CN109970524A - The preparation method and application of 1,3- bis- (3,4- alkyl phenyl) acetone - Google Patents
The preparation method and application of 1,3- bis- (3,4- alkyl phenyl) acetone Download PDFInfo
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- CN109970524A CN109970524A CN201910380462.3A CN201910380462A CN109970524A CN 109970524 A CN109970524 A CN 109970524A CN 201910380462 A CN201910380462 A CN 201910380462A CN 109970524 A CN109970524 A CN 109970524A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/455—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation with carboxylic acids or their derivatives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/135—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/10—Systems containing only non-condensed rings with a five-membered ring the ring being unsaturated
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Abstract
The invention belongs to medical science and field of photovoltaic materials, disclose the preparation method and application of 1,3- bis- (3,4- alkyl phenyl) acetone.The present invention uses two kinds of Alkyl-diol silica reaction preparation 1,3- bis- (3,4- alkyl phenyl) acetone.Operation is simple and easy, carries out under mild reaction conditions.Synthetic method provided by the invention is simple and easy, scientific and reasonable, environmentally protective, economical and practical, is suitble to large-scale production.
Description
Technical field
The invention belongs to medical science and field of photovoltaic materials, relate generally to the system of 1,3- bis- (3,4- alkyl phenyl) acetone
Preparation Method and application.
Background technique
Diphenyl acetone due to its unique molecular structure, photoelectric characteristic and their applications on p- electronic material,
Make its poromerics, crystallization photoconductor, synthesizing graphite alkene in terms of using more and more extensive.Meanwhile diphenyl
Acetone can be used as a kind of cheap precursor, relative complex structure fast and effeciently be prepared, so in terms of pharmaceutical synthesis
There is important application.Based on this, this field needs easier, green, economic method to synthesize diphenyl acetone.
Summary of the invention
For overcome the deficiencies in the prior art, the present invention provides the preparation methods of 1,3- bis- (3,4- alkyl phenyl) acetone
And application.The present invention uses two kinds of Alkyl-diol silica reaction preparation 1,3- bis- (3,4- alkyl phenyl) acetone.Operation is simple
It is easy, it carries out under mild reaction conditions.Synthetic method provided by the invention is simple and easy, scientific and reasonable, environmentally protective, economical
It is practical, it is suitble to large-scale production.
Above-mentioned purpose of the invention is achieved through the following technical solutions:
The preparation method of one kind 1,3- bis- (3,4- alkyl phenyl) acetone, using two kinds of Alkyl-diol silicas as raw material, with DMAP
For catalyst, DCC is dehydrating agent, is chemically reacted in organic solvent, finally obtains 1,3- bis- (3,4- alkyl phenyl) third
Ketone has the structure as shown in general formula (I):
Wherein, R1With R2For identical-CH3；
Two kinds of Alkyl-diol silicas are respectively to methylphenyl acetic acid, m-Tolylacetic acid；
Described is 1:1 to methylphenyl acetic acid and m-Tolylacetic acid molar ratio；
The molar ratio to methylphenyl acetic acid and DCC is 1~3:4~6, to the molar ratio of methylphenyl acetic acid and DMAP
For 2~4:1~2；
The organic solvent is dry methylene chloride；
Dry methylene chloride refers to the methylene chloride after removing water, operates as follows, it may be assumed that methylene chloride is added in flask
And calcium hydride, distillation obtains dry methylene chloride at 60 DEG C.
The molar ratio to methylphenyl acetic acid and dry methylene chloride is 1:40~80；Methylbenzene second between described
The molar ratio of acid and dry methylene chloride is 1:90~130；
Described is to methylphenyl acetic acid
The m-Tolylacetic acid is
Wherein R3With R4For-CH3。
Specific step is as follows for preparation method:
S1. it is added in round-bottomed flask by DCC, DMAP and to methylphenyl acetic acid, and dry methylene chloride stirring is added
Uniformly；
S2. m-Tolylacetic acid is dissolved in and is slowly added dropwise in dichloromethane solution into the reaction solution of step S1,20~
30 DEG C of reaction 24-72h；
S3. it is filtered to remove the precipitating of step S2, obtains (3, the 4- alkylbenzenes of 1,3- bis- with column Chromatographic purification after filtrate revolving
Base) acetone.
Further, the eluant, eluent in the step S3 column chromatography is petroleum ether.
Further, dry with anhydrous sodium sulfate before the filtrate revolving in the step 3.
Further, the dropwise addition mode of the step S2 is constant pressure funnel dropwise addition.
The DCC is dicyclohexylcarbodiimide, and the DMAP is dimethylamino naphthyridine.
1,3- bis- made from preparation method of the present invention (3,4- alkyl phenyl) acetone is in medicine preparation and field of photovoltaic materials
On application.
Such as it is used for antidiabetic drugOr photoelectricity crystallizes conductor materialPreparation.
Compared with the prior art, the invention has the advantages that:
The present invention uses two kinds alkyl-substituted to prepare (the 3,4- alkyl of 1,3- bis- to phenylacetic acid and isophthalic acetic acidreaction for the first time
Phenyl) acetone；Operation is simple and easy, is not necessarily to nitrogen protection, can carry out under mild reaction conditions.It is provided by the invention
Synthetic method reaction yield is high, and preparation process is simple, not will cause environmental pollution.Synthetic method provided by the invention is to report for the first time
Road, simple and easy, scientific and reasonable, economical and practical, suitable large-scale production.
Specific embodiment
The present invention is described in detail below by specific embodiment, but is not limited the scope of the invention.Unless otherwise specified, originally
Experimental method used by inventing is conventional method, and experiment equipment used, material, reagent etc. can chemically company be bought.
Embodiment 1
A 100mL round-bottomed flask is taken, by DCC (1.0320g, 5mmol), DMAP (0.1527g, 1.25mmol) and 4- first
Base phenylacetic acid (0.3754g, 2.5mmol) is added in the dry methylene chloride of 10mL, stirs at 20 DEG C to whole dissolutions.By 3-
Methylphenyl acetic acid (0.3754g, 2.5mmol) is dissolved in the dry methylene chloride of 20mL, then slow with constant pressure funnel
It is added dropwise in above-mentioned solution.Stirring for 24 hours, is spin-dried for, then through pillar layer separation, eluant, eluent is petroleum ether, to obtain targeted
Close object.
It is characterized as below:
1,3- bis- (3,4- aminomethyl phenyl) acetone: yield: 68%.1H NMR(500MHz,CDCl3) δ 7.23 (dd, J=
10.4,5.2Hz, 1H), 7.15 (d, J=7.8Hz, 2H), 7.08 (dd, J=17.2,7.8Hz, 3H), 6.98 (d, J=6.0Hz,
2H), 3.70 (d, J=1.6Hz, 2H), 3.69 (d, J=2.1Hz, 2H), 2.36 (s, 3H), 2.35 (s, 3H)
Embodiment 2
A 100mL round-bottomed flask is taken, by DCC (1.0320g, 5mmol), DMAP (0.1527g, 1.25mmol) and 4- first
Base phenylacetic acid (0.3754g, 2.5mmol) is added in the dry methylene chloride of 10mL, stirs at 25 DEG C to whole dissolutions.By 3-
Methylphenyl acetic acid (0.3754g, 2.5mmol) is dissolved in the dry methylene chloride of 20mL, then slow with constant pressure funnel
It is added dropwise in above-mentioned solution.Stirring for 24 hours, is spin-dried for, then through pillar layer separation, eluant, eluent is petroleum ether, to obtain targeted
Close object.
It is characterized as below:
1,3- bis- (3,4- aminomethyl phenyl) acetone: yield: 60%.1H NMR(500MHz,CDCl3) δ 7.23 (dd, J=
10.4,5.2Hz, 1H), 7.15 (d, J=7.8Hz, 2H), 7.08 (dd, J=17.2,7.8Hz, 3H), 6.98 (d, J=6.0Hz,
2H), 3.70 (d, J=1.6Hz, 2H), 3.69 (d, J=2.1Hz, 2H), 2.36 (s, 3H), 2.35 (s, 3H)
Embodiment 3
A 100mL round-bottomed flask is taken, by DCC (1.0320g, 5mmol), DMAP (0.1527g, 1.25mmol) and 4- first
Base phenylacetic acid (0.3754g, 2.5mmol) is added in the dry methylene chloride of 10mL, stirs at 30 DEG C to whole dissolutions.By 3-
Methylphenyl acetic acid (0.3754g, 2.5mmol) is dissolved in the dry methylene chloride of 20mL, then slow with constant pressure funnel
It is added dropwise in above-mentioned solution.Stirring for 24 hours, is spin-dried for, then through pillar layer separation, eluant, eluent is petroleum ether, to obtain targeted
Close object.
It is characterized as below:
1,3- bis- (3,4- aminomethyl phenyl) acetone: yield: 56%.1H NMR(500MHz,CDCl3) δ 7.23 (dd, J=
10.4,5.2Hz, 1H), 7.15 (d, J=7.8Hz, 2H), 7.08 (dd, J=17.2,7.8Hz, 3H), 6.98 (d, J=6.0Hz,
2H), 3.70 (d, J=1.6Hz, 2H), 3.69 (d, J=2.1Hz, 2H), 2.36 (s, 3H), 2.35 (s, 3H)
Embodiment 4
A 100mL round-bottomed flask is taken, by DCC (1.0320g, 5mmol), DMAP (0.1527g, 1.25mmol) and 4- first
Base phenylacetic acid (0.3754g, 2.5mmol) is added in the dry methylene chloride of 10mL, stirs at 20 DEG C to whole dissolutions.By 3-
Methylphenyl acetic acid (0.3754g, 2.5mmol) is dissolved in the dry methylene chloride of 20mL, then slow with constant pressure funnel
It is added dropwise in above-mentioned solution.48h is stirred, is spin-dried for, then through pillar layer separation, eluant, eluent is petroleum ether, to obtain targeted
Close object.
It is characterized as below:
1,3- bis- (3,4- aminomethyl phenyl) acetone: yield: 55%.1H NMR(500MHz,CDCl3) δ 7.23 (dd, J=
10.4,5.2Hz, 1H), 7.15 (d, J=7.8Hz, 2H), 7.08 (dd, J=17.2,7.8Hz, 3H), 6.98 (d, J=6.0Hz,
2H), 3.70 (d, J=1.6Hz, 2H), 3.69 (d, J=2.1Hz, 2H), 2.36 (s, 3H), 2.35 (s, 3H)
Embodiment 5
A 100mL round-bottomed flask is taken, by DCC (1.0320g, 5mmol), DMAP (0.1527g, 1.25mmol) and 4- first
Base phenylacetic acid (0.3754g, 2.5mmol) is added in the dry methylene chloride of 10mL, stirs at 20 DEG C to whole dissolutions.By 3-
Methylphenyl acetic acid (0.3754g, 2.5mmol) is dissolved in the dry methylene chloride of 20mL, then slow with constant pressure funnel
It is added dropwise in above-mentioned solution.72h is stirred, is spin-dried for, then through pillar layer separation, eluant, eluent is petroleum ether, to obtain targeted
Close object.
It is characterized as below:
1,3- bis- (3,4- aminomethyl phenyl) acetone: yield: 48%.1H NMR(500MHz,CDCl3) δ 7.23 (dd, J=
10.4,5.2Hz, 1H), 7.15 (d, J=7.8Hz, 2H), 7.08 (dd, J=17.2,7.8Hz, 3H), 6.98 (d, J=6.0Hz,
2H), 3.70 (d, J=1.6Hz, 2H), 3.69 (d, J=2.1Hz, 2H), 2.36 (s, 3H), 2.35 (s, 3H)
Embodiment 6
A 100mL round-bottomed flask is taken, by DCC (0.8247g, 4mmol), DMAP (0.1466g, 1.2mmol) and 4- first
Base phenylacetic acid (0.3754g, 2.5mmol) is added in the dry methylene chloride of 8mL, stirs at 20 DEG C to whole dissolutions.By 3-
Methylphenyl acetic acid (0.3754g, 2.5mmol) is dissolved in the dry methylene chloride of 18mL, then slow with constant pressure funnel
It is added dropwise in above-mentioned solution.Stirring for 24 hours, is spin-dried for, then through pillar layer separation, eluant, eluent is petroleum ether, to obtain targeted
Close object.
It is characterized as below:
1,3- bis- (3,4- aminomethyl phenyl) acetone: yield: 52%.1H NMR(500MHz,CDCl3) δ 7.23 (dd, J=
10.4,5.2Hz, 1H), 7.15 (d, J=7.8Hz, 2H), 7.08 (dd, J=17.2,7.8Hz, 3H), 6.98 (d, J=6.0Hz,
2H), 3.70 (d, J=1.6Hz, 2H), 3.69 (d, J=2.1Hz, 2H), 2.36 (s, 3H), 2.35 (s, 3H)
Embodiment 7
A 100mL round-bottomed flask is taken, by DCC (1.2371g, 6mmol), DMAP (0.2443g, 2mmol) and 4- methyl
Phenylacetic acid (0.5256g, 3.5mmol) is added in the dry methylene chloride of 12mL, stirs at 20 DEG C to whole dissolutions.By 3- first
Base phenylacetic acid (0.5256g, 3.5mmol) is dissolved in the dry methylene chloride of 24mL, is then slowly dripped with constant pressure funnel
It adds in above-mentioned solution.Stirring for 24 hours, is spin-dried for, then through pillar layer separation, eluant, eluent is petroleum ether, to obtain target chemical combination
Object.
It is characterized as below:
1,3- bis- (3,4- aminomethyl phenyl) acetone: yield: 58%.1H NMR(500MHz,CDCl3) δ 7.23 (dd, J=
10.4,5.2Hz, 1H), 7.15 (d, J=7.8Hz, 2H), 7.08 (dd, J=17.2,7.8Hz, 3H), 6.98 (d, J=6.0Hz,
2H), 3.70 (d, J=1.6Hz, 2H), 3.69 (d, J=2.1Hz, 2H), 2.36 (s, 3H), 2.35 (s, 3H)
Embodiment 8
A 250mL round-bottomed flask is taken, by DCC (2.0618g, 10mmol), DMAP (0.3665g, 3mmol) and 4- methyl
Phenylacetic acid (0.9011g, 6mmol) is added in the dry methylene chloride of 25mL, stirs at 20 DEG C to whole dissolutions.By 3- methyl
Phenylacetic acid (0.9011g, 6mmol) is dissolved in the dry methylene chloride of 50mL, then with constant pressure funnel be slowly added dropwise to
In above-mentioned solution.Stirring for 24 hours, is spin-dried for, then through pillar layer separation, eluant, eluent is petroleum ether, to obtain target compound.
It is characterized as below:
1,3- bis- (3,4- aminomethyl phenyl) acetone: yield: 62%.1H NMR(500MHz,CDCl3) δ 7.23 (dd, J=
10.4,5.2Hz, 1H), 7.15 (d, J=7.8Hz, 2H), 7.08 (dd, J=17.2,7.8Hz, 3H), 6.98 (d, J=6.0Hz,
2H), 3.70 (d, J=1.6Hz, 2H), 3.69 (d, J=2.1Hz, 2H), 2.36 (s, 3H), 2.35 (s, 3H)
Embodiment 9
A 250mL round-bottomed flask is taken, by DCC (4.1236g, 20mmol), DMAP (0.7330g, 6mmol) and 4- methyl
Phenylacetic acid (1.8022g, 12mmol) is added in the dry methylene chloride of 30mL, stirs at 20 DEG C to whole dissolutions.By 3- first
Base phenylacetic acid (1.8022g, 12mmol) is dissolved in the dry methylene chloride of 75mL, is then slowly added dropwise with constant pressure funnel
To in above-mentioned solution.Stirring for 24 hours, is spin-dried for, then through pillar layer separation, eluant, eluent is petroleum ether, to obtain target compound.
It is characterized as below:
1,3- bis- (3,4- aminomethyl phenyl) acetone: yield: 65%.1H NMR(500MHz,CDCl3) δ 7.23 (dd, J=
10.4,5.2Hz, 1H), 7.15 (d, J=7.8Hz, 2H), 7.08 (dd, J=17.2,7.8Hz, 3H), 6.98 (d, J=6.0Hz,
2H), 3.70 (d, J=1.6Hz, 2H), 3.69 (d, J=2.1Hz, 2H), 2.36 (s, 3H), 2.35 (s, 3H)
In above 9 implementation cases column, case study on implementation 1 has obtained highest 1,3- bis- (3, the 4- aminomethyl phenyl) acetone of yield.
The preferable specific embodiment of the above, only the invention, but the protection scope of the invention is not
It is confined to this, anyone skilled in the art is in the technical scope that the invention discloses, according to the present invention
The technical solution of creation and its inventive concept are subject to equivalent substitution or change, should all cover the invention protection scope it
It is interior.
Claims (7)
1. one kind 1, the preparation method of 3- bis- (3,4- alkyl phenyl) acetone, characterized in that
Using two kinds of Alkyl-diol silicas as raw material, using DMAP as catalyst, DCC is dehydrating agent, and it is anti-that chemistry occurs in organic solvent
It answers, finally obtains 1,3- bis- (3,4- alkyl phenyl) acetone；
Two kinds of Alkyl-diol silicas are respectively to methylphenyl acetic acid, m-Tolylacetic acid；
Described is 1:1 to methylphenyl acetic acid and m-Tolylacetic acid molar ratio；
The molar ratio to methylphenyl acetic acid and DCC is 1~3:4~6, and the molar ratio to methylphenyl acetic acid and DMAP is 2
~4:1~2.
2. the preparation method of one kind 1,3- bis- (3,4- alkyl phenyl) acetone as described in claim 1, characterized in that
The organic solvent is dry methylene chloride；
The molar ratio to methylphenyl acetic acid and dry methylene chloride is 1:40~80；The m-Tolylacetic acid with
The molar ratio of dry methylene chloride is 1:90~130.
3. the preparation method of one kind 1,3- bis- (3,4- alkyl phenyl) acetone as claimed in claim 2, characterized in that
Specific step is as follows for preparation method:
S1. it is added in round-bottomed flask by DCC, DMAP and to methylphenyl acetic acid, and dry methylene chloride is added and stirs evenly；
S2. m-Tolylacetic acid is dissolved in and is slowly added dropwise in dichloromethane solution into the reaction solution of step S1,20~30 DEG C
React 24-72h；
S3. it is filtered to remove the precipitating of step S2, obtains 1,3- bis- (3,4- alkyl phenyl) third with column Chromatographic purification after filtrate revolving
Ketone.
4. the preparation method of one kind 1,3- bis- (3,4- alkyl phenyl) acetone as claimed in claim 3, characterized in that the step
Eluant, eluent in rapid S3 column chromatography is petroleum ether.
5. the preparation method of one kind 1,3- bis- (3,4- alkyl phenyl) acetone as claimed in claim 3, characterized in that the step
It is dry with anhydrous sodium sulfate before filtrate revolving in rapid 3.
6. the preparation method of one kind 1,3- bis- (3,4- alkyl phenyl) acetone as claimed in claim 3, characterized in that the step
The dropwise addition mode of rapid S2 is constant pressure funnel dropwise addition.
7. a kind of 1,3- bis- (3,4- alkyl phenyl) acetone of preparation method preparation as described in claim 1 is in antidiabetic drug and light
The application of electrocrystallization conductor material preparation aspect.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108358767A (en) * | 2018-03-15 | 2018-08-03 | 吉林大学 | The double fluorine monomers of methylbenzene containing pentaphene, preparation method and its application in poly(aryl ether ketone) functional membrane |
| CN108752249A (en) * | 2018-04-25 | 2018-11-06 | 华南理工大学 | A kind of spatial conjugation organic molecule and its preparation and application based on six aryl benzene skeletons |
-
2019
- 2019-05-08 CN CN201910380462.3A patent/CN109970524A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108358767A (en) * | 2018-03-15 | 2018-08-03 | 吉林大学 | The double fluorine monomers of methylbenzene containing pentaphene, preparation method and its application in poly(aryl ether ketone) functional membrane |
| CN108752249A (en) * | 2018-04-25 | 2018-11-06 | 华南理工大学 | A kind of spatial conjugation organic molecule and its preparation and application based on six aryl benzene skeletons |
Non-Patent Citations (4)
| Title |
|---|
| SANDRA KURJATSCHIJ等: "Synthesis and structures of crystalline solvates formed of pyridinium N-phenoxide (Reichardt’s-type) betaine dyes and alcohols", 《NEW J. CHEM.》 * |
| SUMITA BHANDARI等: "A NOVEL SYNTHESIS OF BISBENZYL KETONES BY DCC INDUCED", 《SYNTHETIC COMMUNICATIONS》 * |
| SUNIL VARUGHESE等: "Solid State Conformational Preferences of a Flexible Molecular Backbone Derived from Acetone: Dependence on Electron Donating/Withdrawing Ability of Substitutions", 《CRYSTAL GROWTH & DESIGN》 * |
| YOSHIHIRO KIKUZAWA等: "Synthesis of 2,5,8,11,14,17-Hexafluoro-hexa-perihexabenzocoronene Field-Effect Transistors", 《ORGANIC LETTERS》 * |
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