3,3,4,4,5,5,5-七氟戊炔 | 80337-25-3

• 分子结构分类: 有机化合物 - 乙炔化物
• 中文名称: 3,3,4,4,5,5,5-七氟戊炔
• 英文名称: n-heptafluoroproyplacetylene
• 英文别名: heptafluoropropylacetylene；3,3,4,4,5,5,5-Heptafluoropent-1-yne
• CAS: 80337-25-3
• 化学式: C₅HF₇
• mdl: MFCD00082621
• 分子量: 194.052
• InChiKey: GQXURUTWTUSYPE-UHFFFAOYSA-N

物化性质

• 沸点：
  18-20°C 710mm
• 密度：
  1.457±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  7

安全信息

• 安全说明：
  S16
• 危险类别码：
  R10
• 危险品运输编号：
  UN 1993

反应信息

• 作为反应物：
  描述：

  3,3,4,4,5,5,5-七氟戊炔 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 4.33h， 生成 4H,4H-5-dimethoxytetradecafluorooctane
  参考文献：
  名称：

  氟化α-二酮及其中间体的合成

  摘要：

  全氟烷基铜化合物与α-酮酰氯的反应用于氟化α-二酮的合成。由铜青铜和1-碘七氟丙烷制得的七氟丙基铜与苯甲酰基甲酰氯反应生成七氟-1-苯基-1,2-戊二酮，再与三甲基丙酮酰氯反应生成2,2-二甲基-5,5,6,6,7,7， 7-七氟-3,4-庚二酮，并与3,3,4,4,5,5,5-七氟-2-酮戊戊酰氯或草酰氯一起生成十四氟-4,5-辛二酮。描述了通过上述途径和其他方法合成氟化乙炔，氰醇，α-羟基酸，α-酮酸，它们的氯化物以及用于合成α-二酮的其他中间体。

  DOI：

  10.1016/s0022-1139(00)82657-3
• 作为产物：
  描述：

  3,3,4,4,5,5,5-heptafluoro-1-iodopentene 在 氢氧化钾 作用下， 以65.5%的产率得到3,3,4,4,5,5,5-七氟戊炔
  参考文献：
  名称：

  氟化α-二酮及其中间体的合成

  摘要：

  全氟烷基铜化合物与α-酮酰氯的反应用于氟化α-二酮的合成。由铜青铜和1-碘七氟丙烷制得的七氟丙基铜与苯甲酰基甲酰氯反应生成七氟-1-苯基-1,2-戊二酮，再与三甲基丙酮酰氯反应生成2,2-二甲基-5,5,6,6,7,7， 7-七氟-3,4-庚二酮，并与3,3,4,4,5,5,5-七氟-2-酮戊戊酰氯或草酰氯一起生成十四氟-4,5-辛二酮。描述了通过上述途径和其他方法合成氟化乙炔，氰醇，α-羟基酸，α-酮酸，它们的氯化物以及用于合成α-二酮的其他中间体。

  DOI：

  10.1016/s0022-1139(00)82657-3

文献信息

• Reactions of fluoroalk-1-en-1-yltrifluoroborate and perfluoroalk-1-yn-1-yltrifluoroborate salts and selected hydrocarbon analogues with hydrogen fluoride and with halogenating agents in aHF and in basic solvents
  作者：Vadim V. Bardin、Nicolay Yu. Adonin、Hermann-Josef Frohn

  DOI：10.1016/j.jfluchem.2011.09.011

  日期：2012.3

  products. In contrast, the salts K[RCFCFBF3] (R = CnF2n+1, trans-C4H9) and K[CF3CCBF3] underwent bromodeboration to RCFCFBr and CF3CCBr, respectively, when they were reacted with bromine in the polar solvents MeOH, MeCN, or sulfolane.

  K的电hydrodeboration [R'BF的相对速率3 ]与HF（27-100％）系列中的R'=减少Ç 4 ħ 9 Ç C> c ^ 4 ˚F 9 CF CFC C> CF 2 C（CF 3）> C 3 F 7 C C〜（CF 3）2 CFC C> CF 3 CC 。当R'= CF 3 C C时，通过添加获得新盐K [CF 3 CH 2 –CF 2 BF 3 ] CF 3 C以外的HF含量CH和K [BF 4 ]。少量水引起副产物K [CF 3 CH 2 –C（O）BF 3 ]的形成。全氟链烯基三氟硼酸盐与NCS或NBS在aHF（无水HF）中的亲电子卤代氟化作用导致K [R F CFHal–CF 2 BF 3 ]（来自K [R F CF CFBF 3 ]）和K [R F CFal 2 –CF 2 BF 3 ]（来自K [R F CHal CFBF 3 ]和K [R F C CBF 3
• Development of new approach for the synthesis of 6-perfluoroalkyl substituted allene benzazecines and study of the nature of properties due to the presence of perfluoroalkyl groups
  作者：Alexander A. Titov、Arina Y. Obydennik、Tatiana N. Borisova、Elena A. Sorokina、Leonid G. Voskressensky、Alexey V. Varlamov、Tuyet Anh Dang Thi、Nhat-Thuy-Giang Le、Tuan Anh Le

  DOI：10.1016/j.jfluchem.2023.110109

  日期：2023.4

  New approach for the introduction of a perfluoroalkynyl fragment into 1-R2–2-methyl-1,2,3,4-tetrahydroisoquinolines has been developed. Synthesized 1,1-disubstituted isoquinoline compounds under the action of methyl propiolate (24 °C) and acetylacetylene (-17 °C) in trifluoroethanol are converted into 6-perfluoroalkyl substituted allene benzazecines. The synthesized isoquinoline derivatives 2, and

  开发了将全氟炔基片段引入 1-R 2 –2-甲基-1,2,3,4-四氢异喹啉的新方法。合成的1,1-二取代异喹啉化合物在三氟乙醇中丙炔酸甲酯（24℃）和乙酰乙炔（-17℃）的作用下转化为6-全氟烷基取代的丙二烯苯并西辛。合成的异喹啉衍生物2和苯扎西因3 – 4针对四种癌细胞系进行了评估。结果表明化合物2h (R 2  = C 6 H 4 - p -OMe; R F  = CF(CF 3 ) 2) 对四种测试细胞系显示出良好的细胞毒性作用，IC 50值范围为 5 至 50 μM。
• Condensation of trichlorotrifluoropropylene and dichloroperfluoroisobutylene with fluorinated ethylenes in the presence of SbF5
  作者：V. A. Petrov、G. G. Belen'kii、L. S. German、A. P. Kurbakova、L. A. Leites

  DOI：10.1007/bf00954429

  日期：1982.1
• A general facile preparation of F-alkylacetylenes
  作者：Donald J. Burton、Terence D. Spawn

  DOI：10.1016/s0022-1139(00)85065-4

  日期：1988.1
• (Fluoroorgano)fluoroboranes and -borates. 14. Preparation of Potassium ((Perfluoroorgano)ethynyl)trifluoroborates K[R_FC⋮CBF₃]
  作者：Vadim V. Bardin、Nicolay Yu. Adonin、Hermann-Josef Frohn

  DOI：10.1021/om050590f

  日期：2005.10.1

  Despite the remarkable progress in organoboron chemistry, (alkynyl)fluoroborates remained unknown until 1999, when Darses et al. reported the preparation of the first two potassium (alkynyl)trifluoroborates, K[RC equivalent to CBF3] (R = Bu, Et3Si).(1) Later Molander et al. extended this series of salts with R = C8H17, C6H5, C6H5-CH(2)CH2, CClH2CH2CH2, CH2=C(CH3) Me3Si, and t-BuMe2SiOCH2CH2.(2) Both groups introduced (alkynyl)trifluoroborates successfully into Pd-catalyzed cross-coupling reactions and demonstrated impressively the application potential of alkynyltrifluoroborate salts.It is well-known that the replacement of all or the majority of hydrogen atoms by fluorine atoms in hydrocarbons or in their organoelement derivatives caused significant changes of their physical and chemical properties. 3 In this regard the chemistry of organoboron compounds is no exception. A recently published review presented a number of peculiarities which were derived from the combination of the specific properties of both roots, organofluorine and organoboron chemistry, and their co-action.(4)sWe have continued our systematic studies in the field of polyfluorinated organofluoroborates and -boranes investigated approaches to the synthesis of ((perfluoro-organo)ethynyl)trifluoroborate salts K[RFC equivalent to CBF3]. We have included perfluorinated alkyl, alkenyl, and aryl groups R-F attached to C-2 of the ethynyl unit.(5)