PL406275A1 - Chiral polyampholyte derivatives of dimethylphosphinic acid, polyalkylene polyamines and leucine, isoleucine or norleucine and the method of their preparation - Google Patents
Chiral polyampholyte derivatives of dimethylphosphinic acid, polyalkylene polyamines and leucine, isoleucine or norleucine and the method of their preparationInfo
- Publication number
- PL406275A1 PL406275A1 PL406275A PL40627513A PL406275A1 PL 406275 A1 PL406275 A1 PL 406275A1 PL 406275 A PL406275 A PL 406275A PL 40627513 A PL40627513 A PL 40627513A PL 406275 A1 PL406275 A1 PL 406275A1
- Authority
- PL
- Poland
- Prior art keywords
- leucine
- norleucine
- isoleucine
- acid
- chiral
- Prior art date
Links
- 229920001281 polyalkylene Polymers 0.000 title abstract 7
- 229920000768 polyamine Polymers 0.000 title abstract 7
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 title abstract 6
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 title abstract 6
- LRQKBLKVPFOOQJ-YFKPBYRVSA-N L-norleucine Chemical compound CCCC[C@H]([NH3+])C([O-])=O LRQKBLKVPFOOQJ-YFKPBYRVSA-N 0.000 title abstract 6
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 title abstract 6
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 title abstract 6
- 229960000310 isoleucine Drugs 0.000 title abstract 6
- GOJNABIZVJCYFL-UHFFFAOYSA-N dimethylphosphinic acid Chemical class CP(C)(O)=O GOJNABIZVJCYFL-UHFFFAOYSA-N 0.000 title abstract 5
- 238000000034 method Methods 0.000 title abstract 2
- 239000012634 fragment Substances 0.000 abstract 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 6
- OTBHHUPVCYLGQO-UHFFFAOYSA-N 1,7-diamino-4-aza-heptane Natural products NCCCNCCCN OTBHHUPVCYLGQO-UHFFFAOYSA-N 0.000 abstract 2
- 239000007848 Bronsted acid Substances 0.000 abstract 2
- 239000012190 activator Substances 0.000 abstract 2
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 abstract 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 abstract 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 abstract 2
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 abstract 1
- JZUHIOJYCPIVLQ-UHFFFAOYSA-N 2-methylpentane-1,5-diamine Chemical compound NCC(C)CCCN JZUHIOJYCPIVLQ-UHFFFAOYSA-N 0.000 abstract 1
- RXFCIXRFAJRBSG-UHFFFAOYSA-N 3,2,3-tetramine Chemical compound NCCCNCCNCCCN RXFCIXRFAJRBSG-UHFFFAOYSA-N 0.000 abstract 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 abstract 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 abstract 1
- OHWRASKXEUIFFB-UHFFFAOYSA-N NCP(O)=O Chemical class NCP(O)=O OHWRASKXEUIFFB-UHFFFAOYSA-N 0.000 abstract 1
- 239000005700 Putrescine Substances 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- MRNZSTMRDWRNNR-UHFFFAOYSA-N bis(hexamethylene)triamine Chemical compound NCCCCCCNCCCCCCN MRNZSTMRDWRNNR-UHFFFAOYSA-N 0.000 abstract 1
- 238000004132 cross linking Methods 0.000 abstract 1
- SSJXIUAHEKJCMH-UHFFFAOYSA-N cyclohexane-1,2-diamine Chemical compound NC1CCCCC1N SSJXIUAHEKJCMH-UHFFFAOYSA-N 0.000 abstract 1
- 239000002638 heterogeneous catalyst Substances 0.000 abstract 1
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 abstract 1
- 239000002815 homogeneous catalyst Substances 0.000 abstract 1
- 125000001909 leucine group Chemical group [H]N(*)C(C(*)=O)C([H])([H])C(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- DTSDBGVDESRKKD-UHFFFAOYSA-N n'-(2-aminoethyl)propane-1,3-diamine Chemical compound NCCCNCCN DTSDBGVDESRKKD-UHFFFAOYSA-N 0.000 abstract 1
- LSHROXHEILXKHM-UHFFFAOYSA-N n'-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCN LSHROXHEILXKHM-UHFFFAOYSA-N 0.000 abstract 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 abstract 1
- 239000012451 post-reaction mixture Substances 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 239000000758 substrate Substances 0.000 abstract 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Wynalazek dotyczy chiralnych poliamfolitów pochodnych kwasu dimetylofosfinowego, polialkilenopoliamin i leucyny, izoleucyny lub norleucyny, które są przeznaczone do stosowania jako enancjoselektory i diastereoselektory, oraz kompleksony do wytwarzania chiralnych katalizatorów homogennych i heterogennych, przedstawionych wzorem ogólnym I. Wynalazek dotyczy również sposobu wytwarzania chiralnych poliamfolitów pochodnych kwasu dimetylofosfinowego, polialkilenopoliamin i leucyny, izoleucyny lub norleucyny, przedstawionych wzorem ogólnym I, w którym A oznacza fragment struktury kwasu dimetylofosfinowego, x oznacza liczbę takich fragmentów w poliamfolicie, natomiast B oznacza fragment struktury polialkilenopoliaminy, w którym n i p mogą być takie same lub różne i oznaczają liczby całkowite od 2 do 12, natomiast q jest liczbą struktur aminopolialkenowych i wynosi od 2 do 6, y oznacza liczbę fragmentów poliaminopolialkenowych w polimerze, natomiast C oznacza fragment struktury leucyny, a z oznacza liczbę takich fragmentów w poliamfolicie, który polega na tym, że w pierwszym etapie jedną część molową kwasu fosfinowego poddaje się reakcji z co najmniej jedną częścią molową formaldehydu i co najmniej dwiema częściami molowymi grup -NH-, na które składa się suma grup -NH- pochodzących od polialkilenopoliaminy wybranej z grupy obejmującej bis(heksametyleno)triaminę, dietylenotriaminę, N-(3-aminopropylo)-1,3-diaminopropan, N-(2-aminoetylo)-1,3-diaminopropan, N,N'-bis(3-aminopropylo)etylenodiaminę, trietylenotetraminę, tetraetylenopentaminę, pentaetylenoheksaminę, 1,2-diaminoetan, 1,3-diaminopropan, 1,4-diaminobutan, 1,5-diaminopentan, 1,6-diaminoheksan, 2-metylo-1,5-diaminopentan i 1,2-diaminocykloheksan i grup -NH- pochodzących od leucyny, izoleucyny lub norleucyny, a reakcję prowadzi się w temperaturze 273-373 K, w wodzie, w obecności aktywatora w postaci dowolnego kwasu Bronsteda, aż do przereagowania substratów i utworzenia się mieszaniny kwasów aminometylofosfinowych, pochodnych polialkilenopoliamin i leucyny, izoleucyny lub norleucyny, którą w drugim etapie poddaje się usieciowaniu co najmniej jedną częścią molową formaldehydu w obecności aktywatora w postaci dowolnego kwasu Bronsteda aż do przereagowania substratów i utworzenia się chiralnego poliamfolitu zawierającego fragmenty strukturalne kwasu dimetylofosfinowego, polialkilenopoliaminy i leucyny, izoleucyny lub norleucyny, który w trzecim etapie poddaje się dosieciowaniu co najmniej 0,5 części molowej formaldehydu, po czym tak otrzymany chiralny poliamfolit wydziela się z mieszaniny poreakcyjnej.The invention relates to chiral polyampholytes derivatives of dimethylphosphinic acid, polyalkylene polyamines and leucine, isoleucine or norleucine, which are intended for use as enantioselectors and diastereoselectors, and complexes for the preparation of chiral homogeneous and heterogeneous catalysts, represented by the general formula I. The invention also relates to a method for preparing chiral polyampholytes of acid derivatives. dimethylphosphinic acid, polyalkylene polyamines and leucine, isoleucine or norleucine, represented by the general formula I, in which A is a fragment of the structure of dimethylphosphinic acid, x is the number of such fragments in the polyampholyte, and B is a fragment of the polyalkylene polyamine structure, where n and p may be the same or different and mean integers from 2 to 12, while q is the number of aminopolyalkene structures and ranges from 2 to 6, y means the number of polyaminopolyalkene fragments in the polymer, while C means a fragment of the leucine structure, and z means the number of such fragments in the polyampholyte, which means that in in the first step, one mole part of phosphinic acid is reacted with at least one mole part of formaldehyde and at least two mole parts of -NH- groups, which consist of the sum of -NH- groups derived from a polyalkylene polyamine selected from the group consisting of bis(hexamethylene)triamine, diethylenetriamine, N-(3-aminopropyl)-1,3-diaminopropane, N-(2-aminoethyl)-1,3-diaminopropane, N,N'-bis(3-aminopropyl)ethylenediamine, triethylenetetramine, tetraethylenepentamine, pentaethylenehexamine, 1 ,2-diaminoethane, 1,3-diaminopropane, 1,4-diaminobutane, 1,5-diaminopentane, 1,6-diaminohexane, 2-methyl-1,5-diaminopentane and 1,2-diaminocyclohexane and -NH- groups derived from leucine, isoleucine or norleucine, and the reaction is carried out at a temperature of 273-373 K, in water, in the presence of an activator in the form of any Bronsted acid, until the reactants are reacted and a mixture of aminomethylphosphinic acids, polyalkylene polyamine derivatives and leucine, isoleucine or norleucine is formed, which, in the second step, is cross-linked with at least one mole of formaldehyde in the presence of an activator in the form of any Bronsted acid until the substrates are reacted and a chiral polyampholyte is formed containing structural fragments of dimethylphosphinic acid, polyalkylene polyamine and leucine, isoleucine or norleucine, which in the third step is subjected to cross-linking with at least 0.5 mole of formaldehyde, after which the chiral polyampholyte thus obtained is separated from the post-reaction mixture.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL406275A PL221472B1 (en) | 2013-11-27 | 2013-11-27 | Chiral polymapholyte derivatives of dimethylphosphinic acid, leucine, isoleucine or norleucine and polyalkylene polyamines and a process for their preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL406275A PL221472B1 (en) | 2013-11-27 | 2013-11-27 | Chiral polymapholyte derivatives of dimethylphosphinic acid, leucine, isoleucine or norleucine and polyalkylene polyamines and a process for their preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL406275A1 true PL406275A1 (en) | 2014-07-07 |
| PL221472B1 PL221472B1 (en) | 2016-04-29 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL406275A PL221472B1 (en) | 2013-11-27 | 2013-11-27 | Chiral polymapholyte derivatives of dimethylphosphinic acid, leucine, isoleucine or norleucine and polyalkylene polyamines and a process for their preparation |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL221472B1 (en) |
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2013
- 2013-11-27 PL PL406275A patent/PL221472B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL221472B1 (en) | 2016-04-29 |
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