9,9,10,10,11,11,12,12,13,13,14,14,15,15,16,16,16-heptadecafluoro-7-hexadecyne | 84201-58-1

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氟化物
• 英文名称: 9,9,10,10,11,11,12,12,13,13,14,14,15,15,16,16,16-heptadecafluoro-7-hexadecyne
• 英文别名: 1-(F-octyl)-1-octyne；9,9,10,10,11,11,12,12,13,13,14,14,15,15,16,16,16-Heptadecafluorohexadec-7-yne
• CAS: 84201-58-1
• 化学式: C₁₆H₁₃F₁₇
• 分子量: 528.252
• InChiKey: UHLRDWLPIBLJGY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  17

反应信息

• 作为产物：
  描述：

  全氟辛基碘烷 、 1-辛炔 在 三氟乙酸 、 锌 、 potassium tert-butylate 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 2.0h， 生成 9,9,10,10,11,11,12,12,13,13,14,14,15,15,16,16,16-heptadecafluoro-7-hexadecyne
  参考文献：
  名称：

  Facile syntheses of various per- or polyfluoroalkylated internal acetylene derivatives

  摘要：

  Treatment of per- or polyfluoroalkylated vinyl iodides 5 with 2 equiv. of n-BuLi in THF produced the corresponding lithium acetylides in situ, which were transformed into zinc acetylides by the addition of ZnCl2.TMEDA complex into the reaction mixture. The in situ generated zinc acetylides were exposed to the cross-coupling conditions such as ArI/cat. Pd(PPh3)(4), reflux, 6-12 h, giving rise to the desired per- or polyfluoroalkylated acetylenes in high yields. In the case of trifluoromethylated acetylene, commercially available 2-bromo-3,3,3-trifluoropropene 6 could also be used instead of 5 as the starting material. In the acetylenes having a fluoroalkyl group and an aliphatic side chain, vinyl iodides 7, prepared by radical addition of perfluoroalkyl iodide to terminal acetylenes, were treated with t-BuOK at room temperature or at the reflux temperature of benzene, affording the desired compounds in good yields. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)01199-2

文献信息

• Perfluoroalkylations of Carbanions with (Perfluoroalkyl)phenyliodonium Triflates (FITS Reagents)
  作者：Teruo Umemoto、Yoshihiko Gotoh

  DOI：10.1246/bcsj.59.439

  日期：1986.2

  smoothly with enolate anions of active methylene compounds such as 2-methyl-1,3-cyclopentanedione, ethyl 2-methylacetoacetate, and ethyl 2-oxocyclopentanecarboxylate in a polar solvent to afford O- and C-perfluoroalkylation products in moderate yields, ratios O-/C-Rf products depending on the reaction temperature. Anions of diethyl 2-methylmalonate and 2-nitropropane afforded C-Rf-compounds only.

  FITS 试剂在-78 °C 的 THF 中与伯烷基卤化镁反应，以中等至良好的产率得到相应的全氟烷基 (Rf)-烷烃。但是烷基锂或铜的 Rf 产物产率很低。FITS 与仲或叔烷基卤化镁的反应导致产物收率低。炔基-锂或卤化镁以有利的产率产生Rf-炔烃。与芳基或乙烯基卤化镁的反应复杂且Rf衍生物的产率低。FITS 还与活性亚甲基化合物（如 2-甲基-1,3-环戊二酮、2-甲基乙酰乙酸乙酯和 2-氧代环戊烷羧酸乙酯）的烯醇阴离子在极性溶剂中顺利反应，以中等产率得到 O-和 C-全氟烷基化产物， O-/C-Rf 产物的比率取决于反应温度。
• Perfluoroalkylation of alkynes with RfI(Ph)OSO2CF3
  作者：Teruo Umemoto、Yuriko Kuriu、Osamu Miyano

  DOI：10.1016/s0040-4039(00)87675-3

  日期：1982.1
• Unexpected coupling reaction of (F-alkyl)iodides with 1-bromo-1-octyne: access to 1-(F-alkyl)-1-octynes
  作者：Véronique Sanchez、Jacques Greiner

  DOI：10.1016/0022-1139(93)02998-t

  日期：1994.7

  (F-Alkyl)iodides react with 1-bromo-1-octyne in the presence of a radical initiator [alpha,alpha'-azobis(isobutyronitrile)] to give mainly coupling products, 1-(F-alkyl)-1-octynes.
• UMEMOTO, TERUO;KURIU, YURIKO;MIYANO, OSAMU, TETRAHEDRON LETT., 1982, 23, N 35, 3579-3582
  作者：UMEMOTO, TERUO、KURIU, YURIKO、MIYANO, OSAMU

  DOI：——

  日期：——
• UMEMOTO, TERUO;GOTOH, YOSHIHIKO, BULL. CHEM. SOC. JAP., 1986, 59, N 2, 439-445
  作者：UMEMOTO, TERUO、GOTOH, YOSHIHIKO

  DOI：——

  日期：——