1-[双(三氟甲基磺酰基)甲基]萘 | 130875-42-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 1-[双(三氟甲基磺酰基)甲基]萘
• 英文名称: (1-naphthyl)bis(triflyl)methane
• 英文别名: bis(trifluoromethylsulfonyl)-1-naphthylmethane；Naphthalene, 1-[bis[(trifluoromethyl)sulfonyl]methyl]-；1-[bis(trifluoromethylsulfonyl)methyl]naphthalene
• CAS: 130875-42-2
• 化学式: C₁₃H₈F₆O₄S₂
• 分子量: 406.327
• InChiKey: BZQAOASUJNTSGD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  85
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  1-溴甲基萘 在 丙腈 作用下， 生成 1-[双(三氟甲基磺酰基)甲基]萘
  参考文献：
  名称：

  Facile Synthesis of Aryl- and Alkyl-bis(trifluoromethylsulfonyl)methanes

  摘要：

  通过将相应的苄基卤化物与三氟甲烷亚硫酸钠反应，然后再与三氟甲磺酸酐反应，合成了多种芳香基双(三氟甲磺酰)甲烷 (1)。此外，当1中的芳基是五氟苯基时，芳基的亲核性对位取代反应可以通过烷基锂和烷氧化钠实现。这一反应对于设计新型布朗斯特酸具有实用价值。

  DOI：

  10.1246/bcsj.78.1401

文献信息

• Polymer-supported arylbis(perfluoroalkylsulfonyl)-methane
  申请人：——

  公开号：US20040116617A1

  公开（公告）日：2004-06-17

  The present invention provides a solid acid catalyst that is excellent from the point of toxicity, environment and others, wherein reaction can be progressed effectively with Bronsted acid or Lewis acid catalyst. For example, the benzoylation reaction of alcohol can also be progressed easily, and further, the catalyst can be recovered and recycled easily. The para position of arylbis(perfluoroalkylsulfonyl)methane represented by the general formula [1] (wherein R 1 shows a substituted or unsubstituted aryl group, Rf 1 and Rf 2 are independent to each other and show a perfluoroalkyl group), a pentafluorophenylbis(perfluoroalkylsulfonyl)methane, for example, is supported on a polystyrene resin, and a polystyrene-supported arylbis(perfluoroalkylsulfonyl)methane represented by the general formula [3] (wherein R 3 shows a substituted or unsubstituted arylene group, Rf 1 and Rf 2 are the same as described above) is obtained. 1 2

  本发明提供了一种固体酸催化剂，从毒性、环境等方面来看表现出色，其中可以有效地使用布朗斯特酸或路易斯酸催化剂进行反应。例如，醇的苯甲酰化反应也可以轻松进行，并且催化剂可以方便地回收和再利用。通式［1］中表示的芳基双（全氟烷基磺酰基）甲烷的对位，其中R1表示取代或未取代的芳基基团，Rf1和Rf2相互独立并显示全氟烷基，例如，被支持在聚苯乙烯树脂上的五氟苯基双（全氟烷基磺酰基）甲烷，得到通式［3］中表示的聚苯乙烯支持的芳基双（全氟烷基磺酰基）甲烷，其中R3表示取代或未取代的芳撑基团，Rf1和Rf2与上述相同。
• Arylbis(perfluoroalkylsulfonyl) methane and metallic salt thereof and methods for producing the same
  申请人：——

  公开号：US20040030192A1

  公开（公告）日：2004-02-12

  The present invention provides a method for producing various types of arylbis(perfluoroalkylsulfonyl)methane having a bulky aryl group and an electron-accepting aryl group in which synthesis was conventionally considered to be difficult, at high efficiency; a novel arylbis(perfluoroalkylsulfonyl)methane that can be widely applied to asymmertric catalyst, various types of functional materials and the like; and a metallic salt thereof. In addition, excellent catalysts are also provided. An aryl halomethane is reacted with a sodium trifluoromethane sulfinate, the arylmethyl triflone produced thereby is reacted with a t-BuLi and the like, the lithium salt of the arylmethyl triflone obtained is reacted with a trifluoromethane sulfonic acid anhydride, and an arylbis(trifluoromethylsulfony)methane such as pentafluorophenylbis(triflyl)methane, {4-(pentafluorophenyl)-2,3,5,6-tetrafluorophenyl}bis(triflyl)methane and the like are obtained at a high yield.

  本发明提供了一种高效率生产具有笨重芳基和电子受体芳基的各种类型的芳基双(全氟烷基磺酰)甲烷的方法，该合成在传统上被认为是困难的；一种可以广泛应用于不对称催化剂、各种类型的功能材料等的新型芳基双(全氟烷基磺酰)甲烷；以及其金属盐。此外，还提供了优秀的催化剂。将芳基卤代甲烷与三氟甲烷磺酸钠反应，所产生的芳基甲基三氟甲烷磺酸盐与t-BuLi等反应，得到芳基甲基三氟甲烷磺酸锂盐，再与三氟甲烷磺酸酐反应，得到芳基双(三氟甲烷基磺酰)甲烷，如五氟苯基双(三氟甲烷基磺酰)甲烷、4-(五氟苯基)-2,3,5,6-四氟苯基双(三氟甲烷基磺酰)甲烷等，收率高。
• Arylbis (perfluoroalkylsulfonyl)methane and metallic salt thereof, and methods for producing the same
  申请人：Ishihara Kazuaki

  公开号：US20050070741A1

  公开（公告）日：2005-03-31

  The present invention provides a method for producing various types of arylbis(perfluoroalkylsulfonyl)methane having a bulky aryl group and an electron-accepting aryl group in which synthesis was conventionally considered to be difficult, at high efficiency; a novel arylbis(perfluoroalkylsulfonyl)methane that can be widely applied to asymmertric catalyst, various types of functional materials and the like; and a metallic salt thereof. In addition, excellent catalysts are also provided. An aryl halomethane is reacted with a sodium trifluoromethane sulfinate, the arylmethyl triflone produced thereby is reacted with a t-BuLi and the like, the lithium salt of the arylmethyl triflone obtained is reacted with a trifluoromethane sulfonic acid anhydride, and an arylbis (trifluoromethylsulfony)methane such as pentafluorophenylbis(triflyl)methane, 4-(pentafluorophenyl)-2,3,5,6-tetrafluorophenyl}bis(triflyl)methane and the like are obtained at a high yield.

  本发明提供了一种高效生产具有笨重芳基和电子受体芳基的各种类型的芳基双(全氟烷基磺酰基)甲烷的方法，该合成通常被认为很难；一种新型的芳基双(全氟烷基磺酰基)甲烷，可广泛应用于不对称催化剂、各种类型的功能材料等；以及其金属盐。此外，还提供了优良的催化剂。将芳基卤代甲烷与三氟甲烷磺酰酸钠反应，得到芳基甲基三氟甲烷磺酰酸盐，再与t-BuLi等反应，得到芳基甲基三氟甲烷磺酸锂盐，最后与三氟甲烷磺酸酐反应，得到高产率的芳基双(三氟甲基磺酰基)甲烷，如五氟苯基双(三氟甲基磺酰基)甲烷、4-(五氟苯基)-2,3,5,6-四氟苯基}双(三氟甲基磺酰基)甲烷等。
• ARYLBIS (PERFLUOROALKYLSULFONYL) METHANE, METAL SALT OF THE SAME, AND PROCESSES FOR PRODUCING THESE
  申请人：JAPAN SCIENCE AND TECHNOLOGY CORPORATION

  公开号：EP1344772A1

  公开（公告）日：2003-09-17

  The present invention provides a method for producing various types of arylbis(perfluoroalkylsulfonyl)methane having a bulky aryl group and an electron-accepting aryl group in which synthesis was conventionally considered to be difficult, at high efficiency; a novel arylbis(perfluoroalkylsulfonyl)methane that can be widely applied to asymmertric catalyst, various types of functional materials and the like; and a metallic salt thereof. In addition, excellent catalysts are also provided. An aryl halomethane is reacted with a sodium trifluoromethane sulfinate, the arylmethyl triflone produced thereby is reacted with a t-BuLi and the like, the lithium salt of the arylmethyl triflone obtained is reacted with a trifluoromethane sulfonic acid anhydride, and an arylbis(trifluoromethylsulfony)methane such as pentafluorophenylbis(triflyl)methane, 4-(pentafluorophenyl)-2,3,5,6-tetrafluorophenyl}bis(triflyl)methane and the like are obtained at a high yield.

  本发明提供了一种高效生产各种类型芳基双(全氟烷基磺酰基)甲烷的方法，这些甲烷具有传统上被认为难以合成的大块芳基和电子接受芳基；提供了一种新型芳基双(全氟烷基磺酰基)甲烷，可广泛应用于异氰酸酯催化剂、各种功能材料等；还提供了其金属盐。此外，还提供了优良的催化剂。芳基卤代甲烷与三氟甲烷亚磺酸钠反应，由此生成的芳基甲基三氟丙烯与 t-BuLi 等反应，得到的芳基甲基三氟丙烯的锂盐与三氟甲烷磺酸酐反应、高产率地获得芳基双(三氟甲基磺酰基)甲烷，如五氟苯基双(三氟甲基)甲烷、4-(五氟苯基)-2,3,5,6-四氟苯基}双(三氟甲基)甲烷等。
• POLYMER-SUPPORTED ARYLBIS(PERFLUOROALKYLSULFONYL)-METHANE
  申请人：JAPAN SCIENCE AND TECHNOLOGY CORPORATION

  公开号：EP1375532A1

  公开（公告）日：2004-01-02

  The present invention provides a solid acid catalyst that is excellent from the point of toxicity, environment and others, wherein reaction can be progressed effectively with Bronsted acid or Lewis acid catalyst. For example, the benzoylation reaction of alcohol can also be progressed easily, and further, the catalyst can be recovered and recycled easily. The para position of arylbis(perfluoroalkylsulfonyl)methane represented by the general formula [1] (wherein R1 shows a substituted or unsubstituted aryl group, Rf1 and Rf2 are independent to each other and show a perfluoroalkyl group), a pentafluorophenylbis(perfluoroalkylsulfonyl)methane, for example, is supported on a polystyrene resin, and a polystyrene-supported arylbis(perfluoroalkylsulfonyl)methane represented by the general formula [3] (wherein R3 shows a substituted or unsubstituted arylene group, Rf1 and Rf2 are the same as described above) is obtained. (Chemical formula 1) (Chemical formula 2)

  本发明提供了一种在毒性、环境和其他方面都很好的固体酸催化剂，在使用勃朗斯特德酸或路易斯酸催化剂的情况下，反应可以有效地进行。例如，醇的苯甲酰化反应也可以很容易地进行，而且催化剂可以很容易地回收和循环使用。以通式 [1] 表示的芳基双(全氟烷基磺酰基)甲烷的对位为例（其中 R1 表示取代或未取代的芳基，Rf1 和 Rf2 相互独立并表示全氟烷基），将五氟苯基双(全氟烷基磺酰基)甲烷支撑在聚苯乙烯树脂上，并将聚苯乙烯支撑的 其中 R3 表示取代或未取代的芳基，Rf1 和 Rf2 与上述相同）。 (化学式 1） (化学式 2）