CN109734643A - The method that iron catalytic amino alcohol synthesizes pyrrolines with enol - Google Patents
The method that iron catalytic amino alcohol synthesizes pyrrolines with enol Download PDFInfo
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Abstract
A kind of method that the invention discloses iron catalytic amino alcohol to synthesize pyrrolines with enol, under atmosphere of inert gases, using amino alcohol and enol as raw material, potassium tert-butoxide is alkali, a series of pyrrolines are synthesized by the pure and mild enol dehydrogenation coupling of cheap transition metal iron catalytic amino and the fracture of carbon-carbon bond, system is simple, easy to operate, reaction condition is mild, and reaction substrate has good applicability.
Description
Technical field
The invention belongs to synthesize the technical field of pyrrolin and its derivative, and in particular to amino alcohol and enol in transition
Dehydrogenation coupling and the fracture of carbon-carbon bond synthesize the side of a series of pyrrolin and its derivative under the catalysts conditions of metallic iron
Method.
Background technique
Pyrrolin and its derivative have proved to be a kind of valuable intermediate and multi-functional N- heterocyclic compound.Due to
The bioactivity such as its potential antibacterial, anti-inflammatory, antitumor, weeding have very high using valence in medicine and field of pesticide production
Value.
The synthetic method of pyrrolin includes N- vinyl lactam, lactim ether, the halogenated nitrile of 4- and N- (trimethyl silyl
Base) lactams reacts with organometallic reagent (including lithium alkylide and magnesium halide etc.).Further, it is also possible in organic azide
Tertiary phosphine is added, the oxidation reaction of palladium chtalyst unsaturated amine synthesizes pyrrolin.2001, Pedro J.Campos seminar reported
Photocatalysis cyclopropyl imines resets synthesis pyrrolin.2004, Dalibor Sames seminar by catalysis pyrrolidines with it is halogenated
The dehydrogenation of aromatic hydrocarbons and arylation reaction synthesize pyrrolin.2009, Barbara A.Messerle seminar was urged using ruthenium and osmium
The intramolecular hydroamination for changing ynamine synthesizes pyrrolin.2016, Chang Junbiao seminar reported through cyclobutane formamide
The method of Hoffmann rearrangement ring-enlarging reaction synthesis pyrroline derivative.But it is reacted by amino alcohol and allyl alcohol, transition metal
Iron catalytic dehydrogenation coupling and carbon-carbon bond fracture are not reported also come the method for synthesizing pyrrolin.
Summary of the invention
The purpose of the present invention is to provide it is a kind of it is environmentally protective, pollution-free, reaction condition is mild, urged by transition metal iron
The method for changing amino alcohol and enol dehydrogenation coupling and carbon-carbon bond fracture synthesis pyrrolines.
For above-mentioned purpose, the technical scheme adopted by the invention is that: by enol shown in amino alcohol shown in Formulas I and Formula II,
Triethyl group Boratex, iron catalyst, potassium tert-butoxide are added in organic solvent, under inert gas protection, 120~135 DEG C of reactions,
Product is isolated and purified after fully reacting, obtains pyrrolines shown in formula III.
Ar represents phenyl, C in formula1~C4Alkyl-substituted phenyl, C1~C4Alkoxy substituted phenyl, halogenophenyl, benzo
[d] [1,3] dioxa cyclopentenyl, naphthalene, any one in phenanthryl, R1、R2、R3It is independent to represent H, C1~C5Alkyl,
Phenyl, C1~C3Alkyl-substituted phenyl, C1~C3Any one in alkoxy substituted phenyl.
Above-mentioned iron catalyst is any one in following compounds:
(1)[(Cy-PNHP)Fe(CO)(Br)2]
Cy represents cyclohexyl in formula；
(2)[(Ph-PNHP)Fe(CO)(Br)2]
Ph represents phenyl in formula；
(3)[(iPr-PNHP)Fe(CO)(Br)2]
IPr represents isopropyl in formula.
Above-mentioned three kinds of iron catalysts are all in accordance with document " Wei Ma.；Suya Cui.；Jianliang Xiao.；Chao
Wang.Chem.Eur.J.2018,24,13118-13123. the synthesis of method disclosed in ".
In above-mentioned synthetic method, the molar ratio of the preferably described amino alcohol and enol is 1:1~3.
In above-mentioned synthetic method, the additional amount of the triethyl group Boratex is the 5%~18% of amino alcohol mole, preferably
The additional amount of triethyl group Boratex is the 9%~12% of amino alcohol mole.
In above-mentioned synthetic method, the additional amount of the iron catalyst is the 1%~6% of amino alcohol mole, and preferably iron is urged
The additional amount of agent is the 3%~4% of amino alcohol mole.
In above-mentioned synthetic method, the alkali is potassium tert-butoxide, sodium tert-butoxide, sodium hydroxide, potassium hydroxide, cesium hydroxide
In any one, additional amount is 1~3 times of amino alcohol mole.
In above-mentioned synthetic method, the organic solvent is toluene, tetrahydrofuran, Isosorbide-5-Nitrae-dioxane, n-hexane, 1,3,5-
Any one in trimethylbenzene.
The present invention obtains pyrrolin using amino alcohol and enol as Material synthesis for the first time, is made for the first time with metallic iron cheap and easy to get
The synthesis of pyrrolin is realized by dehydrogenation coupling and carbon-carbon bond fracture for catalyst.Easy to operate, reaction condition is mild, green ring
It protects, is pollution-free, reaction substrate has good applicability, and can be carried out gram-grade reaction.
Specific embodiment
Below with reference to embodiment, the present invention is described in more detail, but protection scope of the present invention is not limited in these
Embodiment.
Embodiment 1
The following 2- of preparation structure formula (4'- aminomethyl phenyl) -1- pyrrolin
By 24 μ L (0.0225mmol) triethyl group Boratexes and 5.3mg (0.0075mmol) [(Cy-PNHP)Fe(CO)
(Br)2], 1.5mL toluene be added in reaction tube, be mixed 10 minutes, add 37.75mg (0.25mmol) 2- amino-
1- (4- aminomethyl phenyl) ethyl alcohol, 34 μ L (0.5mmol) allyl alcohols, 48mg (0.375mmol) potassium tert-butoxide, under protection of argon gas
120 DEG C are stirred to react 12 hours, are cooled to room temperature, are shifted after reaction with methylene chloride, and vacuum distillation removes methylene chloride, first
Benzene, using the volume ratio of petroleum ether and ethyl acetate for 5:1 mixed liquor as eluent, rapid column chromatography separation product obtains 2-
(4'- aminomethyl phenyl) -1- pyrrolin, yield 73%, characterize data are as follows:1H NMR(400MHz,CDCl3):δ(ppm)
7.74-7.72(d,2H),7.26-7.20(m,2H),4.06-4.03(m,2H),2.95-2.90(m,2H),2.38(s,3H),
2.06-1.98(m,2H)；13C NMR(100MHz,CDCl3):δ(ppm)173.3,140.6,132.1,129.2,127.7,
61.6,35.0,22.8,21.5；HRMS(ESI+)m/z C10H11N[M+H]+: experiment value 160.1126, theoretical value 160.1118.
Embodiment 2
The following 2- of preparation structure formula (benzo [d] [1,3] dioxa cyclopentenyl) -1- pyrrolin
In the present embodiment, is replaced and implemented with equimolar 2- amino -1- (benzo [d] [1,3] dioxa cyclopentenyl) ethyl alcohol
2- amino -1- (4- aminomethyl phenyl) ethyl alcohol in example 1, other steps are same as Example 1, obtain 2- (benzo [d] [1,3] two
Oxole base) -1- pyrrolin, yield 51%, characterize data are as follows:1H NMR(400MHz,CDCl3):δ(ppm)
7.43-7.42(d,1H),7.29-7.27(d,2H),6.83-6.81(d,1H),5.99(s,2H),4.04-4.01(t,2H),
2.91-2.86(t,2H),2.06-1.98(m,2H)；13C NMR(100MHz,CDCl3):δ(ppm)172.5,149.5,148.0,
129.4,122.7,108.0,107.5,101.5,61.4,35.1,22.9；HRMS(ESI+)m/z C10H11N[M+H]+: experiment value
190.0868 theoretical value 190.0859.
Embodiment 3
The following 2- of preparation structure formula (4'- chlorphenyl) -1- pyrrolin
In the present embodiment, with the 2- amino -1- (4- in equimolar 2- amino -1- (4- chlorphenyl) ethyl alcohol alternative embodiment 1
Aminomethyl phenyl) ethyl alcohol, other steps are same as Example 1, obtain 2- (4'- chlorphenyl) -1- pyrrolin, yield 67%,
Characterize data are as follows:1H NMR(400MHz,CDCl3):δ(ppm)7.77-7.75(d,2H),7.38-7.36(m,2H),4.07-
4.03(m,2H),2.93-2.88(m,2H),2.07-2.00(m,2H)；13C NMR(100MHz,CDCl3):δ(ppm)172.3,
136.4,133.2,129.0,128.8,61.7,35.0,22.8；HRMS(ESI+)m/zC10H11N[M+H]+: experiment value
180.0588 theoretical value 180.0580.
Embodiment 4
The following 2- of preparation structure formula (1'- naphthalene) -1- pyrrolin
In the present embodiment, with 2- amino -1- (the 4- first in equimolar 2- amino -1- (1- naphthalene) ethyl alcohol alternative embodiment 1
Base phenyl) ethyl alcohol, other steps are same as Example 1, obtain 2- (1'- naphthalene) -1- pyrrolin, yield 34%, characterization
Data are as follows:1H NMR(400MHz,CDCl3):δ(ppm)9.01-8.98(d,1H),7.90-7.86(t,2H),7.68-7.66(d,
2H),7.59-7.56(t,1H),7.53-7.46(m,1H),4.27-4.24(t,2H),3.12-3.08(t,2H),2.12-2.04
(m,2H)；13C NMR(100MHz,CDCl3):δ(ppm)174.5,134.0,132.6,131.2,130.3,128.4,127.4,
127.1,126.7,126.1,124.8,62.6,38.7,22.7；HRMS(ESI+)m/zC10H11N[M+H]+: experiment value
196.1126 theoretical value 196.1122.
Embodiment 5
The following 2- of preparation structure formula (2'- naphthalene) -1- pyrrolin
In the present embodiment, with 2- amino -1- (the 4- first in equimolar 2- amino -1- (2- naphthalene) ethyl alcohol alternative embodiment 1
Base phenyl) ethyl alcohol, other steps are same as Example 1, obtain 2- (2'- naphthalene) -1- pyrrolin, yield 56%, characterization
Data are as follows:1H NMR(400MHz,CDCl3):δ(ppm)8.16(s,1H),8.12-8.10(d,1H),7.90-7.87(m,3H),
7.54-7.49(m,2H),4.15-4.11(t,2H),3.09-3.05(t,2H),2.12-2.05(m,2H)；13C NMR
(100MHz,CDCl3):δ(ppm)173.4,134.4,133.1,132.2,128.8,128.3,128.2,127.9,127.1,
126.5,124.6,61.8,35.0,22.8；HRMS(ESI+)m/zC10H11N[M+H]+: experiment value 196.1126, theoretical value
196.1114。
Embodiment 6
The following 2- of preparation structure formula (9'- phenanthryl) -1- pyrrolin
In the present embodiment, with 2- amino -1- (the 4- first in equimolar 2- amino -1- (9- phenanthryl) ethyl alcohol alternative embodiment 1
Base phenyl) ethyl alcohol, other steps are same as Example 1, obtain 2- (9'- phenanthryl) -1- pyrrolin, yield 30%, characterization
Data are as follows:1H NMR(400MHz,CDCl3):δ(ppm)):δ(ppm)8.98-8.95(m,1H),8.74-8.67(m,2H),
7.93-7.88(m,2H),7.70-7.58(m,4H),4.29-4.25(m,2H),3.19-3.14(m,2H),2.16-2.08(m,
2H)；13C NMR(100MHz,CDCl3):δ(ppm)174.6,131.6,131.1,130.9,130.85,130.0,128.8,
127.8,127.4,127.2,126.9,126.8,122.9,122.7,62.7,39.0,22.8；HRMS(ESI+)m/z C10H11N
[M+H]+: experiment value 246.1283, theoretical value 246.1274.
Embodiment 7
The following 3- methyl -2- phenyl -1- pyrrolin of preparation structure formula
In the present embodiment, with 2- amino -1- (4- aminomethyl phenyl) ethyl alcohol in equimolar benzene glycosides amine alcohol alternative embodiment 1,
Implement the allyl alcohol in 1 with the replacement of equimolar 2- butene-1-ol, is the mixing of 10:1 with the volume ratio of petroleum ether and ethyl acetate
Liquid is eluent, and rapid column chromatography separation product, other steps are same as Example 1, obtains 3- methyl -2- phenyl -1- pyrroles
Quinoline, yield 60%, characterize data are as follows:1H NMR(400MHz,CDCl3):δ(ppm)7.83-7.81(t,2H),7.41-
7.40(d,3H),4.09-3.92(m2H),3.46-3.42(t,1H),2.30-2.20(m,1H),1.75-1.71(m,1H),
1.19-1.17(d,3H)；13C NMR(100MHz,CDCl3):δ(ppm)177.6,133.8,130.2,128.6,128.0,
59.2,41.6,32.1,18.3；HRMS(ESI+)m/z C10H11N[M+H]+: experiment value 160.1126, theoretical value 160.1120.
Embodiment 8
The following 3- propyl -2- phenyl -1- pyrrolin of preparation structure formula
In the present embodiment, with the 2- butene-1-ol in equimolar 2- hexen-1-ol alternative embodiment 7, other steps and reality
It is identical to apply example 7, obtains 3- propyl -2- phenyl -1- pyrrolin, yield 39%, characterize data are as follows:1H NMR(400MHz,
CDCl3):δ(ppm)7.80-7.78(m,2H),7.42-7.40(m,3H),4.10-4.03(m,1H),3.99-3.88(m,1H),
3.40-3.34(m,1H),2.22-2.12(m,1H),1.86-1.80(m,1H),1.42-1.26(m,4H),0.93-0.89(t,
3H)；13C NMR(100MHz,CDCl3):δ(ppm)176.7,134.3,130.2,128.6,128.0,59.8,47.2,34.4,
29.3,21.1,14.2；HRMS(ESI+)m/z C10H11N[M+H]+: experiment value 188.1439, theoretical value 188.1438.
Embodiment 9
The following 4- methyl -2- phenyl -1- pyrrolin of preparation structure formula
In the present embodiment, with the 2- butene-1-ol in equimolar methallyl alcohol alternative embodiment 7, other
Step is same as Example 7, obtains 4- methyl -2- phenyl -1- pyrrolin, yield 54%, characterize data are as follows:1H NMR
(400MHz,CDCl3):δ(ppm)7.83-7.82(m,2H),7.42-7.39(m,3H),4.20-4.15(m,1H),3.67-
3.63(m,1H),3.14-3.10(m,1H),2.60-2.53(m,2H),1.11-1.10(d,3H)；13C NMR(100MHz,
CDCl3):δ(ppm)173.0,134.8,130.5,128.5,127.7,69.0,43.3,31.6,20.5；HRMS(ESI+)m/z
C10H11N[M+H]+: experiment value 160.1126, theoretical value 160.1115.
Embodiment 9
Following 2, the 4- diphenyl -1- pyrrolin of preparation structure formula
In the present embodiment, with the 2- butene-1-ol in equimolar 2- phenyl -2- propylene -1- alcohol alternative embodiment 7, with stone
The mixed liquor that the volume ratio of oily ether and ethyl acetate is 20:1 is eluent, rapid column chromatography separation product, other steps and reality
It is identical to apply example 7, obtains 2,4- diphenyl -1- pyrrolin, yield 30%, characterize data are as follows:1HNMR(400MHz,CDCl3):
δ(ppm)7.83-7.82(m,2H),7.45-7.41(m,3H),7.32-7.29(m,2H),7.25-7.20(m,3H),4.56-
4.50(m,1H),4.15-4.10(m,1H),3.71-3.63(m,1H),3.51-3.44(m,1H),3.13-3.06(m,1H)；13C
NMR(100MHz,CDCl3):δ(ppm)172.6,145.2,134.5,130.7,128.9,128.7,127.8,127.0,
126.6,69.7,44.2,43.1；HRMS(ESI+)m/zC10H11N[M+H]+: experiment value 222.1278, theoretical value 222.1283.
Embodiment 10
The following 5- methyl -2- phenyl -1- pyrrolin of preparation structure formula
In the present embodiment, with the 2- butene-1-ol in equimolar 3- butene-2 -ol alternative embodiment 7,135 DEG C of reactions 6 are small
When, using the volume ratio of petroleum ether and ethyl acetate for 20:1 mixed liquor as eluent, rapid column chromatography separation product, other step
It is rapid same as Example 7, obtain 5- methyl -2- phenyl -1- pyrrolin, yield 49%, characterize data are as follows:1H NMR
(400MHz,CDCl3):δ(ppm)7.85-7.82(q,2H),7.41-7.37(m,3H),4.31-4.26(q,1H),3.10-
3.01(m,1H),2.93-2.84(m,1H),2.29-2.20(m,1H),1.60-1.51(m,1H),1.37-1.35(d,3H)；13C
NMR(100MHz,CDCl3):δ(ppm)171.9,134.9,130.4,128.5,127.8,68.6,35.3,30.8,22.3；
HRMS(ESI+)m/z C10H11N[M+H]+: experiment value 160.1126, theoretical value 160.1127.
Embodiment 11
The following 5- amyl -2- phenyl -1- pyrrolin of preparation structure formula
In the present embodiment, with the 2- butene-1-ol in equimolar 1-OCOL alternative embodiment 7,135 DEG C of reactions 12
Hour, using the volume ratio of petroleum ether and ethyl acetate for 20:1 mixed liquor as eluent, rapid column chromatography separation product, other
Step is same as Example 7, obtains 5- amyl -2- phenyl -1- pyrrolin, yield 50%, characterize data are as follows:1H NMR
(400MHz,CDCl3):δ(ppm)7.85-7.83(m,2H),7.41-7.39(m,3H),4.20-4.15(m,1H),3.05-
2.97(m,1H),2.92-2.83(m,1H),2.24-2.15(m,1H),1.86-1.82(m,1H),1.63-1.57(m,2H),
1.49-1.45(m,4H),0.92-0.88(t,3H)；13C NMR(100MHz,CDCl3):δ(ppm)171.8,134.9,130.3,
128.5,127.7,73.5,36.8,35.0,32.1,28.7,26.5,22.8,14.2；HRMS(ESI+)m/z C10H11N[M+H]+: it is real
Test value 216.1752, theoretical value 216.1753.
Embodiment 12
The following 2,5- diphenyl -1- pyrrolin of preparation structure formula
In the present embodiment, with the 2- butene-1-ol in equimolar 1- phenyl -2- propylene -1- alcohol alternative embodiment 7,135 DEG C
Reaction 24 hours, using the volume ratio of petroleum ether and ethyl acetate for 20:1 mixed liquor as eluent, rapid column chromatography separation produce
Object, other steps are same as Example 7, obtain 2,5- diphenyl -1- pyrrolin, yield 44%, characterize data are as follows:1H
NMR(400MHz,CDCl3):δ(ppm)7.96-7.94(d,2H),7.45-7.42(t,3H),7.35-7.29(m,4H),7.25-
7.23(d,1H),5.33-5.30(t,1H),3.21-3.14(m,1H),3.05-2.97(m,1H),2.64-2.55(m,1H),
1.95-1.86(m,1H)；13C NMR(100MHz,CDCl3):δ(ppm)173.8,144.8,134.6,130.7,128.6,
128.0,126.9,126.7,76.2,35.7,32.6；HRMS(ESI+)m/zC10H11N[M+H]+: experiment value 222.1283, it is practical
Value 222.1280.
Embodiment 13
The following 2- of preparation structure formula (4'- methoxyphenyl) -1- pyrrolin
In the present embodiment, with the 2- amino-in equimolar 2- amino -1- (4- methoxyphenyl) ethyl alcohol alternative embodiment 1
1- (4- aminomethyl phenyl) ethyl alcohol, other steps are same as Example 1, obtain 2- (4'- methoxyphenyl) -1- pyrrolin, produce
Rate is 41%, characterize data are as follows:1H NMR(400MHz,CDCl3):δ(ppm)7.79-7.77(d,2H),6.92-6.90(d,
2H),4.04-4.01(t,2H),3.83(s,3H),2.93-2.88(t,2H),2.05-1.97(m,2H)；13C NMR(100MHz,
CDCl3):δ(ppm)172.7,161.4,129.2,113.8,61.4,55.4,34.9,22.8；HRMS(ESI+)m/z C10H11N
[M+H]+: experiment value 176.1075, theoretical value 176.1073.
Embodiment 14
The following 2- of preparation structure formula (3', 5'- 3,5-dimethylphenyl) -1- pyrrolin
In the present embodiment, with the 2- ammonia in equimolar 2- amino -1- (3,5- 3,5-dimethylphenyl) ethyl alcohol alternative embodiment 1
Base -1- (4- aminomethyl phenyl) ethyl alcohol, other steps are same as Example 1, obtain 2- (3', 5'- 3,5-dimethylphenyl) -1- pyrroles
Quinoline, yield 70%, characterize data are as follows:1H NMR(400MHz,CDCl3):δ(ppm)7.46(s,2H),7.06(s,1H),
4.06-4.02(t,2H),2.94-2.89(m,2H),2.34(s,6H),2.05-1.97(m,2H)；13CNMR(100MHz,
CDCl3):δ(ppm)173.0,134.9,130.4,128.5,127.7,69.1,43.3,31.6,20.5；HRMS(ESI+)m/z
C10H11N[M+H]+: experiment value 174.1283, theoretical value 174.1274.
Embodiment 15
The following 2- of preparation structure formula (4'- aminomethyl phenyl) -1- pyrrolin
In the present embodiment, with equimolar [(iPr-PNHP)Fe(CO)(Br)2] replacement example 1 in [(Cy-PNHP)Fe
(CO)(Br)2], other steps are same as Example 1, obtain 2- (4'- aminomethyl phenyl) -1- pyrrolin, yield 71%.
Claims (9)
1. a kind of method that iron catalytic amino alcohol synthesizes pyrrolines with enol, it is characterised in that: by amino shown in Formulas I
Enol shown in alcohol and Formula II, triethyl group Boratex, iron catalyst, potassium tert-butoxide are added in organic solvent, in inert gas shielding
Lower 120~135 DEG C of reactions, isolate and purify product, obtain pyrrolines shown in formula III after fully reacting；
Ar represents phenyl, C in formula1~C4Alkyl-substituted phenyl, C1~C4Alkoxy substituted phenyl, halogenophenyl, benzo [d] [1,
3] dioxa cyclopentenyl, naphthalene, any one in phenanthryl, R1、R2、R3It is independent to represent H, C1~C5Alkyl, phenyl, C1
~C3Alkyl-substituted phenyl, C1~C3Any one in alkoxy substituted phenyl；
Above-mentioned iron catalyst is any one in following compounds:
(1)[(Cy-PNHP)Fe(CO)(Br)2]
Cy represents cyclohexyl in formula；
(2)[(Ph-PNHP)Fe(CO)(Br)2]
Ph represents phenyl in formula；
(3)[(iPr-PNHP)Fe(CO)(Br)2]
IPr represents isopropyl in formula.
2. the method that iron catalytic amino alcohol according to claim 1 synthesizes pyrrolines with enol, feature exist
In: the molar ratio of the amino alcohol and enol is 1:1~3.
3. the method that iron catalytic amino alcohol according to claim 1 synthesizes pyrrolines with enol, feature exist
In: the additional amount of the triethyl group Boratex is the 5%~18% of amino alcohol mole.
4. the method that iron catalytic amino alcohol according to claim 3 synthesizes pyrrolines with enol, feature exist
In: the additional amount of the triethyl group Boratex is the 9%~12% of amino alcohol mole.
5. the method that iron catalytic amino alcohol according to claim 1 synthesizes pyrrolines with enol, feature exist
In: the additional amount of the iron catalyst is the 1%~6% of amino alcohol mole.
6. the method that iron catalytic amino alcohol according to claim 5 synthesizes pyrrolines with enol, feature exist
In: the additional amount of the iron catalyst is the 3%~4% of amino alcohol mole.
7. the method that iron catalytic amino alcohol according to claim 1 synthesizes pyrrolines with enol, feature exist
In: the alkali be potassium tert-butoxide, sodium tert-butoxide, sodium hydroxide, potassium hydroxide, any one in cesium hydroxide.
8. the method that iron catalytic amino alcohol according to claim 7 synthesizes pyrrolines with enol, feature exist
In: the additional amount of the alkali is 1~3 times of amino alcohol mole.
9. the method that iron catalytic amino alcohol according to claim 1 synthesizes pyrrolines with enol, feature exist
In: the organic solvent be toluene, tetrahydrofuran, 1,4- dioxane, n-hexane, any one in 1,3,5- trimethylbenzene.
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| CN105829330A (en) * | 2013-12-18 | 2016-08-03 | 弗门尼舍有限公司 | Hydrogenation of esters with Fe/tridentate ligands complexes |
| CN106163662A (en) * | 2014-03-31 | 2016-11-23 | 宝洁公司 | Ester uses iron complex as the homogeneous hydrogenation of catalyst |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105829330A (en) * | 2013-12-18 | 2016-08-03 | 弗门尼舍有限公司 | Hydrogenation of esters with Fe/tridentate ligands complexes |
| CN106163662A (en) * | 2014-03-31 | 2016-11-23 | 宝洁公司 | Ester uses iron complex as the homogeneous hydrogenation of catalyst |
Non-Patent Citations (3)
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| 邹清竹: "单一催化体系下醇和胺及胺和胺的借氢反应研究", 《陕西师范大学硕士学位论文》 * |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114874119A (en) * | 2022-03-06 | 2022-08-09 | 昆明学院 | Method for photocatalytic synthesis of 3, 4-dialkyl-4-pyrroline-2-one derivative |
| CN114874119B (en) * | 2022-03-06 | 2023-06-06 | 昆明学院 | Method for synthesizing 3, 4-dialkylated-4-pyrroline-2-one derivative by photocatalysis |
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| CN109734643B (en) | 2021-05-14 |
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