(E)-2-fluoro-1-iodo-1-dodecene | 207683-44-1

• 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: (E)-2-fluoro-1-iodo-1-dodecene
• 英文别名: (E)-2-fluoro-1-iodododec-1-ene
• CAS: 207683-44-1
• 化学式: C₁₂H₂₂FI
• 分子量: 312.21
• InChiKey: GQRCRMFMBGCVGD-VAWYXSNFSA-N

物化性质

• 沸点：
  275.9±10.0 °C(Predicted)
• 密度：
  1.277±0.06 g/cm3(Predicted)

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：

  哌喃 、 (E)-2-fluoro-1-iodo-1-dodecene 在 palladium diacetate copper(l) iodide 、 三苯基膦 作用下， 以 二乙胺 为溶剂， 反应 12.0h， 以90%的产率得到(E)-5-fluoro-1-(2-tetrahydropyranyloxy)-4-pentadecen-2-yne
  参考文献：
  名称：

  Stereoselective synthesis of (E)-1-fluoro-1,3-enynes

  摘要：

  1-Fluoro-1,3-enynes were stereoselectively prepared by the cross-coupling reaction of 1-alkynes with beta -fluoroalkenyliodides obtained from (beta -fluoroalkenyl)iodonium salts. As the reaction proceeds under mild conditions, polyfunctionalized 1-fluoro-1,3-enynes could be prepared, and the synthesis of a fluorinated analog of a natural compound was achieved using this method. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00683-4
• 作为产物：
  描述：

  1-十二炔 在 iodine pentafluoride-pyridine-hydrogen fluoride 、 对苯二酚 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以65%的产率得到(E)-2-fluoro-1-iodo-1-dodecene
  参考文献：
  名称：

  使用IF 5-吡啶-HF通过炔烃的碘代氟化立体选择性合成碘代氟烯烃

  摘要：

  使用IF 5-吡啶-HF和对苯二酚进行炔烃的碘氟化。内部炔烃和末端炔烃的碘氟化立体选择性进行，得到相应的碘氟烯烃。不对称取代的内部炔烃和电子不足的炔烃还立体选择性地提供了相应的碘氟烯烃。由此获得的碘代氟代烯烃被用于二和三取代的氟代烯烃的立体选择性合成中。

  DOI：

  10.1016/j.tetlet.2016.02.063

文献信息

• Iodofluorination of Alkenes and Alkyne using Electrochemically Generated Iodonium Cation
  作者：Shingo Kobayashi、Masanori Sawaguchi、Shinichi Ayuba、Tsuyoshi Fukuhara、Shoji Hara

  DOI：10.1055/s-2001-18775

  日期：——

  Iodofluorination reaction of alkenes and alkynes using the iodonium ion electrochemically generated in situ from the iodide anion was carried out. The reaction proceeds at room temperature to provide iodofluorination products regioselectively.

  使用以碘离子现场电化学生成的碘鎓离子，对烯烃和炔烃进行碘氟化反应。该反应在室温下进行，可选择性地得到区域选择性的碘氟化产物。
• Stereo- and regio-selective addition of iodotoluene difluoride to alk-1-ynes. Selective synthesis of 2-fluoro-1-iodoalk-1-enes
  作者：Shoji Hara、Masaki Yoshida、Tsuyoshi Fukuhara、Norihiko Yoneda

  DOI：10.1039/a801273c

  日期：——

  p-Iodotoluene difluoride reacted with 1-alkynes to give trans adducts which could be converted to 2-fluoro-1-iodoalk-1-enes without isolation.

  对-碘甲苯二氟化物与1-炔反应，生成顺式加合物，不经分离即可转化为2-氟-1-碘代烯烃。
• Regio- and stereoselective synthesis of fluoroalkenes and fluoroalkadienes
  作者：Masanori Yoshida、Daisuke Ota、Tsuyoshi Fukuhara、Norihiko Yoneda、Shoji Hara

  DOI：10.1039/b108796g

  日期：2002.1.23

  (E)-Fluoroalkenes and (E,E)-fluoroalkadienes are synthesized stereoselectively from (E)-2-fluoro-1-iodoalk-1-enes by Pd-catalyzed cross-coupling reaction with organoboranes.

  (E)-氟代烯烃和(E,E)-氟代二烯烃可以通过钯催化的交叉偶联反应，从(E)-2-氟-1-碘代烯烃与有机硼试剂立体选择性地合成。
• 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。
• 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。