1-fluoro-4-hydroxy-1,4-diazoniabicyclo[2,2,2]octane-1,4-bis(tetrafluoroborate)

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 1-fluoro-4-hydroxy-1,4-diazoniabicyclo[2,2,2]octane-1,4-bis(tetrafluoroborate)
• 英文别名: 1-fluoro-4-hydroxy-1,4-diazabicyclo[2.2.2]octane-1,4-diium tetrafluoroborate；1-fluoro-4-hydroxy-1,4-diazoniabicyclo-[2,2,2]-octane bis(tetrafluoroborate)；1-fluoro-4-hydroxy-1,4-diazoniabicyclo[2,2,2]octane bis(tetrafluoroborate)；1-fluoro-4-hydroxy-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)；1-hydroxy-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)；1-fluoro-4-hydroxy-1,4-diazoniabicyclo[2,2,2]octanebis(tetrafluoroborate)；1-Fluoro-4-hydroxy-1,4-diazoniabicyclo[2.2.2]octane;tetrafluoroborate；1-fluoro-4-hydroxy-1,4-diazoniabicyclo[2.2.2]octane;tetrafluoroborate
• 化学式: 2BF₄*C₆H₁₃FN₂O
• 分子量: 321.79
• InChiKey: GYRXGAGPYVMRFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.22
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-fluoro-4-hydroxy-1,4-diazoniabicyclo[2,2,2]octane-1,4-bis(tetrafluoroborate) 在 吡啶 作用下， 生成
  参考文献：
  名称：

  摘要：

  DOI：

  10.1023/a:1012436925944
• 作为产物：
  描述：

  1,4-diazabicyclo[2.2.2]octane N-oxide 在 tetrafluoroboric acid 、 三氟化硼 、 fluorine 作用下， 以 乙腈 为溶剂， 以75%的产率得到1-fluoro-4-hydroxy-1,4-diazoniabicyclo[2,2,2]octane-1,4-bis(tetrafluoroborate)
  参考文献：
  名称：

  1-氟-4-羟基-1,4-二氮杂双环[2.2.2]辛烷双（四氟硼酸酯）：亲电氟化剂

  摘要：

  1-氟-4-羟基-1,4-二氮杂双环[2.2.2]辛烷双（四氟硼酸酯）NFTh是一种亲电子氟化剂，可用于氟化芳族环，烯烃，乙酸二烯醇酯和烯醇醚。当NFTh在ZnCl 2存在下与活性亚甲基化合物反应时，可以分离出相应的单或二氟衍生物。

  DOI：

  10.1016/s0040-4039(99)00303-2
• 作为试剂：
  描述：

  4-硝基苯乙烯 、 乙腈 在 1-fluoro-4-hydroxy-1,4-diazoniabicyclo[2,2,2]octane-1,4-bis(tetrafluoroborate) 作用下， 以70%的产率得到
  参考文献：
  名称：

  Ritter-type fluorofunctionalisation as a new, effective method for conversion of alkenes to vicinal fluoroamides

  摘要：

  一系列烯烃通过与1-氟-4-羟基-1,4-二氮鎓双环[2.2.2]辛烷二(四氟硼酸盐)(AccufluorTM NFTh)在乙腈溶液中反应，高效转化为高产率的邻位氟乙酰胺类化合物。

  DOI：

  10.1039/cc9960002247

文献信息

• Benzimidazole derivatives for the treatment of viral infections
  申请人：The Regents of the University of Michigan

  公开号：US06413938B1

  公开（公告）日：2002-07-02

  According to a first aspect of the invention there is provided compounds of formula (I): wherein: R1 is hydroxy; O-acetyl; or a halo atom; R2 is hydroxy; O-acetyl; or a halo atom; R3 is hydrogen; a halo atom; azido; C2-6alkenyl; C2-6alkynyl; C6-14aryl C2-6alkenyl; C6-14arylC2-6alkynyl —NR8R9 (where R8 and R9 may be the same or different and are hydrogen, C1-8alkyl, cyanoC1-8alkyl, hydroxyC1-8alkyl, haloC1-8alkyl, C3-7cycloalkyl, C1-8alkylC3-7cycloalkyl, C2-6alkenyl, C3-7cycloalkylC1-8alkyl, C2-6alkynyl, C6-14aryl, C6-14arylC1-8alkyl, heterocycleC1-8alkyl, C1-8alkylcarbonyl, C6-14arylsulfonyl, C1-8alkysulfonyl, or R8R9 together with the N atom to which they are attached form a 3,4,5 or 6 membered heterocyclic ring); —OR10 (where R10 is hydrogen, C1-8alkyl, C6-14aryl, or C6-14arylC1-8alkyl, C2-6alkenyl, C2-6alkynyl, C6-14aryl C2-6alkenyl or C6-14arylC2-6alkynyl); or —SR11 (where R11 is hydrogen, C1-8alkyl, C6-14aryl, or C6-14arylC1-8alkyl).

  根据本发明的第一个方面，提供了以下式（I）的化合物：其中：R1是羟基；O-乙酰基；或卤原子；R2是羟基；O-乙酰基；或卤原子；R3是氢原子；卤原子；叠氮基；C2-6烯基；C2-6炔基；C6-14芳基C2-6烯基；C6-14芳基C2-6炔基-NR8R9（其中R8和R9可能相同也可能不同，为氢原子，C1-8烷基，氰基C1-8烷基，羟基C1-8烷基，卤基C1-8烷基，C3-7环烷基，C1-8烷基C3-7环烷基，C2-6烯基，C3-7环烷基C1-8烷基，C2-6炔基，C6-14芳基，C6-14芳基C1-8烷基，杂环C1-8烷基，C1-8烷基羰基，C6-14芳基磺酰基，C1-8烷基磺酰基，或R8R9与它们连接的N原子一起形成3,4,5或6个成员的杂环环）；-OR10（其中R10是氢原子，C1-8烷基，C6-14芳基，或C6-14芳基C1-8烷基，C2-6烯基，C2-6炔基，C6-14芳基C2-6烯基或C6-14芳基C2-6炔基）；或-SR11（其中R11是氢原子，C1-8烷基，C6-14芳基，或C6-14芳基C1-8烷基）。
• 1-substituted-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane salts and their
  申请人：AlliedSignal Inc.

  公开号：US05459267A1

  公开（公告）日：1995-10-17

  SUBSTITUTED-4-FLUORO-1,4-DIAZONIABICYCLO[2.2.2]OCTANE SALTS AND THEIR APPLICATION AS FLUORINATING AGENTS The present invention relates to the preparation and uses of 1-substituted-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane salts, specifically 1-hydroxyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane salts as reagents for the introduction of fluorine in organic compounds.

  本发明涉及1-取代-4-氟-1,4-二氮杂双环[2.2.2]辛烷盐的制备和用途，特别是1-羟基-4-氟-1,4-二氮杂双环[2.2.2]辛烷盐作为有机化合物中氟化试剂的引入剂。
• Process for the manufacture of
  申请人：AlliedSignal Inc.

  公开号：US05631372A1

  公开（公告）日：1997-05-20

  A process for producing 1-substituted-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane salts having the formula ##STR1## wherein the Z substituent is OH, OR, OC(O)R, SO.sub.3, SO.sub.2 R, NO.sub.2, NO, or PO(OR).sub.2, wherein R is an aryl or C.sub.1 -C.sub.8 alkyl group; n is 0, 1 or 2; each of R.sub.1, R.sub.2, R.sub.3, P.sub.4 and R.sub.5 independently represent hydrogen, C.sub.1 to C.sub.8 alkyl, or aryl 1-substituted-1,4-diazoniabicyclo[2.2.2]octane or 1,4-diazoniabicyclo[2.2.2]octane mono-N-oxide is reacted to attach the Z group and then the result is reacted with molecular fluorine in the presence of a solvent that substantially does not react with fluorine and a fluoride scavenger that results in an X counter ion. These compounds are useful as fluorinating agents for the introduction of fluorine into organic compounds.

  一种制备1-取代-4-氟-1,4-二氮杂双环[2.2.2]辛烷盐的方法，其化学式为##STR1##其中Z取代基为OH，OR，OC（O）R，SO.sub.3，SO.sub.2R，NO.sub.2，NO或PO（OR）.sub.2，其中R为芳基或C.sub.1-C.sub.8烷基；n为0、1或2；R.sub.1、R.sub.2、R.sub.3、P.sub.4和R.sub.5中的每一个独立地表示氢、C.sub.1到C.sub.8烷基或芳基1-取代-1,4-二氮杂双环[2.2.2]辛烷或1,4-二氮杂双环[2.2.2]辛烷单N-氧化物，以连接Z基，然后在不与氟反应的溶剂和氟离子清除剂的存在下，与分子氟反应，产生X离子。这些化合物可用作引入有机化合物中的氟化剂。
• 1-fluoro-4-hydroxy-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate): An electrophilic fluorinating agent
  作者：Andrew J. Poss、George A. Shia

  DOI：10.1016/s0040-4039(99)00303-2

  日期：1999.4

  1-Fluoro-4-hydroxy-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate), NFTh, is a electrophilic fluorinating that can be used to fluorinate aromatic rings, olefins, dienol acetates and enol ethers. When NFTh is reacted with an active methylene compound in the presence of ZnCl2, the corresponding monoor di-fluoro derivative can be isolated.

  1-氟-4-羟基-1,4-二氮杂双环[2.2.2]辛烷双（四氟硼酸酯）NFTh是一种亲电子氟化剂，可用于氟化芳族环，烯烃，乙酸二烯醇酯和烯醇醚。当NFTh在ZnCl 2存在下与活性亚甲基化合物反应时，可以分离出相应的单或二氟衍生物。
• ——
  作者：A. A. Fainzil'berg、V. I. Faustov

  DOI：10.1023/a:1012436925944

  日期：——