para-nitrophenyl perfluorobutanesulfonate | 32848-23-0

• 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: para-nitrophenyl perfluorobutanesulfonate
• 英文别名: 4-nitrophenyl nonaflate；4-nitrophenyl nonafluorobutanesulfonate；Perfluorbutylsulfonsaeure-4-nitrophenylester；Nonafluoro-1-butanesulfonic acid 4-nitrophenyl ester；(4-nitrophenyl) 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate
• CAS: 32848-23-0
• 化学式: C₁₀H₄F₉NO₅S
• 分子量: 421.197
• InChiKey: BVXUHVNQOSYNMF-UHFFFAOYSA-N

物化性质

• 熔点：
  70 °C
• 沸点：
  343.7±42.0 °C(Predicted)
• 密度：
  1.718±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  97.6
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  para-nitrophenyl perfluorobutanesulfonate 在 potassium fluoride 作用下， 以 乙腈 为溶剂， 以93%的产率得到全氟丁基磺酰氟
  参考文献：
  名称：

  [EN] METHOD FOR RECOVERING SULFONIC ESTERS OR SULFONYL HALIDES FROM SALTS OF SULFONIC ACIDS
  [FR] PROCÉDÉ DE RÉCUPÉRATION D'ESTERS SULFONIQUES OU D'HALOGÉNURES DE SULFONYLE À PARTIR DE SELS D'ACIDES SULFONIQUES

  摘要：

  本文公开了一种从磺酸盐中获得氟磺酸酯或卤代物的方法。该方法特别适用于从通过磺酸醇酯与亲核化合物反应获得的反应混合物中回收废弃磺酸盐。

  公开号：

  WO2017016943A1
• 作为产物：
  描述：

  phenyl nonaflate 在 硫酸 、 硝酸 作用下， 反应 4.0h， 以90%的产率得到para-nitrophenyl perfluorobutanesulfonate
  参考文献：
  名称：

  Aryl fluoroalkanesulfonate chemistry. A new approach to labelled arene elaboration

  摘要：

  DOI：

  10.1002/jlcr.1181

文献信息

• Oxaza Adamantyl Cannabinoids. A New Class of Cannabinoid Receptor Probes
  作者：David Le Goanvic、Marcus A. Tius

  DOI：10.1021/jo061352c

  日期：2006.9.1

  described starting from phloroglucinol. Straightforward manipulations of the aromatic ring lead to a bromononaflate that is a benzyne precursor and that serves as a common intermediate for the synthesis of diverse C3-substituted tricyclic cannabinoids. Generation of the benzyne in the presence of an oxaza adamantyl amide anion results in efficient and regiospecific addition to C3 of the aromatic ring. This

  已经描述了从间苯三酚开始制备C3氧杂氮杂金刚烷基大麻素的方法。芳香环的直接操作会生成溴苯磺酸盐，它是苯炔的前体，并用作合成各种C3取代的三环大麻素的常用中间体。在氧杂氮杂金刚烷基酰胺阴离子的存在下生成苯并炔导致向芳族环的C 3有效且区域专一地加成。这代表了合成具有修饰的芳香附属物的经典三环大麻素的有吸引力的策略。已制备的恶草金刚烷基大麻素代表了CB1和CB2受体的新型配体。
• 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。
• A high throughput synthesis of aryl triflate and aryl nonaflate promoted by a polymer supported base (PTBD)
  作者：Sabine Boisnard、Jaqueline Chastanet、Jieping Zhu

  DOI：10.1016/s0040-4039(99)01529-4

  日期：1999.10

  A rapid synthesis of aryl nonaflate was developed using 4-nitrophenyl triflate and 4-nitrophenyl nonaflate as perfluoroalkanesulfonyl transfer reagents in combination with a polymer supported base (PTBD). Simple filtration of the reaction mixture gave the desired products in high chemical yields and purity. The unique role of PTBD as a base and side product scavenger was demonstrated.

  使用4-硝基苯基三氟甲磺酸酯和4-硝基苯基九氟乙烯酸酯作为全氟烷烃磺酰基转移试剂，并与聚合物负载的碱（PTBD）结合，可以快速合成芳基壬酸酯。简单过滤反应混合物，以高化学产率和纯度得到所需产物。证明了PTBD作为基础和副产品清除剂的独特作用。
• Fluorinated Alkanesulfonic Acid Esters and Amides and Processes for Making and Using the Same
  申请人：Rostovtsev Vsevolod

  公开号：US20090137831A1

  公开（公告）日：2009-05-28

  The invention provides novel aryl and aliphatic esters of fluorinated alkanesulfonic acids. The invention also provides novel fluorinated alkanesulfonamides and a process to make the same. The invention also provides a process for the arylation of an amine by contacting the amine with an aryl ester of a fluorinated alkanesulfonic acid.

  本发明提供了新型的芳基和脂肪族酯化的氟代烷磺酸。本发明还提供了新型的氟代烷磺酰胺及其制备方法。本发明还提供了一种通过将胺与氟代烷磺酸的芳基酯接触而进行芳基化的方法。
• Synthesis of multisubstituted pyrroles by ligand-controlled site-selective arylation and their transformation into multiarylated pyrrolines and pyrrolidines
  作者：Miyuki Yamaguchi、Sakiko Fujiwara、Yukiko Mori、Hideyuki Konishi、Kei Manabe

  DOI：10.1016/j.tet.2022.132962

  日期：2022.9

  Multisubstituted pyrroles were prepared by Pd-catalyzed site-selective arylation of 2,5-disubstituted 1H-pyrroles with aryl chlorides, triflates, or nonaflates. Site-selectivity of the reaction was controlled using appropriate ligands, and 2,2,5-trisubstituted 2H-pyrroles were synthesized via dearomative C2-arylation. Moreover, 2,3,5-trisubstituted 1H-pyrroles were successfully fabricated by direct

  多取代的吡咯是通过 Pd 催化的 2,5-二取代的 1 H-吡咯与芳基氯化物、三氟甲磺酸酯或九氟甲磺酸酯的位点选择性芳基化来制备的。使用适当的配体控制反应的位点选择性，并通过脱芳烃 C2-芳基化合成 2,2,5-三取代的 2 H-吡咯。此外，通过直接C3-芳基化成功制备了2,3,5-三取代的1 H-吡咯。这些芳基化可应用于带有芳基氯部分的药物。此外，2,2,5-三芳基-2 H-吡咯被转化为多芳基化吡咯啉和吡咯烷，可用于合成和药物化学。