(+/-)-2-(pentafluorophenyl)-1-tosylaziridine | 148961-15-3

• 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: (+/-)-2-(pentafluorophenyl)-1-tosylaziridine
• 英文别名: 1-(4-Methylphenyl)sulfonyl-2-(2,3,4,5,6-pentafluorophenyl)aziridine
• CAS: 148961-15-3
• 化学式: C₁₅H₁₀F₅NO₂S
• 分子量: 363.308
• InChiKey: DAOQTEHZVPRTHZ-UHFFFAOYSA-N

物化性质

• 沸点：
  368.6±52.0 °C(Predicted)
• 密度：
  1.558±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 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：
  45.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (+/-)-2-(pentafluorophenyl)-1-tosylaziridine 、 烯丙基溴化镁 以 四氢呋喃 、 乙醚 为溶剂， 反应 3.0h， 以93%的产率得到(+/-)-N-<2-(pentafluorophenyl)pent-4-enyl>toluene-p-sulfonamide
  参考文献：
  名称：

  Toshimitsu, Akio; Abe, Hideyuki; Hirosawa, Chitaru, Journal of the Chemical Society. Perkin transactions I, 1994, # 23, p. 3465 - 3472

  摘要：

  DOI：
• 作为产物：
  描述：

  对甲苯磺酰胺 在 C₃₆H₄₃BCuN₄P 、 potassium hydroxide 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 25.5h， 生成 (+/-)-2-(pentafluorophenyl)-1-tosylaziridine
  参考文献：
  名称：

  双(吡唑基)硼酸铜(I)配合物催化烯烃的选择性环丙烷化/氮丙啶化

  摘要：

  具有分子内 C−H···Cu 弱相互作用作为“开关”的双（吡唑基）硼酸铜（I）络合物催化剂已应用于催化卡宾/氮烯转移和 C=C 键的加成。催化环丙烷化/氮丙啶化反应表现出广泛的底物范围、高产率和选择性。

  DOI：

  10.1002/ejoc.202200790

文献信息

• A New Approach to Non-Coordinating Anions: Lewis Acid Enhancement of Porphyrin Metal Centers in a Zwitterionic Metal–Organic Framework
  作者：Jacob A. Johnson、Brenna M. Petersen、Attila Kormos、Elena Echeverría、Yu-Sheng Chen、Jian Zhang

  DOI：10.1021/jacs.6b05626

  日期：2016.8.17

  cationic metal center. We demonstrate the enhanced Lewis acidity of Mn(III)- and Fe(III)-porphyrins in the zwitterionic MOFs in three representative electrocyclization reactions: [2 + 1] cycloisomerization of enynes, [3 + 2] cycloaddition of aziridines and alkenes, and [4 + 2] hetero-Diels-Alder cycloaddition of aldehydes with dienes. This work paves a new way to design functional MOFs for tunable chemical

  我们描述了一种使用两性离子金属有机框架 (MOF) 生成非配位阴离子的新策略。通过将阴离子无机二级结构单元 (SBU) ([In(CO2)4](-)) 与基于阳离子金属卟啉的有机连接体组装在一起，我们制备了两性离子 MOF，其中完全的内部电荷分离有效地防止了抗衡阴离子的潜在结合到阳离子金属中心。我们在三个代表性的电环化反应中证明了两性离子 MOF 中 Mn(III)-和 Fe(III)-卟啉的路易斯酸度增强：烯炔的 [2 + 1] 环化异构化，氮丙啶和烯烃的 [3 + 2] 环加成，以及[4 + 2] 醛与二烯的杂-Diels-Alder 环加成反应。这项工作为设计用于可调化学催化的功能性 MOF 铺平了道路。
• Cobalt-based catalysts for the cyclization of alkenes
  申请人：Zhang Peter X.

  公开号：US20060030718A1

  公开（公告）日：2006-02-09

  Metal-ligand complexes, including cobalt-ligand complexes, such as a cobalt-porphyrin complex, and their use as catalysts in the cyclization of alkenes.

  金属配合物，包括钴配体配合物，如钴卟啉配合物，以及它们在烯烃环化反应中作为催化剂的使用。
• Syntheses of a Novel Fluorinated Trisphosphinoborate Ligand and Its Copper and Silver Complexes. Catalytic Activity toward Nitrene Transfer Reactions
  作者：Ismael Arenas、M. Ángeles Fuentes、Eleuterio Álvarez、Yolanda Díaz、Ana Caballero、Sergio Castillón、Pedro J. Pérez

  DOI：10.1021/ic4028223

  日期：2014.4.21

  A novel fluorinated ligand, the anionic PhB(CH2P(p-CF3C6H4)(2))(3) (PhBP3 (p-CF3Ph)); has been synthesized and characterized, as well as its corresponding thallium, copper, and silver derivatives. The presence of fluorine atoms in the ligand structure induced the desired effect of enhancing electrophilic character at the metal center, without promoting substantial changes in the ligand skeleton compared with the parent ligand PhB(CH2PPh2)(3) - (PhBP3). Olefin aziridination and C-H amidation reactions have been induced with those complexes as catalyst precursors. The copper derivative catalyzed the olefin aziridination of an array of olefins bearing either electron-donating or electron-withdrawing groups. The silver analogue was found to promote the C-H amidation of a series of substrates in moderate to high yields.
• Generation and Ring Opening of Aziridines in Telescoped Continuous Flow Processes
  作者：Nathanael Hsueh、Guy J. Clarkson、Michael Shipman

  DOI：10.1021/acs.orglett.5b01777

  日期：2015.7.17

  A simple method for the preparation of a variety of N-sulfonyl aziridines (10 examples) from 1,2-amino alcohols under continuous flow conditions is described. Using flow based methods, the aziridines can be further ring opened with oxygen, carbon, and halide nucleophiles or ring expanded to imidazolines by Lewis acid promoted reaction with nitriles. Telescoping the aziridine generation and ring opening steps together in a microfluidic reactor allows the chemistry to be undertaken with limited exposure to the potentially hazardous aziridine intermediates.
• Cobalt-Catalyzed Efficient Aziridination of Alkenes
  作者：Guang-Yao Gao、Jeremiah D. Harden、X. Peter Zhang

  DOI：10.1021/ol050896i

  日期：2005.7.1

  Cobalt porphyrins are capable of catalyzing the azirldination of alkenes with bromamine-T as the nitrene source. Among cobalt complexes of different porphyrins, Co(TDCIPP) is an effective catalyst that can aziridinate a wide variety of alkenes. The catalytic system can operate at room temperature in a one-pot fashion with alkenes as limiting reagents, forming the desired N-sulfonylated aziridine derivatives in high to excellent yields with NaBr as the byproduct.