3-pyridyl nonaflate | 32848-20-7

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代烷
• 英文名称: 3-pyridyl nonaflate
• 英文别名: nonafluoro-butane-1-sulfonic acid pyridin-3-yl ester；Perfluorbutansulfonsaeure-3-pyridylester；3-Perfluorbutylsulfonyloxy-pyridin；1-Butanesulfonic acid, 1,1,2,2,3,3,4,4,4-nonafluoro-, 3-pyridinyl ester；pyridin-3-yl 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate
• CAS: 32848-20-7
• 化学式: C₉H₄F₉NO₃S
• 分子量: 377.187
• InChiKey: LMDWAFUQVIROQT-UHFFFAOYSA-N

物化性质

• 沸点：
  282.1±40.0 °C(Predicted)
• 密度：
  1.665±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  二苯甲酮亚胺 、 3-pyridyl nonaflate 在 tris(dibenzylideneacetone)dipalladium (0) 、 7-甲基-1,5,7-三氮杂二环[4.4.0]癸-5-烯 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以99%的产率得到N-(二苯基亚甲基)吡啶-3-胺
  参考文献：
  名称：

  通过使用微波辐射和可溶性有机胺碱加快钯催化芳基壬酸酯的胺化

  摘要：

  使用可溶性胺碱DBU（1,8-二氮杂双环[5.4.0]十一碳-7-烯）或MTBD（7-甲基）与芳基/杂芳基壬酸酯和胺进行微波辅助的钯催化的CN键形成反应-1,5,7三氮杂双环[4.4.0]癸-5-烯）和配体（1 - 3导致良好的在短的反应时间的芳基胺的产率优异（71-99％）（1-45分钟）） 。

  DOI：

  10.1021/jo052131u
• 作为产物：
  描述：

  3-羟基吡啶 、 全氟丁基磺酰氟 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 以91%的产率得到3-pyridyl nonaflate
  参考文献：
  名称：

  A General Method for Palladium-Catalyzed Reactions of Primary Sulfonamides with Aryl Nonaflates

  摘要：

  A general method for Pd-catalyzed sulfonamidation of aryl nonafluorobutanesulfonates (aryl nonaflates) is described. A biaryl phosphine ligand, t-BuXPhos, formed the most active catalyst, and K3PO4 in tert-amyl alcohol was found to be the optimal base solvent combination for the reaction. The reaction conditions were tolerant of various functional groups such as cyano, nitro, ester, aldehyde, ketone, chloride, carbamate, and phenol. Heterocyclic aryl nonaflates were found to be suitable coupling partners. High yields of the coupled products were obtained from the reactions between inherently disfavored substrates such as electron-rich nonaflates and electron-poor sulfonamides. Kinetic data suggest reductive elimination to be the rate-limiting step for the reaction. The only limitation of this methodology that we have identified is the inability of 2,6-disubstituted aryl nonaflates to efficiently participate in the reaction.

  DOI：

  10.1021/jo200443u

文献信息

• Mo(CO)6 as a Solid CO Source in the Synthesis of Aryl/Heteroaryl Weinreb Amides under Microwave-Enhanced Condition
  作者：Raghu Ningegowda、Savitha Bhaskaran、Ayyiliath M. Sajith、Chandrashekar Aswathanarayanappa、M. Syed Ali Padusha、Nanjunda Swamy Shivananju、Babu Shubha Priya

  DOI：10.1071/ch16213

  日期：——

  The facile transformation of aryl/heteroaryl nonaflates into corresponding amides via Pd-catalyzed aminocarbonylation using Mo(CO)6 as a solid CO source under microwave-enhanced condition is reported. The method was found to be tolerant with respect to a diverse range of electronically biased aryl/heteroaryl nonaflates, and exceptional yields were obtained. The optimized protocol was further extended

  报道了在微波增强条件下，使用Mo（CO）6作为固体CO源，通过Pd催化的氨基羰基化，将芳基/杂芳基壬二酸芳酯轻松转化为相应的酰胺。发现该方法对于多种电子偏置的芳基/杂芳基壬二酸酯的耐受性，并且获得了优异的产率。优化的方案进一步扩展到多种胺。
• Palladium — Catalyzed Reactions, 1 Palladium‐Catalyzed Enantioselective Hydrophenylation and Hydrohetarylation of Bicyclo[2.2.1]Hept‐2‐ene: Influence of the Chiral Ligand, the Leaving Group, and the Solvent
  作者：Jan Christoph Namyslo、Dieter E. Kaufmann

  DOI：10.1002/cber.19971300924

  日期：1997.9

  henylphosphane 7 as ligands in the Pd-catalyzed Heck-type hydroarylation of norbornene (1) with phenyl 2 and various hetaryl derivaties 3–5 leads exclusively to the formation of exo-2(het)arylnorbornanes 6 with asymmetric inductions of up to 86.4% ee. In addition to an investigation into the effects of different chiral ligands, a systematic study has been made of the influence of various (het)aryl

  使用光学活性的联芳基bisphosphanes的10 - 12，一个diphenylphosphanylphenyloxazoline 8，和一个（β-N-磺酰氨基甲基）bisdiphenylphosphane 7，如降冰片烯（的Pd催化的Heck型hydroarylation配体1与苯基）2和各种杂芳基衍生品3 – 5仅导致exo-2（het）arylnorbornaneanes的形成6具有高达86.4％ee的不对称感应。除了研究不同手性配体的作用外，还对各种（杂）芳基化合物，离去基团和溶剂对这种还原性芳基化反应的化学和光学收率的影响进行了系统的研究。
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: F: PerFHalOrg.2, 1.3.4, page 137 - 166
  作者：

  DOI：——

  日期：——
• Niederpruem, H.; Voss, P.; Beyl, V., Liebigs Annalen der Chemie
  作者：Niederpruem, H.、Voss, P.、Beyl, V.

  DOI：——

  日期：——
• Expedited Palladium-Catalyzed Amination of Aryl Nonaflates through the Use of Microwave-Irradiation and Soluble Organic Amine Bases
  作者：Rachel E. Tundel、Kevin W. Anderson、Stephen L. Buchwald

  DOI：10.1021/jo052131u

  日期：2006.1.1

  Microwave-assisted, palladium-catalyzed C−N bond-forming reactions with aryl/heteroaryl nonaflates and amines using the soluble amine bases DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) or MTBD (7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene) and ligands (1−3) resulted in good to excellent yields (71−99%) of arylamines in short reaction times (1−45 min).

  使用可溶性胺碱DBU（1,8-二氮杂双环[5.4.0]十一碳-7-烯）或MTBD（7-甲基）与芳基/杂芳基壬酸酯和胺进行微波辅助的钯催化的CN键形成反应-1,5,7三氮杂双环[4.4.0]癸-5-烯）和配体（1 - 3导致良好的在短的反应时间的芳基胺的产率优异（71-99％）（1-45分钟）） 。