呫吨、环己烯、甲苯和四氢呋喃以高达 85% 的产率提供氮丙啶或酰胺。298 K 氮丙啶化/酰胺化反应的二级速率常数 (k2) 确定为 (2.6 +/- 0.1) x 10(-5) 至 14.4 +/- 0.6
• A Highly Effective Cobalt Catalyst for Olefin Aziridination with Azides: Hydrogen Bonding Guided Catalyst Design
  作者：Joshua V. Ruppel、Jess E. Jones、Chelsea A. Huff、Rajesh M. Kamble、Ying Chen、X. Peter Zhang

  DOI：10.1021/ol800588p

  日期：2008.5.1

  [Co(P1)], which was designed on the basis of potential hydrogen-bonding interactions in the metal-nitrene intermediate, is a highly active aziridination catalyst with azides. [Co(P1)] can effectively aziridinate various aromatic olefins with arylsulfonyl azides under mild conditions, forming sulfonylated aziridines in excellent yields. The Co-based system enjoys several attributes associated with the relatively low cost of cobalt and the wide accessibility of arylsulfonyl azides. Furthermore, it generates stable dinitrogen as the only byproduct.
• Metal Porphyrin Catalyzed Olefin Aziridination with Sulfonyl Azides
  申请人：Zhang X. Peter

  公开号：US20110112288A1

  公开（公告）日：2011-05-12

  Cobalt(II) complex of P1 [Co(P1)], a new porphyrin that was designed on the basis of potential hydrogen bonding interactions in the metal-nitrene intermediate, is a highly active catalyst for olefin aziridination with azides. The [Co(P1)]-based system can be effectively employed for different combinations of aromatic olefins and arysulfonyl azides, synthesizing various sulfonylated aziridines in excellent yields. Besides its mild catalytic conditions, the Co-catalyzed aziridination process enjoys several attributes associated with the relatively low cost of cobalt and widely accessible arylsulfonyl azides. Furthermore, it generates stable dinitrogen as the only by-product.
• Expedient Synthesis of 2‐Iminothiazolidines via Telescoping Reactions Including Iron‐Catalyzed Nitrene Transfer and Domino Ring‐Opening Cyclization (DROC)
  作者：Guillaume Coin、Oriane Ferrier de Montal、Patrick Dubourdeaux、Jean‐Marc Latour

  DOI：10.1002/ejoc.202001379

  日期：2021.1.22

  In this work, iron‐catalyzed aziridination (nitrene transfer) is combined in a single process to aziridine ring opening (DROC) to produce 2‐iminothiazolidines which constitute interesting cores of pharmaceuticals.

  在这项工作中，铁催化的叠氮化（硝烯转移）在一个单一的过程中结合到氮丙啶开环（DROC）中，产生了2-亚氨基噻唑烷，构成了有趣的药物核心。