Dimethyl-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-Heptadecafluoro-undecyl)amine | 148171-75-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: Dimethyl-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-Heptadecafluoro-undecyl)amine
• 英文别名: dimethyl-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecyl)amine；N,N-dimethyl(3-perfluorooctylpropyl)amine；N,N-dimethyl 3-(F-octyl)-propylamine；Dimethyl-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoro-undecyl)-amine；4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoro-N,N-dimethylundecan-1-amine
• CAS: 148171-75-9
• 化学式: C₁₃H₁₂F₁₇N
• 分子量: 505.218
• InChiKey: ORMKUWWWCSWETH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  Dimethyl-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-Heptadecafluoro-undecyl)amine 在 双氧水 作用下， 以 溶剂黄146 为溶剂， 反应 16.0h， 以45%的产率得到N,N-dimethyl, N-<(3-F-octyl)propyl> amine oxide
  参考文献：
  名称：

  Synthesis and bioacceptability of fluorinated surfactants derived from F-alkylated tertiary amines

  摘要：

  Two methods for synthesizing tertiary F-alkylated amines are reported. The more general method allows the access in 56-87% yields to various NN-dialkyl F-alkyl amines. These amines are key intermediates leading in 52-96% yields to several families of surfactants, including zwitterionic and cationic derivatives and amine oxides, potentially useful in the formulation of fluorocarbon emulsions for diagnostic and therapeutic uses. The toxicity of the new surfactants and the influence of the polar head were assessed: the long chain compounds (8, 9 and 10) were found to be toxic for cell cultures and the zwitterionic compounds (7b and 8) have a LD50 < 250 mg.kg bw-1 in mice. The hemolysis test highlights the influence of the polar head: the zwitterionic compounds (7 and 8) were found to be non-hemolytic even at remarkably high concentrations (100 g l-1 for 8), whereas the cationic compounds 9 are highly hemolytic even at very low concentrations (0.05 g l-1).

  DOI：

  10.1016/0223-5234(92)90020-2
• 作为产物：
  描述：

  2-氨基甲苯-5-磺酸 在 lithium aluminium tetrahydride 、 氯化亚砜 作用下， 以 乙醚 为溶剂， 反应 50.0h， 生成 Dimethyl-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-Heptadecafluoro-undecyl)amine
  参考文献：
  名称：

  Synthesis and bioacceptability of fluorinated surfactants derived from F-alkylated tertiary amines

  摘要：

  Two methods for synthesizing tertiary F-alkylated amines are reported. The more general method allows the access in 56-87% yields to various NN-dialkyl F-alkyl amines. These amines are key intermediates leading in 52-96% yields to several families of surfactants, including zwitterionic and cationic derivatives and amine oxides, potentially useful in the formulation of fluorocarbon emulsions for diagnostic and therapeutic uses. The toxicity of the new surfactants and the influence of the polar head were assessed: the long chain compounds (8, 9 and 10) were found to be toxic for cell cultures and the zwitterionic compounds (7b and 8) have a LD50 < 250 mg.kg bw-1 in mice. The hemolysis test highlights the influence of the polar head: the zwitterionic compounds (7 and 8) were found to be non-hemolytic even at remarkably high concentrations (100 g l-1 for 8), whereas the cationic compounds 9 are highly hemolytic even at very low concentrations (0.05 g l-1).

  DOI：

  10.1016/0223-5234(92)90020-2

文献信息

• [EN] BIOCIDAL COMPOUND, ITS PRODUCTION PROCESS AND WOOD PRESERVATIVE COMPOSITION<br/>[FR] COMPOSÉ BIOCIDE, SON PROCÉDÉ DE PRODUCTION ET COMPOSITION DE PRÉSERVATION DU BOIS
  申请人：CONSEJO NAC INVEST CIENT TEC

  公开号：WO2015028942A1

  公开（公告）日：2015-03-05

  A biocidal compound characterized in that it comprises the following molecule (Figure 2): wherein: R1 is selected from the group comprised of methyl and propylene, and R2 is selected from the group comprised of C12H25, C15H25 and C11F17H6 A process for making it, and a wood preservative composition comprising it.

  一种生物杀灭化合物，其特征在于它包括以下分子（图2）：其中：R1选自甲基和丙烯基组，R2选自十二碳二十五、十五碳二十五和十一氟十七六氢基组。一种制备该化合物的方法，以及包含它的木材防腐剂组合物。
• Amphiphilic perfluoroalkylated sulfones and sulfonate betaines
  作者：Robert Kaplánek、Oldřich Paleta

  DOI：10.1016/j.jfluchem.2007.02.011

  日期：2007.7

  overall yields of two-step syntheses were above 90%. The compounds 7–9 were prepared by the reaction of oxiranes 1–3 with 2-sulfanylethan-l-ol and subsequent oxidation of intermediate sulfides. Similarly, the amphiphiles 13–15 were obtained by analogous reaction of oxiranes 1–3 with thiomorpholine and subsequent oxidation of the sulfur atom in the morpholine ring. In the syntheses of betaines 23–32, the

  两种类型的全氟烷基的含两亲砜的7 - 9和13 - 15，分别和磺酸盐甜菜碱23 - 32使用2制备- [（全氟烷基）甲基]环氧乙烷（1-3，R ˚F  = C 4 ˚F 9， C 6 F 13，C 8 F 17）或3-（全氟烷基）丙基碘（16和17，R F  = C 6 F 13，C 8 F 17）作为起始化合物。两步合成的总产率高于90％。化合物7 – 9是由[oxiranes] 1 – 3与2-sulfanylethan-1-ol反应并随后氧化中间体硫化物而制备的。类似地，两亲物13 - 15通过环氧乙烷的类似反应得到13与硫代吗啉和在吗啉环中的硫原子的后续氧化。在甜菜碱23 – 32的合成中，起始化合物1 – 3或16和17 首先使它们与二甲胺反应，然后使中间氟烷基（二甲基）胺与丙烷-1,3-或丁烷-1,4-内酯进行开环反应。
• Convenient syntheses and characterization of fluorophilic perfluorooctyl-propyl amines and ab initio calculations of proton affinities of related model compounds
  作者：Zoltán Szlávik、Gábor Tárkányi、Ágnes Gömöry、György Tarczay、József Rábai

  DOI：10.1016/s0022-1139(00)00398-5

  日期：2001.3

  step alkylation with Rf8(CH2)3I is described. The fluorophilicity values of 1–6 were determined by GC and range from 0.79±0.07 (1) to 5.3±0.2 (3). Systematic ab initio calculations of proton affinities of model compounds (7a–j) using Hartree–Fock and density functional theory imply that the inserted trimethylene spacer unit efficiently reduces the electron-withdrawing effect of the perfluorinated segment

  为全氟辛基-丙基胺的制备（A方便和有效的方法[R F8（CH 2）3 ] ñ NH 3- Ñ（1 - 3），Ñ = 1,2,3; R F8（CH 2）3 NHMe （4）； [R f8（CH 2）3 ] 2 NMe（5）； R f8（CH 2）3 NMe 2（6）； R f8 = F（CF 2）8）描述了通过与R f8（CH 2）3 I逐步烷基化的方法。的fluorophilicity值1 - 6通过GC测定以及从0.79±0.07（范围1）到5.3±0.2（3）。使用Hartree-Fock和密度泛函理论对模型化合物（7a – j）的质子亲和力进行系统的从头计算，表明所插入的三亚甲基间隔单元可有效降低全氟链段的电子吸收效应。所有结构均通过多核一维和二维NMR实验验证，其中涉及同核（）和杂核（，- ，– ）基于GMQFCOPS和反向和/或检测到的GHSQC，GHMQC序列与宽带绝热解耦的相关性。
• Nivet J.-B., Le Blanc M., Haddach M., Lanier M., Pastor R., Riess J. G., New J. Chem, 18 (1994) N 7, S 861-869
  作者：Nivet J.-B., Le Blanc M., Haddach M., Lanier M., Pastor R., Riess J. G.

  DOI：——

  日期：——
• Synthesis and bioacceptability of fluorinated surfactants derived from F-alkylated tertiary amines
  作者：JB Nivet、R Bernelin、M Le Blanc、JG Riess

  DOI：10.1016/0223-5234(92)90020-2

  日期：1992.12

  Two methods for synthesizing tertiary F-alkylated amines are reported. The more general method allows the access in 56-87% yields to various NN-dialkyl F-alkyl amines. These amines are key intermediates leading in 52-96% yields to several families of surfactants, including zwitterionic and cationic derivatives and amine oxides, potentially useful in the formulation of fluorocarbon emulsions for diagnostic and therapeutic uses. The toxicity of the new surfactants and the influence of the polar head were assessed: the long chain compounds (8, 9 and 10) were found to be toxic for cell cultures and the zwitterionic compounds (7b and 8) have a LD50 < 250 mg.kg bw-1 in mice. The hemolysis test highlights the influence of the polar head: the zwitterionic compounds (7 and 8) were found to be non-hemolytic even at remarkably high concentrations (100 g l-1 for 8), whereas the cationic compounds 9 are highly hemolytic even at very low concentrations (0.05 g l-1).