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Fatty trifluoroethyl ester compound and its preparation method

A technology for trifluoroethyl ester and compound is applied in the field of aliphatic trifluoroethyl ester compound and its preparation, which can solve the problems of poor atom utilization, low reaction efficiency, harsh reaction conditions and the like, achieves less side reactions and is beneficial to environmental protection , the effect of simple operation

Active Publication Date: 2022-02-01
JIANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] For reasons such as harsh reaction conditions of fatty trifluoroethyl esters, inconvenient operation, low reaction efficiency, and poor atom utilization, the purpose of the present invention is to prepare fatty trifluoroethyl esters in a one-step, one-pot method without catalysts.

Method used

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  • Fatty trifluoroethyl ester compound and its preparation method
  • Fatty trifluoroethyl ester compound and its preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1～16

[0027] The following implementations 1-16 are prepared according to the following synthetic route, and compounds 1-16 can be prepared:

[0028]

[0029] The specific operation is: dissolve the fatty acid (0.5mmol, 1equiv) substrate in 1,1,1,3,3,3-hexafluoro-2-propanol, and add tert-butyl nitrite ( 150μL, 1.25mmol, 2.5equiv) and 2,2,2-trifluoroethylamine (100μL, 1.25mmol, 2.5equiv), stirred for 5min and raised to room temperature to continue the reaction for 0.5~10h, and the solution in the reaction system was decompressed After spinning to dryness, the residue was purified by column chromatography to obtain fatty trifluoroethyl ester compounds.

Embodiment 1

[0031] Substrate: nonanoic acid

[0032] product:

[0033] Compound 1: colorless oil (107mg, 93% yield); IR(KBr)ν max / cm -1 :2959,2930,2859,1762, 1457,1412,1283,1170,1111,1067,979,842,807; 1 H NMR (400MHz, CDCl 3 )δ4.39(q, J=8.5 Hz, 2H, C H 2 CF 3 ), 2.34(t, J=7.5Hz, 2H, COC H 2 ),1.72–1.48(m,2H,COCH 2 C H 2 ), 1.22 (dd, J=12.8, 6.6Hz, 10H, C H 2 ),0.81(t,J=6.8Hz,3H,CH 2 C H 3 );13 C NMR (100MHz, CDCl 3 )δ 171.2(CO), 122.0(q, J=277.1Hz, C f 3 ),59.1(q,J=36.5Hz, C CF 3 ), 32.6 (CO C h 2 ), 30.8 (COCH 2 C h 2 ), 28.13, 28.08, 28.0, 23.7, 21.6, 13.0 (CH 2 C h 3 ); 19 F NMR (376MHz, CDCl 3 )δ -73.97(t, J=8.3Hz, C F 3 ); 19 F{ 1 H}NMR (376MHz, CDCl 3 )δ-73.97(s,C F 3 ); HRMS(ESI): m / zcalcd for C 11 h 29 f 3 o 2 Na + [M+Na] + 263.1229, found 263.1242.

Embodiment 2

[0035] Substrate: Heptanoic acid

[0036] product:

[0037] Compound 2: colorless oil (89mg, 84% yield); IR(KBr)ν max / cm -1 :2961,2931,2858,1756,1419, 1285,1172,1107,909,807,735; 1 H NMR (400MHz, CDCl 3 )δ4.47(q, J=8.5Hz, 2H, C H 2 CF 3 ), 2.42(t,J=7.5Hz,2H,COC H 2 ), 1.66 (p, J=7.5Hz, 2H, C H 2 CH 3 ),1.48–1.22(m,6H),0.88(t,J=6.9Hz,3H,C H 3 ); 13 C NMR (100MHz, CDCl 3 )δ172.2(CO), 123.0(q, J=277.1Hz, C h 2 CF 3 ), 60.1(q, J=36.4Hz, C f 3 ), 33.7 (CO C h 2 ),31.4( C h 2 ),28.7( C h 2 ),24.7( C h 2 ),22.5( C h 2 ),14.0 ( C h 3 ); 19 F NMR (376MHz, CDCl 3 )δ-73.85(t, J=8.5Hz, C F 3 ); 19 F{ 1 H}NMR (376MHz, CDCl 3 ) δ-73.85(s,C F 3 ); HRMS(ESI):m / z calcd for C 9 h 15 f 3 o 2 Na + [M+Na] + 235.0916,found235.0916.

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PUM

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Abstract

The invention relates to fatty trifluoroethyl ester compounds and a preparation method thereof. Wherein, the definition of fatty acid trifluoroethyl ester compound is the same as that in the claims. The preparation method includes the following steps: under low temperature conditions, add 2,2,2-trifluoroethylamine and tert-butyl nitrite into an organic solution in which fatty acids are dissolved, stir evenly, and continue to react at room temperature to obtain fatty acid three Fluoroethyl ester products. Wherein, the molar ratio of fatty acid to 2,2,2-trifluoroethylamine and tert-butyl nitrite is 1:(1-2.5):(1-2.5). The method of the present invention can obtain the target product without adding catalysts and other additives, has simple operation, mild reaction conditions, low cost, high yield, and is environmentally friendly, and can obtain trifluoroethyl esters of fats and drug molecule carboxylic acids Compounds are widely used.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to fatty trifluoroethyl ester compounds and a preparation method thereof. The present invention also relates to the use of the fatty trifluoroethyl ester compound in pharmaceutical, food, material and other industries. Background technique [0002] With the development of organic fluorine chemistry, fatty acid trifluoroethyl esters (RCO 2 CH 2 CF 3 ) compounds have attracted much attention. Due to its characteristics such as biodegradability, weak toxicity or even non-toxicity, some non-irritating and antibacterial and anti-oxidant properties, it is often used in pharmaceutical, food, beauty, processing and other industries. The currently known fatty acid trifluoroethyl esters used in the fields of medicine and materials are mainly unsaturated fatty acid trifluoroethyl esters, which are mainly used to synthesize ion exchange membranes, drug delivery media, ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07B41/12C07C67/00C07C69/63C07C69/732C07C69/712C07C69/757C07C269/06C07C271/22C07D209/28C07D307/93C07H1/00C07H15/04C07H17/07C07J9/00C07K5/062C07K5/065C07K5/078C07K1/113
CPCC07B41/12C07C67/00C07C269/06C07D209/28C07D307/93C07H1/00C07H15/04C07H17/07C07J9/005C07K1/113C07K5/06043C07K5/06078C07K5/06165C07C2601/16C07C2603/18C07C69/63C07C69/732C07C69/712C07C69/757C07C271/22
Inventor 胡祥国高玉彭山青
Owner JIANGXI NORMAL UNIV
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