methyl 10-fluoro-11-iodoundecanoate | 134296-75-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 10-fluoro-11-iodoundecanoate
• CAS: 134296-75-6
• 化学式: C₁₂H₂₂FIO₂
• 分子量: 344.208
• InChiKey: ADTXNVJPGAFCOX-UHFFFAOYSA-N

物化性质

• 沸点：
  331.2±12.0 °C(Predicted)
• 密度：
  1.351±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  16
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  10-烯酸甲酯 在 triethylamine pentahydrogen fluoride salt 、 三乙基铵碘化物 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到methyl 10-fluoro-11-iodoundecanoate
  参考文献：
  名称：

  Iodofluorination of Alkenes and Alkyne using Electrochemically Generated Iodonium Cation

  摘要：

  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。

  DOI：

  10.1055/s-2001-18775

文献信息

• Iodine-Mediated Fluorination of Alkenes with an HF Reagent: Regioselective Synthesis of 2-Fluoroalkyl Iodides
  作者：Tsugio Kitamura、Ryuichi Komoto、Juzo Oyamada、Masahiro Higashi、Yosuke Kishikawa

  DOI：10.1021/acs.joc.1c02422

  日期：2021.12.17

  Fluorination reaction of alkenes with iodine and HF·pyridine complex (pyr·9HF) was performed under mild conditions in the presence of K2S2O8 or Na2S2O8 as an oxidant. Aliphatic and aromatic alkenes underwent iodofluorination to give the iodofluorinated products with high regioselectivity. The substitution reactions of the iodofluorinated product by nitrogen, sulfur, and oxygen nucleophiles indicated

  在K 2 S 2 O 8或Na 2 S 2 O 8氧化剂存在下，烯烃与碘和HF·吡啶络合物(pyr·9HF)的氟化反应在温和条件下进行。脂肪族和芳香族烯烃经过碘氟化反应得到具有高区域选择性的碘氟化产物。氮、硫和氧亲核试剂对碘氟化产物的取代反应表明其进一步用作合成 2-氟烷基取代化合物的构建单元。
• Selective Halofluorination of Alkenes with Tetrabutylphosphonium Dihydrogentrifluoride in Combination with<i>N</i>-Halosuccinimide or 1,3-Dibromo-5,5-dimethylhydantoin
  作者：Yukitaka Uchibori、Masayuki Umeno、Hideharu Seto、Hirosuke Yoshioka

  DOI：10.1246/cl.1993.673

  日期：1993.4

  Alkenes and their functionalized derivatives were readily converted to the corresponding halofluorides with tetrabutylphosphonium dihydrogentrifluoride as combined with N-halosuccinimides or 1,3-dibromo-5,5-dimethylhydantoin in highly regio-, stereo-, and chemoselective manners. In particular, alkenes having a oxirane or primary hydroxyl group also underwent halofluorination selectively in good yields

  烯烃及其官能化衍生物很容易通过四丁基二氢三氟化鏻与 N-卤代琥珀酰亚胺或 1,3-二溴-5,5-二甲基乙内酰脲以高度区域选择性、立体选择性和化学选择性的方式转化为相应的卤代氟化物。特别是，具有环氧乙烷或伯羟基的烯烃也以良好的产率选择性地进行卤氟化。
• Potassium Fluoride-Poly(Hydrogen Fluoride) Salts as Fluorinating Agents for Halofluorination of Alkenes
  作者：Masanori Tamura、Motonari Shibakami、Akira Sekiya

  DOI：10.1055/s-1995-3946

  日期：1995.5

  It was found that potassium fluoride-poly(hydrogen fluoride) salts are useful fluorine sources for halofluorination of alkenes. The reaction proceeded with these salts and N-halosuccinimides or 1,3-dibromo-5,5-dimethylhydantoin in a regio- and stereoselective manner.

  研究发现，氟化钾-聚氢氟化物盐是一种有用的氟源，用于烯烃的卤氟化反应。该反应以这些盐与N-卤代琥珀酰亚胺或1,3-二溴-5,5-二甲基海因在区域选择性和立体选择性条件下进行。
• Halofluorination of Alkenes Using Dilute Hydrofluoric Acid
  作者：Manabu Kuroboshi、Tamejiro Hiyama

  DOI：10.1246/bcsj.68.1799

  日期：1995.7

  Iodofluorination of alkenes was achieved with N-iodosuccinimide, potassium hydrogendifluoride, and 1 M hydrofluoric acid using tetrabutylammonium fluoride as a phase-transfer catalyst. The active fluorinating reagent was shown to be tetrabutylammonium dihydrogentrifluoride by preparing the salt in a different way and by effecting the same transformation under anhydrous conditions. Bromofluorination

  使用四丁基氟化铵作为相转移催化剂，用 N-碘代琥珀酰亚胺、二氟化氢钾和 1 M 氢氟酸实现烯烃的碘氟化。通过以不同的方式制备盐并在无水条件下进行相同的转化，活性氟化试剂显示为四丁基二氟化氢铵。烯烃的溴氟化也使用 1,3-二溴-5,5-二甲基乙内酰脲进行。用 DBU 处理 I-F 加合物可立体定向地提供氟烯烃。
• 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。