(Z)-2-fluoro-1-iodo-1-dodecene | 501018-38-8

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: (Z)-2-fluoro-1-iodo-1-dodecene
• 英文别名: (Z)-2-fluoro-1-iodododec-1-ene
• CAS: 501018-38-8
• 化学式: C₁₂H₂₂FI
• 分子量: 312.21
• InChiKey: GQRCRMFMBGCVGD-QXMHVHEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  14
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  反式-1-己烯-1-基硼酸 、 (Z)-2-fluoro-1-iodo-1-dodecene 在 氢氧化钾 、 四(三苯基膦)钯 作用下， 以 乙醇 、 苯 为溶剂， 反应 1.0h， 以83%的产率得到(5E,7Z)-8-fluoro-5,7-octadecadiene
  参考文献：
  名称：

  Stereoselective synthesis of fluoroalkenes via (Z)-2-fluoroalkenyliodonium salts

  摘要：

  Stereoselective synthesis of fluoroalkenes is described. (Z)-2-Fluoro-1-alkenyl(phenyl)iodonium tetrafluoroborates (1) were synthesized stereoselectively in good yields by Michael-type addition of HF to 1-alkynyl(phenyl)iodonium tetrafluoroborates (2) with a commercially available HF reagent, hydrofluoric acid or Et3N-3HF. Pd-catalyzed cross-coupling reactions using 1 gave (Z)-2-fluoro-l-alkene derivatives in moderate yields. The treatment of 1 with KI in the presence of a catalytic amount of CuI gave (Z)-2-fluoro-1-iodo-1-alkenes (3). Pd-catalyzed cross-coupling reactions of 3 gave better results than that of 1, and a variety of (Z)-2-fluoro-l-alkene derivatives were synthesized in good yields. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.05.085
• 作为产物：
  描述：

  (Z)-(2-fluoro-1-dodecenyl)(4-methylphenyl)iodonium tetrafluoroborate 在 copper(l) iodide 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 以89%的产率得到(Z)-2-fluoro-1-iodo-1-dodecene
  参考文献：
  名称：

  Stereoselective Synthesis of (Z)-2-Fluoro-1-alkenyl(phenyl)iodonium Tetrafluoroborates

  摘要：

  [GRAPHICS](Z)-2-Fluoro-1-alkenyl(phenyl)iodonium salts were stereoselectively prepared by the reaction of alkynyl(phenyl)Iodonium salts with aqueous HF in good yields. The method is applicable to the synthesis of fluoroalkenyliodonium salts having functional groups such as ketone, ester, and chloride. (Z)-2-Fluoro-1-alkene, (Z)-2-fluoro-2-alkenoate, and (Z)-beta-fluoroenyne could be stereoselectively prepared from the fluoroalkenyliodonium salt.

  DOI：

  10.1021/ol027512y

文献信息

• METHOD FOR PRODUCING FLUORINATED ORGANIC COMPOUND AND FLUORINATING REAGENT
  申请人：DAIKIN INDUSTRIES, LTD.

  公开号：US20150315136A1

  公开（公告）日：2015-11-05

  Object: An object of the present invention is to provide a method for producing, with a high yield, a fluorinated organic compound, the fluorinated organic compound having not been produced with a sufficient yield by a conventional method for producing a fluorinated organic compound using a fluorinating agent containing IF 5 -pyridine-HF alone. Another object of the present invention is to provide a fluorinating reagent. Means for achieving the object: A method for producing a fluorinated organic compound comprising step A of fluorinating an organic compound by bringing the organic compound into contact with (1) IF 5 -pyridine-HF and (2) at least one additive selected from the group consisting of amine hydrogen fluorides, X a F (wherein X a represents hydrogen, potassium, sodium, or lithium), oxidizers, and reducing agents.

  本发明的目的是提供一种高产的制备氟化有机化合物的方法，该氟化有机化合物通过使用仅含有IF5-吡啶-HF的氟化剂制备的传统方法无法获得足够的产量。本发明的另一个目的是提供一种氟化试剂。实现该目的的手段是提供一种制备氟化有机化合物的方法，包括步骤A：通过将有机化合物与(1)IF5-吡啶-HF和(2)至少选择自胺氢氟化物、XaF(其中X代表氢、钾、钠或锂)、氧化剂和还原剂组成的群体中的至少一种添加剂接触来进行氟化。
• METHOD FOR PRODUCING FLUORINATED IODINATED ORGANIC COMPOUND
  申请人：DAIKIN INDUSTRIES, LTD.

  公开号：US20220064098A1

  公开（公告）日：2022-03-03

  The present disclosure addresses the problem of providing a novel method for producing a fluorinated iodinated organic compound. The problem can be solved by a method for producing a fluorinated iodinated organic compound, comprising reacting a compound represented by formula (1): wherein R 1 and R 2 are each independently a hydrogen atom, a halogen atom, or an organic group, or R 1 and R 2 optionally form a ring together with the two adjacent carbon atoms; and n is 1 or 2, with a fluorine source, an iodine source, and an oxidizing agent or radical generator to add fluorine and iodine to the double bond or triple bond.

  本公开涉及提供一种生产氟碘有机化合物的新方法。该问题可以通过以下方法解决：提供一种生产氟碘有机化合物的方法，包括将由式（1）表示的化合物与氟源、碘源和氧化剂或自由基发生剂反应，其中R1和R2分别是氢原子、卤素原子或有机基团，或R1和R2可选择与两个相邻的碳原子一起形成环；n为1或2，以将氟和碘加到双键或三键上。
• COMPOSITION, FLUORINATING REAGENT, AND METHOD FOR PRODUCING FLUORINATED ORGANIC COMPOUND
  申请人：Daikin Industries, Ltd.

  公开号：EP3287431A1

  公开（公告）日：2018-02-28

  An object of the present invention is to provide a method for producing a fluorinated organic compound with a high yield without using carbon tetrachloride in view of the fact that the production of a fluorinated organic compound with a sufficient yield was impossible for a hitherto-known method that uses a fluorinating agent that contains IF5-pyridine-HF alone. Another object of the present invention is to provide a fluorinating reagent that is capable of achieving this object. The present invention provides a composition comprising (1) IF5 and (2) an aprotic solvent (with the proviso that carbon tetrachloride is excluded), wherein the aprotic solvent is contained in an amount within a range of 50 mass ppm to 20 mass%.

  本发明的一个目的是提供一种不使用四氯化碳就能高产率生产含氟有机化合物的方法，因为以前已知的仅使用含有 IF5-吡啶-HF的氟化剂的方法无法生产出足够产率的含氟有机化合物。本发明的另一个目的是提供一种能够实现这一目的的氟化试剂。本发明提供了一种组合物，该组合物包含 (1) IF5 和 (2) 一种壬烷溶剂（但不包括四氯化碳），其中壬烷溶剂的含量在 50 质量ppm 至 20 质量％的范围内。
• Composition, fluorinating reagent, and method for producing fluorinated organic compound
  申请人：DAIKIN INDUSTRIES, LTD.

  公开号：US11091432B2

  公开（公告）日：2021-08-17

  An object of the present invention is to provide a method for producing a fluorinated organic compound with a high yield without using carbon tetrachloride in view of the fact that the production of a fluorinated organic compound with a sufficient yield was impossible for a hitherto-known method that uses a fluorinating agent that contains IF5-pyridine-HF alone. Another object of the present invention is to provide a fluorinating reagent that is capable of achieving this object. The present invention provides a composition comprising (1) IF5 and (2) an aprotic solvent (with the proviso that carbon tetrachloride is excluded), wherein the aprotic solvent is contained in an amount within a range of 50 mass ppm to 20 mass %.

  本发明的一个目的是提供一种不使用四氯化碳就能高产率生产含氟有机化合物的方法，因为以前已知的仅使用含有 IF5-吡啶-HF的氟化剂的方法无法生产出足够产率的含氟有机化合物。本发明的另一个目的是提供一种能够实现这一目的的氟化试剂。本发明提供了一种组合物，该组合物包含 (1) IF5 和 (2) 一种烷基溶剂（但不包括四氯化碳），其中烷基溶剂的含量在 50 质量 ppm 至 20 质量 % 的范围内。
• Stereoselective Synthesis of (<i>Z</i>)-2-Fluoro-1-alkenyl(phenyl)iodonium Tetrafluoroborates
  作者：Masanori Yoshida、Shoji Hara

  DOI：10.1021/ol027512y

  日期：2003.2.1

  [GRAPHICS](Z)-2-Fluoro-1-alkenyl(phenyl)iodonium salts were stereoselectively prepared by the reaction of alkynyl(phenyl)Iodonium salts with aqueous HF in good yields. The method is applicable to the synthesis of fluoroalkenyliodonium salts having functional groups such as ketone, ester, and chloride. (Z)-2-Fluoro-1-alkene, (Z)-2-fluoro-2-alkenoate, and (Z)-beta-fluoroenyne could be stereoselectively prepared from the fluoroalkenyliodonium salt.