CN104910108A - 3-alkyl furoate perfume preparation method - Google Patents
3-alkyl furoate perfume preparation method Download PDFInfo
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- CN104910108A CN104910108A CN201510212713.9A CN201510212713A CN104910108A CN 104910108 A CN104910108 A CN 104910108A CN 201510212713 A CN201510212713 A CN 201510212713A CN 104910108 A CN104910108 A CN 104910108A
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- alkyl
- follicuitis
- pityrosporum
- preparation
- furan
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
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- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Furan Compounds (AREA)
Abstract
The present invention belongs to the technical field of chemical industry, and discloses a 3-alkyl furoate perfume preparation method including the following steps: halogenated furan, halogenated hydrocarbon, a ligand, a transition metal catalyst, an alcohol compound and an alkali are added into an organic solvent, CO gas is filled for reflux reaction for 1 to 60 hours at 0-140 DEG C, and a 3-alkyl furoate perfume is obtained by post-processing. The preparation method is simple, easy to operate, and low in cost, and has a market advantage; at the same time, through the yield of the perfume prepared by the method is higher.
Description
Technical field
The invention belongs to the technical field of chemical industry, relate to a kind of preparation method of spices, particularly a kind of preparation method of 3-alkyl Pityrosporum follicuitis.
Background technology
Furans spices refers to the class flavor compounds containing furan nucleus in molecule, and furans, also known as oxa-ring, is a kind of five-ring, and ring has an oxygen heteroatom, therefore furans spices belongs to heterocyclic flavor compounds.As far back as earlier 1900s, people have identified the existence of furans flavor compounds from natural food, this compounds is extensively present in the natural foods such as fish, meat, bake, vegetables, coffee, seasonings, fruit, caramel, cocoa, drinks, and plays a part key to the characteristic chicken flavor of these natural foods.Current furans spices has developed into the important spices of a class, have developed the furans spices of the various odor type such as fragrant, the fried perfume of baking, seafood is fragrant, meat is fragrant, fruital, kind quantity reaches kind more than 100, is widely used in the allotment of various food flavor(ing) and perfume compound for cosmetics.
In furans spices kind, Pityrosporum follicuitis occupies important position, and their fragrance is unique, both can make sweetener, can be used as again modifier and in various perfume formulation.Wherein 3-be the Pityrosporum follicuitis that replaces of alkyl because its synthetic route is long, production cost is high, and its fragrance Evaluation and application relevant is restricted.It is raw material that such compou nd synthesis general needs with furfural, carries out aldehyde radical protection, the α position protection of the other end, alkylation, then the step such as two deprotections, and route is tediously long, and condition is harsh, and cost is high.Therefore new synthesis technique is developed extremely urgent.
Summary of the invention
In order to overcome the shortcoming and defect of prior art, the object of the present invention is to provide a kind of preparation method of 3-alkyl Pityrosporum follicuitis.
Object of the present invention is achieved through the following technical solutions:
A preparation method for 3-alkyl Pityrosporum follicuitis, specifically comprises the following steps:
(1) by halo-furan
halohydrocarbon (R
1y), part, transition-metal catalyst, alcohol compound (R
2oH) and alkali add in organic solvent, be filled with CO gas, back flow reaction 1-60 hour at 0 DEG C ~ 140 DEG C temperature, aftertreatment obtains 3-alkyl Pityrosporum follicuitis.
The structural formula of described halo-furan is
wherein X=I, Br;
The structural formula of described halohydrocarbon is as follows:
R
1y, wherein Y=Cl, Br, I; R
1for C
1-6aliphatic saturated hydrocarbon or C
2-6unsaturated alkyl; R
1be preferably C
1-6aliphatic saturated hydrocarbon, is more preferably CH
3, CH
3cH
2, (CH
3)
2cH, CH
3cH
2cH
2, CH
3cH
2cH
2cH
2, (CH
3)
2cHCH
2, (CH
3)
3c, CH
3(CH
2)
3cH
2, CH
3cH
2cH (CH
3) or CH
3cH
2cH (CH
3) CH
2cH
2.
Described alcohol compound structural formula is as follows:
R
2oH, R
2for C
1-6aliphatic saturated hydrocarbon or C
2-8unsaturated alkyl; Described R
2be preferably C
1-6aliphatic saturated hydrocarbon, is more preferably CH
3, CH
3cH
2, (CH
3)
2cH, CH
3cH
2cH
2, CH
3cH
2cH
2cH
2, (CH
3)
2cHCH
2or (CH
3)
3c.
The structural formula of described 3-alkyl Pityrosporum follicuitis is as follows:
Wherein, R
1for C
1-6aliphatic saturated hydrocarbon or C
2-6unsaturated alkyl; R
2for C
1-6aliphatic saturated hydrocarbon or C
2-8unsaturated alkyl.
Described 3-alkyl Pityrosporum follicuitis is preferably:
Described 3-alkyl Pityrosporum follicuitis is preferably:
The normal atmosphere of the described CO of being filled with is 1-10 standard atmospheric pressure.
Described organic solvent is methyl alcohol, ethanol, Virahol, the trimethyl carbinol, methylene dichloride, chloroform, 1,2-ethylene dichloride, toluene, dimethylbenzene, tetrahydrofuran (THF), 1,4-dioxane, more than one in glycol dimethyl ether, dimethyl formamide (DMF) or dimethyl sulfoxide (DMSO) (DMSO).
Described transition-metal catalyst is Pd (OAc)
2, PdCl
2, PdBr
2, Pd (CH
3cN)
2cl
2, Pd (PPh
3)
4or Pd
2(dba)
3in more than one.
Described part is
(own-2-alkene of two rings [2.1.1]),
(two rings [2.1.1] hept-2-ene"),
(two rings [2.1.1] oct-2-ene),
(two rings [2.2.1] heptan-2,5-diene,
(pungent-2, the 5-diene of two rings [2.2.2]) or
more than one in (two rings [3.2.1]-6-in ninth of the ten Heavenly Stems alkene).
Described alkali is more than one in triethylamine, imidazoles, pyridine, DMAP, salt of wormwood, sodium carbonate, cesium carbonate, potassiumphosphate, sodium sulfate, saleratus, sodium hydroxide, potassium hydroxide, cesium hydroxide, sodium hydride, sodium tert-butoxide, potassium tert.-butoxide or trimethyl carbinol lithium.
Described halo-furan
with halohydrocarbon (R
1y) mol ratio is (100:1) ~ (1:100); Described halo-furan
with alcohol compound (R
2oH) mol ratio is (100:1) ~ (1:100); Described halo-furan
be (100:1) ~ (1:100) with the mol ratio of transition-metal catalyst.
Described halo-furan
be (100:1) ~ (1:100) with the mol ratio of part, described halo-furan
be (100:1) ~ (1:100) with the mol ratio of alkali.
Described halohydrocarbon is 1mol:(50-80 with the molecular volume ratio of organic solvent) mL.
Compared with prior art, tool of the present invention has the following advantages:
The present invention adopts one pot process 3-alkyl Pityrosporum follicuitis, and preparation method is simple, easy handling, and cost is low, have the market advantage; The spices yield simultaneously prepared by preparation method of the present invention is also higher.
Embodiment
Do specifically to describe in detail further to the present invention below in conjunction with specific embodiment, but embodiments of the present invention are not limited thereto.
Embodiment 1
1mol 2-bromine furans, the methyl iodide of 1mol, pungent-2, the 5-diene of two rings [2.2.2] of 0.1mol, the Pd (OAc) of 10mmol is added in 1L single port flask
2, 1mol alcohol compound R
2oH (anhydrous methanol), the salt of wormwood of 1mol, the anhydrous methanol of 80mL, then the CO gas of 1 normal atmosphere (i.e. 0.1MPa) is filled with, reflux 12 hours (temperature of back flow reaction is 64 DEG C), be cooled to removal of solvent under reduced pressure after room temperature, then add H
2o (100mL), then add extraction into ethyl acetate (3 × 100mL), merge organic layer, anhydrous sodium sulfate drying, obtains 3-methyl methylfuroate
productive rate 85%.Its physical constant is:
1h NMR (400MHz, CDCl
3) δ 7.20 (d, J=2.5Hz, 1H), 7.03 (d, J=2.5Hz, 1H), 4.12 (s, 3H), 2.15 (s, 3H).
Embodiment 2: the difference of the present embodiment and embodiment 1 is that the methyl iodide in step (1) is iodoethane, and obtained compound is 3-ethyl methylfuroate
the yield of product is 69%, and its physical constant is:
1h NMR (400MHz, CDCl
3) δ 7.23 (d, J=2.6Hz, 1H), 7.06 (d, J=2.6Hz, 1H), 4.15 (s, 3H), 2.13 (m, 3H), 1.02 (t, J=7.2Hz, 3H).
Embodiment 3: the methyl iodide that the difference of the present embodiment and embodiment 1 is in step (1) is that to obtain compound be 3-sec.-propyl methylfuroate to 2-iodopropane
the yield of product is 75%, and its physical constant is:
1h NMR (400MHz, CDCl
3) δ 7.42 (d, J=2.8Hz, 1H), 6.78 (d, J=2.8Hz, 1H), 4.08 (s, 3H), 2.17 (m, 1H), 1.30 (d, J=7.8Hz, 6H).
Embodiment 4: the difference of the present embodiment and embodiment 1 is that the methyl iodide in step (1) is 1-butyl iodide, and obtained compound is 3-butyl methylfuroate
the yield of product is 84%, and its physical constant is:
1h NMR (400MHz, CDCl
3) δ 7.62 (d, J=2.8Hz, 1H), 6.85 (d, J=2.8Hz, 1H), 4.04 (s, 3H), 2.24 (t, J=7.2Hz, 3H), 1.54 (m, 2H), 1.27 (m, 2H), 0.95 (t, J=6.6Hz, 3H).
Embodiment 5: the difference of the present embodiment and embodiment 1 is that the methyl alcohol in step (1) is ethanol, and obtained compound is 3-methyl ethyl furoate
the yield of product is 80%, and its physical constant is:
1h NMR (400MHz, CDCl
3) δ 7.66 (d, J=2.5Hz, 1H), 6.74 (d, J=2.5Hz, 1H), 4.25 (q, J=7.2Hz, 2H), 1.35 (s, J=7.2Hz, 3H).
Embodiment 6: the difference of the present embodiment and embodiment 1 is that the methyl alcohol in step (1) is 1-propyl alcohol, and obtained compound is 3-methyl furancarboxylic acid propyl ester
the yield of product is 79%, and its physical constant is:
1h NMR (400MHz, CDCl
3) δ 7.59 (d, J=2.8Hz, 1H), 6.98 (d, J=2.8Hz, 1H), 4.18 (t, J=6.6Hz, 2H), 2.15 (s, 3H), 1.32 (m, 2H), 0.95 (t, J=7.6Hz, 3H).
Embodiment 7: the difference of the present embodiment and embodiment 1 is that the methyl alcohol in step (1) is n-butyl alcohol, and obtained compound is 3-methyl butyl pyromucate
the yield of product is 87%, and its physical constant is:
1h NMR (400MHz, CDCl
3) δ 7.64 (d, J=2.6Hz, 1H), 6.89 (d, J=2.6Hz, 1H), 4.15 (t, J=6.6Hz, 2H), 2.15 (s, 3H), 1.74 (m, 2H), 1.29 (m, 2H), 0.87 (t, J=7.6Hz, 3H).
Embodiment 8: add 1mol 2-iodofuran, the iodopropane of 100mol, (two rings [2.1.1] hept-2-ene") of 0.1mol in 1L single port flask
pd (the PPh of 10mmol
3)
4, 1mol alcohol compound R
2the salt of wormwood of OH (anhydrous methanol), 1mol, the organic solvent (anhydrous methanol) of 80mL, is then filled with 10 atmospheric CO gases, reflux 1 hour (temperature of back flow reaction is 140 DEG C), be cooled to removal of solvent under reduced pressure after room temperature, then add H
2o (100mL), extraction into ethyl acetate (3 × 100mL), merges organic layer, anhydrous sodium sulfate drying.Removed under reduced pressure solvent, the underpressure distillation of gained head product obtains 3-methyl methylfuroate
productive rate 82%.Its physical constant is identical with embodiment 1.
Embodiment 9: the difference of the present embodiment and embodiment 8 is in step (1)
become the own-2-alkene of two rings [2.1.1], obtained compound is 3-methyl methylfuroate
the yield of product is 80%.Its physical constant is identical with embodiment 1.
Embodiment 10: the difference of the present embodiment and embodiment 8 is in step (1)
become two rings [2.1.1] oct-2-ene, obtained compound is 3-methyl methylfuroate
the yield of product is 75%.Its physical constant is identical with embodiment 1.
Embodiment 11: the difference of the present embodiment and embodiment 8 is in step (1)
become diene in two rings [2.2.1] heptan-2,5-, obtained compound is 3-methyl methylfuroate
the yield of product is 65%.Its physical constant is identical with embodiment 1.
Embodiment 12: the difference of the present embodiment and embodiment 8 is in step (1)
become two rings [3.2.1]-6-in ninth of the ten Heavenly Stems alkene, obtained compound is 3-methyl methylfuroate
the yield of product is 89%.Its physical constant is identical with embodiment 1.
Embodiment 13: add 1mol 2-bromine furans, the methyl iodide of 1mol, pungent-2, the 5-diene of two rings [2.2.2] of 0.1mol, the Pd (OAc) of 10mmol in 1L single port flask
2, 1mol alcohol compound R
2oH (anhydrous methanol), the organic solvent (anhydrous methanol) of cesium carbonate (1mol), 80mL, is then filled with the CO gas of 0.1MPa, reflux 12 hours (temperature of back flow reaction is 64 DEG C), be cooled to removal of solvent under reduced pressure after room temperature, then add H
2o (100mL), and then add extraction into ethyl acetate (3 × 100mL), merge organic layer, anhydrous sodium sulfate drying.Removed under reduced pressure solvent, the 3-methyl methylfuroate of gained head product underpressure distillation
productive rate 75%.Its physical constant is identical with embodiment 1.
Embodiment 14: the difference of the present embodiment and embodiment 13 is that the cesium carbonate in step (1) changes potassiumphosphate into, and gained head product is 3-methyl methylfuroate
productive rate 70%.Its physical constant is identical with embodiment 1.
Embodiment 15: the difference of the present embodiment and embodiment 13 is that the cesium carbonate in step (1) changes potassium acetate into, and gained head product is 3-methyl methylfuroate
productive rate 71%.Its physical constant is identical with embodiment 1.
Embodiment 16: the difference of the present embodiment and embodiment 13 is that the cesium carbonate in step (1) changes sodium carbonate into, and gained head product is 3-methyl methylfuroate
productive rate 84%.Its physical constant is identical with embodiment 1.
Embodiment 17: the difference of the present embodiment and embodiment 13 is that the cesium carbonate in step (1) changes potassium hydroxide into, and gained head product is 3-methyl methylfuroate
productive rate 84%.Its physical constant is identical with embodiment 1.
Embodiment 18: add 1mol 2-bromine furans, the methyl iodide of 1mol, pungent-2, the 5-diene of two rings [2.2.2] of 0.1mol, the Pd (CH of 10mmol in 1L single port flask
3cN)
2cl
2, 1mol alcohol compound R
2oH (anhydrous methanol), the organic solvent (anhydrous methanol) of salt of wormwood (1mol), 80mL, is then filled with the CO gas of 0.5MPa, reflux 12 hours (temperature of back flow reaction is 64 DEG C), be cooled to removal of solvent under reduced pressure after room temperature, then add H
2o (100mL), and then add extraction into ethyl acetate (3 × 100mL), merge organic layer, anhydrous sodium sulfate drying.Removed under reduced pressure solvent, gained head product is 3-methyl methylfuroate
productive rate 81%.Its physical constant is identical with embodiment 1.
Embodiment 19: the difference of the present embodiment and embodiment 18 is the Pd (CH in step (1)
3cN)
2cl
2change tetra-triphenylphosphine palladium into, gained head product is 3-methyl methylfuroate
productive rate 90%.Its physical constant is identical with embodiment 1.
Embodiment 20: the difference of the present embodiment and embodiment 18 is the Pd (CH in step (1)
3cN)
2cl
2change Palladous chloride into, gained head product is 3-methyl methylfuroate
productive rate 92%.Its physical constant is identical with embodiment 1.
Embodiment 21: the difference of the present embodiment and embodiment 18 is the Pd (CH in step (1)
3cN)
2cl
2change Pd into
2(dba)
3, gained head product is 3-methyl methylfuroate
productive rate 87%.Its physical constant is identical with embodiment 1.
Embodiment 22: add 1mol 2-bromine furans, the methyl iodide of 1mol, pungent-2, the 5-diene of two rings [2.2.2] of 0.1mol, the Pd (CH of 10mmol in 1L single port flask
3cN)
2cl
2, 1mol alcohol compound R
2oH (anhydrous methanol), the tetrahydrofuran (THF) of salt of wormwood (1mol), 80mL, is then filled with the CO gas of 0.1MPa, reflux 12 hours (temperature of back flow reaction is 64 DEG C), is cooled to removal of solvent under reduced pressure after room temperature, then adds H
2o (100mL), and then add extraction into ethyl acetate (3 × 100mL), merge organic layer, anhydrous sodium sulfate drying.Removed under reduced pressure solvent, gained head product is
productive rate 79%.Its physical constant is identical with embodiment 1.
Embodiment 23: the difference of the present embodiment and embodiment 22 is that the tetrahydrofuran (THF) in step (1) changes toluene into, and gained head product is
productive rate 75%.Its physical constant is identical with embodiment 1.
Embodiment 24: the difference of the present embodiment and embodiment 22 is that the tetrahydrofuran (THF) in step (1) changes Isosorbide-5-Nitrae-dioxane into, and gained head product is
productive rate 64%.Its physical constant is identical with embodiment 1.
Embodiment 25: the difference of the present embodiment and embodiment 22 is that the tetrahydrofuran (THF) in step (1) changes dimethyl sulfoxide (DMSO) (DMSO) into, and gained head product is
productive rate 70%.Its physical constant is identical with embodiment 1.
The above embodiment of the present invention is only for example of the present invention is clearly described, and is not the restriction to embodiments of the present invention.For those of ordinary skill in the field, can also make other changes in different forms on the basis of the above description.Here exhaustive without the need to also giving all embodiments.All any amendments done within the spirit and principles in the present invention, equivalent to replace and improvement etc., within the protection domain that all should be included in the claims in the present invention.
Claims (10)
1. the preparation method of a 3-alkyl Pityrosporum follicuitis, it is characterized in that: specifically comprise the following steps: halo-furan, halohydrocarbon, part, transition-metal catalyst, alcohol compound and alkali are added in organic solvent, be filled with CO gas, back flow reaction 1-60 hour at 0 DEG C ~ 140 DEG C temperature, aftertreatment obtains 3-alkyl Pityrosporum follicuitis;
The structural formula of described halo-furan is
wherein X is haloid element;
Described part is the own-2-alkene of two rings [2.1.1], two rings [2.1.1] hept-2-ene", two rings [2.1.1] oct-2-ene, two rings [2.2.1] heptan-2,5-diene, more than one in pungent-2, the 5-diene of two rings [2.2.2] or two rings [3.2.1]-6-in ninth of the ten Heavenly Stems alkene.
2. the preparation method of 3-alkyl Pityrosporum follicuitis according to claim 1, is characterized in that: described halo-furan be in 2-bromine furans or 2-iodofuran more than one.
3. the preparation method of 3-alkyl Pityrosporum follicuitis according to claim 1, is characterized in that: the structural formula of described halohydrocarbon is: R
1y, wherein Y=Cl, Br, I; R
1for C
1-6aliphatic saturated hydrocarbon or C
2-6unsaturated alkyl.
4. the preparation method of 3-alkyl Pityrosporum follicuitis according to claim 1, is characterized in that: described alcohol compound structural formula is R
2oH, R
2for C
1-6aliphatic saturated hydrocarbon or C
2-8unsaturated alkyl.
5. the preparation method of 3-alkyl Pityrosporum follicuitis according to claim 1, is characterized in that: the structural formula of described 3-alkyl Pityrosporum follicuitis is as follows:
R
1for C
1-6aliphatic saturated hydrocarbon or C
2-6unsaturated alkyl; R
2for C
1-6aliphatic saturated hydrocarbon or C
2-8unsaturated alkyl.
6. the preparation method of 3-alkyl Pityrosporum follicuitis according to claim 1 or 5, is characterized in that: described 3-alkyl Pityrosporum follicuitis is:
7. the preparation method of 3-alkyl Pityrosporum follicuitis according to claim 1 or 5, is characterized in that: described 3-alkyl Pityrosporum follicuitis is:
8. the preparation method of 3-alkyl Pityrosporum follicuitis according to claim 1, is characterized in that:
Described organic solvent is methyl alcohol, ethanol, Virahol, the trimethyl carbinol, methylene dichloride, chloroform, 1,2-ethylene dichloride, toluene, dimethylbenzene, tetrahydrofuran (THF), 1,4-dioxane, more than one in glycol dimethyl ether, dimethyl formamide or dimethyl sulfoxide (DMSO);
Described transition-metal catalyst is Pd (OAc)
2, PdCl
2, PdBr
2, Pd (CH
3cN)
2cl
2, Pd (PPh
3)
4or Pd
2(dba)
3in more than one;
Described alkali is more than one in triethylamine, imidazoles, pyridine, DMAP, salt of wormwood, sodium carbonate, cesium carbonate, potassiumphosphate, sodium sulfate, saleratus, sodium hydroxide, potassium hydroxide, cesium hydroxide, sodium hydride, sodium tert-butoxide, potassium tert.-butoxide or trimethyl carbinol lithium.
9. the preparation method of 3-alkyl Pityrosporum follicuitis according to claim 1, is characterized in that:
The mol ratio of described halo-furan and halohydrocarbon is (100:1) ~ (1:100); The mol ratio of described halo-furan and alcohol compound is (100:1) ~ (1:100); The mol ratio of described halo-furan and transition-metal catalyst is (100:1) ~ (1:100);
The mol ratio of described halo-furan and part is (100:1) ~ (1:100), and the mol ratio of described halo-furan and alkali is (100:1) ~ (1:100);
Described halohydrocarbon is 1mol:(50-80 with the molecular volume ratio of organic solvent) mL.
10. the preparation method of 3-alkyl Pityrosporum follicuitis according to claim 1, is characterized in that: described in be filled with CO normal atmosphere be 1-10 standard atmospheric pressure.
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