1-naphthyl perfluorobutanesulfonate | 32848-17-2

• 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: 1-naphthyl perfluorobutanesulfonate
• 英文别名: 1-naphthalenyl nonaflate；1-naphthyl nonaflate；Perfluorbutylsulfonsaeure-α-naphthylester；Naphthalen-1-yl 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate
• CAS: 32848-17-2
• 化学式: C₁₄H₇F₉O₃S
• 分子量: 426.259
• InChiKey: ZILPWBSTMHSUEE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  1-naphthyl perfluorobutanesulfonate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以92%的产率得到萘
  参考文献：
  名称：

  Hydrierende Spaltung phenolischer und enolischer Perfluoroalkansulfonate

  摘要：

  DOI：

  10.1055/s-1984-30873
• 作为产物：
  描述：

  全氟丁基磺酰氟 、 萘酚 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 以92 %的产率得到1-naphthyl perfluorobutanesulfonate
  参考文献：
  名称：

  多氟苯甲酸锌 (II) 与芳基溴和九氟甲磺酸酯的温和脱羧交叉偶联：获得多氟联芳基化合物

  摘要：

  我们开发了一种钯催化的多氟苯甲酸锌脱羧交叉偶联方法，用作原位生产锌试剂的前体，与芳基溴和九氟磺酸盐发生反应，为多氟联芳基化合物的合成提供了一条温和有效的途径。该协议具有广泛的底物范围和出色的功能耐受性。此外，药物、生物活性分子和农药的直接后期修饰证明了这种方法的多功能性，表明其在药物发现中的潜在意义。

  DOI：

  10.1021/acs.orglett.3c03730

文献信息

• A New, Efficient and Stereoselective Synthesis of Tricyclic and Tetracyclic Compounds by Samarium Diiodide Induced Cyclisations of Naphthyl-Substituted Arylketones—An Easy Access to Steroid-Like Skeletons
  作者：Francesca Aulenta、Mathias Berndt、Irene Brüdgam、Hans Hartl、Sebastian Sörgel、Hans-Ulrich Reißig

  DOI：10.1002/chem.200700057

  日期：2007.7.16

  we present the application of samarium diiodide induced cyclisations of naphthyl-substituted ketones towards an easy and stereoselective access to tri- and tetracyclic-functionalised compounds. Typical naphthalene derivatives were studied to investigate the scope and limitations of this novel cyclisation process. The model substrates studied demonstrate that the samarium ketyl cyclisations are essentially

  在本报告中，我们介绍了由二碘化sa诱导的萘基取代的酮的环化，其对三环和四环官能化化合物的容易和立体选择。对典型的萘衍生物进行了研究，以研究这种新型环化方法的范围和局限性。所研究的模型底物表明，酮基环化基本上仅限于六元环的形成。这些反应的非对映选择性受到烷基侧链与萘核的连接的强烈影响。γ-萘-1-基取代的酮提供环化产物，例如17或22-26，为单一非对映异构体，相反，γ-萘-2-基取代的前体可得到非对映异构体的混合物-如模型化合物10转化为三环产物18a / 18b或环己酮衍生物33转化为四环非对映异构体34a / 34b所证明。作为酮基前体的环状酮提供了类固醇状的四环骨架。然而，由于环B / C和C / D的顺式/顺式融合，这些产物具有“不自然的”碗状形状。X射线分析已鉴定出几种环化产物，不仅证明了结构，而且证明了相对构型和优选构象。类固醇类似物23经历随后的转化，这表明此类化合物的类苯乙
• 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。
• 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。
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: F: PerFHalOrg.2, 1.3.4, page 137 - 166
  作者：

  DOI：——

  日期：——
• A General Method for Palladium-Catalyzed Reactions of Primary Sulfonamides with Aryl Nonaflates
  作者：Shashank Shekhar、Travis B. Dunn、Brian J. Kotecki、Donna K. Montavon、Steven C. Cullen

  DOI：10.1021/jo200443u

  日期：2011.6.3

  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.