CN106632217A - (4S, 7RS)-galaxolide synthesis method - Google Patents
(4S, 7RS)-galaxolide synthesis method Download PDFInfo
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- C07D311/94—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
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Abstract
The invention belongs to the technical field of chemical synthesis of essences and flavors and particularly relates to a (4S, 7RS)-galaxolide synthesis method. The method includes: subjecting bromo-pentamethyl indane and metallic magnesium to reaction to generate a Grignard reagent, and then subjecting to reaction with tetramethoxyl silane to obtain pentamethyl indane silane; subjecting the pentamethyl indane silane to asymmetric Hiyama cross coupling reaction with racemic 2-bromopropionate under catalysis of (1S, 2S)-N,N-dimethyl-1,2-diphenyl diaminoethane and nickel chloride to synthesize (S)-hexamethyl indane acid ester; reducing the (S)-hexamethyl indane acid ester by diisobutyl aluminum hydride (DIBAL-H) to obtain (S)-hexamethyl indanol, and finally subjecting to reaction with paraformaldehyde to obtain (4S, 7RS)-galaxolide. The (4S, 7RS)-galaxolide synthesis method is simple in synthetic route and mild in reaction condition, the overall yield reaches 40%, and product optical purity is 91%.
Description
Technical field
The invention belongs to spices and essence chemosynthesis technical field, and in particular to a kind of new synthesis (4S, 7RS)-Jia Le
The method of Moschus.
Background technology
Jiale muskiness (Galaxolide) is a kind of polycyclic class synthetic musk, by International Flavors & Fragrances Inc. of the U.S.
(IFF) scientist Heeringa and Beets synthesizes first (Heeringa, L.G.;Beets,M.G.J.Patent
US3360530,1967,12,26).Jiale muskiness is with giving off a strong fragrance, and odor type is graceful, and lasting is lasting, good stability, nontoxic etc.
Plurality of advantages, be widely used in cosmetics, tobacco essence, flavoring essence etc. (Tang Jian, contemporary chemical industry, 2008,37,218-
220.Correia,P.;Cruz,A.;Santos,L.;Alves,A.Int.J.Cosmet.Sci.2013,35,299–309.).
The research of Frater shows that (4S, 7R)-Jiale muskiness has strong muskiness with (4S, 7S)-Jiale muskiness, and its is non-
Enantiomter (4R, 7R)-Jiale muskiness and (4R, 7S)-Jiale muskiness almost tasteless (Frater, G.;Muller,U.;
Kraft,P.Helv.Chim.Acta 1999,82(10),1656-1665.).The structural formula of (4S, 7RS)-Jiale muskiness such as formula 1
It is shown, its structure above all chirality methyl of 4.
Jiale muskiness (Galaxolide) is a kind of maximum synthetic musk of current usage amount, thus, in soil, water
Jiale muskiness (Heberer, T.Acta Hydrochim.Hydrobio.2003,30,227- is can detect that in body and air
243.;Weschler,C.J.;Nazaroff,W.W.Indoor Air 2012,22,356-377.).The residual of Jiale muskiness is asked
Topic is gradually taken seriously, and needs to reduce its pollution to environment.Thus, aromatic (4S, the 7RS)-Jiale muskiness of research synthesis tool
With important using value.At present, synthesize (4S, 7RS)-Jiale muskiness method only have two kinds, i.e. chiral source method with it is not right
Claim catalysis method.
(1) chiral source method is reacted with pentamethyl indane using the optically pure expoxy propane of chiral raw material, generates hexamethyl
Indanol, then reacts again with formaldehyde and generates object (4S, 7RS)-Jiale muskiness (Frater, G.;Mueller,U.;
Petrzilka,M.PatentEP0677521A,1995,2,22.)。
(2) asymmetry catalysis method be with pentamethyl indane as initiation material, Jing bromos, be coupled and hydroformylation reaction,
Then using the asymmetric hydrogenation of alkene, the acid of (S)-hexamethyl indane is obtained, then Jing reduction generates (S)-hexamethyl indane
Alcohol, finally obtains (4S, 7RS)-Jiale muskiness (Ciappa, A. with polyformaldehyde reaction;Matteoli,U.;Scrivanti,
A.Tetrahedron:Asymmetry 2002,13,2193-2195.)。
Although there is needs in the existing several reports of research with regard to synthesizing (4S, 7RS)-Jiale muskiness, existing method
Learn the chiral source reagent of dosage, the problems such as synthetic route is loaded down with trivial details.Therefore, study new, efficient, environment amenable, simple and direct
Synthesis (4S, 7RS)-Jiale muskiness method, have great importance.
The content of the invention
For these reasons, applicant obtains a kind of new synthesis (4S, 7RS)-Jia Le musk deers through creative research for many years
Fragrant method, the method is adopted:Bromo pentamethyl indane generates RMgBr with magnesium metal, then reacts with tetramethoxy-silicane
Obtain pentamethyl indane silane;Pentamethyl indane silane is again in (1S, 2S)-N, N- dimethyl -1,2- diphenyl ethylene diamines and chlorine
Under changing the catalysis of nickel, there is asymmetric Hiyama cross-coupling reactions with racemic 2- ester bromopropionylaminos and synthesize (S)-hexamethyl
Indane acid esters;(S)-hexamethyl indane acid esters Jing diisobutyl aluminium hydrides (DIBAL-H) is reduced to (S)-hexamethyl indanol, most
Obtain (4S, 7RS)-Jiale muskiness with polyformaldehyde reaction afterwards.Synthetic route of the present invention is simple and direct, and reaction condition is gentle, gross production rate
For 40%, product optical purity is 91%.
The present invention is intended to provide a kind of asymmetric Hiyama cross-coupling reactions synthesis (4S, 7RS)-Jia Le musk deers of nickel catalysis
Fragrant new method.The present invention generates grignard examination with bromo pentamethyl indane (being labeled as 1 in formula 2) as initiation material with magnesium metal
Agent (is labeled as 2) in formula 2, then obtains pentamethyl indane silane (being labeled as 3 in formula 2) with tetramethoxy-silicane reaction.Exist again
Under the catalysis of (1S, 2S)-N, N- dimethyl -1,2- diphenyl ethylene diamines and nickel chloride, send out with racemic 2- ester bromopropionylaminos
The asymmetric Hiyama cross-coupling reactions of life, in the alpha-position of ester group pentamethyl indane is introduced, and synthesizes (S)-hexamethyl indane acid esters
(being labeled as 4 in formula 2), Jing diisobutyl aluminium hydrides (DIBAL-H) are reduced to (S)-hexamethyl indanol (being labeled as 5 in formula 2).
(4S, 7RS)-Jiale muskiness is finally obtained with polyformaldehyde reaction.The concrete route of present invention synthesis (4S, 7RS)-Jiale muskiness
Referring to formula 2.
What the present invention was achieved through the following technical solutions.
A kind of synthetic method of (4S, 7RS)-Jiale muskiness, comprises the steps:Bromo pentamethyl indane is given birth to magnesium metal
Into RMgBr, then pentamethyl indane silane is obtained with tetramethoxy-silicane reaction;Pentamethyl indane silane again (1S,
Under the catalysis of 2S)-N, N- dimethyl -1,2- diphenyl ethylene diamines and nickel chloride, occur not with racemic 2- ester bromopropionylaminos
Symmetrical Hiyama cross-coupling reactions synthesis (S)-hexamethyl indane acid esters;(S)-hexamethyl indane acid esters Jing diisobutyls hydrogenation
Aluminium (DIBAL-H) is reduced to (S)-hexamethyl indanol, and (4S, 7RS)-Jiale muskiness is finally obtained with polyformaldehyde reaction.
The synthetic method of wherein pentamethyl indane silane is:Under argon gas protection, bromo pentamethyl indane generates lattice with magnesium powder
Family name's reagent, in instilling the tetrahydrofuran solution of tetramethoxy-silicane, the stirring reaction at -30 DEG C is warming up to room temperature, continues to stir
Organic solvent diluting reactant liquor is used in reaction, reaction after terminating, Jing washings, dry, reduced pressure concentration are finally pure with silica gel column chromatography
Change, pentamethyl indane silane is obtained.
The synthetic method of wherein (S)-hexamethyl indane acid esters is:Under argon gas protection, by racemic 2- halopropanoic acids ester
NiCl and (1S, 2S)-N are sequentially added with pentamethyl indane silane, N- dimethyl -1, in the solution of 2- diphenyl ethylene diamines, room
Warm lower stirring reaction, reaction is quenched reaction after terminating, Jing point of liquid, extraction, NaCl solution washing, dry, reduced pressure concentration are finally used
Silica gel chromatography, is obtained (S)-hexamethyl indane acid esters.
The synthetic method of wherein (S)-hexamethyl indanol is:Under argon gas protection, at -78 DEG C, by diisobutyl aluminium hydride
(DIBAL-H) toluene solution is instilled in the dichloromethane solution of (S)-hexamethyl indane acid esters, stirring reaction, and reactant liquor heats up
To 0 DEG C, continue stirring reaction, reaction is quenched reaction after terminating, and adds aqueous sodium potassium tartrate, stirs under room temperature, Jing divide liquid,
Extraction, dry, reduced pressure concentration, finally with silica gel chromatography, are obtained (S)-hexamethyl indanol.
The synthetic method of wherein (4S, 7RS)-Jiale muskiness is:In the dichloromethane solution of (S)-hexamethyl indanol,
Phosphorus pentachloride and paraformaldehyde are sequentially added, at 50 DEG C, adds suitable quantity of water, stirring reaction to react after terminating, recycling design,
Divide liquid, alkali cleaning, be heated to reflux;Ethyl acetate dissolving is added, the washing of Jing NaCl solutions, dry, reduced pressure concentration finally use silicagel column
Chromatogram purification, is obtained (4S, 7RS)-Jiale muskiness.
Specific embodiment
Embodiment 1
The synthesis of pentamethyl indane silane
Under argon gas protection, magnesium powder (0.23g, 9mmol) is added in 20mL Schlenk reaction bulbs, be vacuum dried 2h.Plus
Enter the tetrahydrofuran solution 2mL of bromo pentamethyl indane (0.54g, 2mmol), mixture is slowly heated into initiation instead at 50 DEG C
Should, it is then slowly added into the tetrahydrofuran solution 4mL of remaining bromo pentamethyl indane (1.07g, 4mmol).Add bromo-derivative
Afterwards, reactant mixture is carefully heated to backflow, continues heating stirring reaction 5h, pentamethyl indane RMgBr is obtained.
Under argon gas protection, tetramethoxy-silicane (2.74g, 18mmol) and tetrahydrochysene are added in 50mL Schlenk reaction bulbs
Furans (10mL), stirs.Mixeding liquid temperature is down into -30 DEG C, the four of pentamethyl indane RMgBr are then added dropwise over
Hydrogen tetrahydrofuran solution 6mL.Stirring reaction 1h at -30 DEG C, is then to slowly warm up to room temperature, continues stirring reaction 12h.Reaction terminates
Afterwards, reaction mixture is diluted with 60mL pentanes.Deionized water (3 × 30mL) is washed, and Jing anhydrous magnesium sulfates are dried, decompression
It is concentrated to give crude product.Finally use silica gel column chromatography (petrol ether/ethyl acetate 30:1) purify, grease pentamethyl indane silicon is obtained
Alkane (1.30g, yield 70%).1H NMR(400MHz,CDCl3)δ7.28-7.03(m,3H),3.59(s,9H),1,90(q,1H),
1.30(s,6H),1.10(s,6H),1.03(d,3H).HRMS(APCI-TOF)calcd for C17H28O3Si[M]+
308.1808,found308.1796.
Embodiment 2
(S) synthesis of-hexamethyl indane acid esters
Under argon gas protection, in 50mL Schlenk reaction bulbs NiCl is added2.glyme (22.0mg, 0.1mmol),
[F2SiPh3]-[NBu4]+(TBAT, 1080mg, 2.0mmol) and (1S, 2S)-N, N- dimethyl -1,2- diphenyl ethylene diamines
(28.8mg, 0.12mmol), is subsequently adding dioxane (20mL).10min is stirred the mixture for, pentamethyl indane silane is added
(401mg, 1.3mmol) and 2- bromo acids -2,6- di-t-butyls -4- toluene esters (355.3mg, 1mmol).By reactant mixture
Continue stirring reaction 18h at room temperature.Add the mixed solution (1 of 1M hydrochloric acid and acetone:1,10mL), 2h is stirred.By mixture
Pour water (50mL) into, separate organic phase.Water is mutually extracted with ether (3 × 50mL).Merge organic phase, use saturation NaCl solution
(50mL) wash.The anhydrous MgSO of Jing4It is dried, reduced pressure concentration obtains crude product.Finally use silica gel column chromatography (petrol ether/ethyl acetate
60:1) purify, oily liquids (S)-hexamethyl indane acid esters (370.2mg, yield 80%, optical purity 91%) is obtained.[α]D 20
=+7.5 (c 1.3, CHCl3).1H NMR(400MHz,CDCl3)δ7.23-7.05(m,5H),3.76(q,1H),2.33(s,
3H),1.88(q,1H),1.65(d,3H),1.38(s,9H),1.28(s,6H),1.08(s,6H),1.01(d,3H),0.94(s,
9H).HRMS(APCI-TOF)calcd for C32H47O2[M+H]+463.3576,found 463.3566.
Embodiment 3
(S) synthesis of-hexamethyl indanol
Under argon gas protection, in 20mL Schlenk reaction bulbs anhydrous CH is added2Cl2(10mL), (S)-hexamethyl indenes is added
Full acid esters (1.85g, 5mmol), stirs.Mixeding liquid temperature is down into -78 DEG C, diisobutyl aluminium hydride is slowly added to
(DIBAL-H) (7.5mL, 1.5M toluene solution, 11mmol).After completion of dropping, stirring reaction 30min is continued at -78 DEG C, so
Afterwards reaction mixture temperature is risen into 0 DEG C, be stirred for reacting 30min.After reaction terminates, reaction mixture temperature is down into -78
DEG C, reaction is quenched with methyl alcohol (1mL).Aqueous sodium potassium tartrate (22mL, 0.5M, 11mmol) is added, by the mixed liquor of gained
Temperature is slowly increased to room temperature, continues to stir 12h.Organic phase is separated, water mutually uses CH2Cl2(3 × 20mL) is extracted.Merge organic phase,
Use anhydrous Na2SO4It is dried, reduced pressure concentration.Finally use silica gel chromatography (petrol ether/ethyl acetate 8:1), obtain colourless solid
Body (S)-hexamethyl indanol (1.11g, yield 90%, optical purity 91%).[α]D 20=-6.8 (c 1.1, EtOH).1H
NMR(400MHz,CDCl3)δ7.26-7.02(m,3H),3.73-3.65(m,2H),3.00-2.88(m,1H),1.87(q,1H),
1.40(br t,1H),1.30(d,3H),1.27(s,6H),1.09(s,6H),1.00(d,3H).HRMS(APCI-TOF)calcd
for C17H15[M-OH]+229.1956,found 229.1962.
Embodiment 4
The synthesis of (4S, 7RS)-Jiale muskiness
(S)-hexamethyl indanol (2.46g, 10mmol) and dichloromethane (10mL), room temperature are added in 50mL reaction bulbs
Lower stirring and dissolving.Then phosphorus pentachloride (2.08g, 10mmol) is dividedly in some parts, after stirring 10min, paraformaldehyde is carefully added into
(0.6g, 20mmol), stirs 10min.Reacting liquid temperature is slowly increased into 50 DEG C, 3mL water is slowly added dropwise, continues stirring reaction
6h.After reaction terminates, 3mL water, Distillation recovery dichloromethane, residual solution stratification are added.Organic phase is separated, organic phase is used
The 10%NaOH aqueous solution (10mL) is washed.Organic phase after alkali cleaning is heated to reflux 1h, adds ethyl acetate (10mL) dissolving, uses full
With the NaCl aqueous solution (10mL) washing.Jing anhydrous Nas2SO4It is dried, reduced pressure concentration obtains crude product.Jing silica gel column chromatographies (oil after most
Ether/ethyl acetate 95:5) purify, obtain colorless solid (4S, 7RS)-Jiale muskiness (2.06g, yield 80%, optical purity
91%).[α]D 20=-17.5 (c 1.2, CHCl3).1H NMR(400MHz,CDCl3)δ7.03(s,1H),6.78(s,1H),
4.83(d,1H),4.75(d,1H),3.96(dd,1H),3.67(dd,1H),2.97-2.85(m,1H),1.86(q,1H),1.33
(d,3H),1.28(s,6H),1.09(s,6H),1.01(d,3H).HRMS(APCI-TOF)calcd for C18H26O[M]+
258.1984,found258.1992.
Although being described to embodiment of the present invention above, above-mentioned being embodied as is the invention is not limited in
Scheme and application, above-mentioned specific embodiment is only schematic, guiding rather than restricted.Ability
The those of ordinary skill in domain is under the enlightenment of this specification and in the situation of the scope protected without departing from the claims in the present invention
Under, the form of many kinds can also be made, these belong to the row of protection of the invention.
Claims (5)
1. a kind of synthetic method of (4S, 7RS)-Jiale muskiness, it is characterised in that comprise the steps:Bromo pentamethyl indane with
Magnesium metal generates RMgBr, then obtains pentamethyl indane silane with tetramethoxy-silicane reaction;Pentamethyl indane silane is again
Under the catalysis of (1S, 2S)-N, N- dimethyl -1,2- diphenyl ethylene diamines and nickel chloride, with racemic 2- ester bromopropionylaminos
The asymmetric Hiyama cross-coupling reactions of generation synthesize (S)-hexamethyl indane acid esters;(S)-isobutyls of hexamethyl indane acid esters Jing bis-
Base aluminum hydride (DIBAL-H) is reduced to (S)-hexamethyl indanol, and (4S, 7RS)-Jia Le musk deers are finally obtained with polyformaldehyde reaction
It is fragrant.
2. it is according to claim 1 one kind (4S, 7RS)-Jiale muskiness synthetic method, it is characterised in that synthesis pentamethyl
The method of indane silane is:Under argon gas protection, bromo pentamethyl indane generates RMgBr with magnesium powder, instills tetramethoxy-silicane
Tetrahydrofuran solution in, the stirring reaction at -30 DEG C is warming up to room temperature, continues stirring reaction, reaction terminate after with organic molten
Dilution agent reactant liquor, Jing washings, dry, reduced pressure concentration, finally with silica gel chromatography, are obtained pentamethyl indane silane.
3. it is according to claim 1 one kind (4S, 7RS)-Jiale muskiness synthetic method, it is characterised in that synthesis (S)-six
The method of methyl indan acid esters is:Under argon gas protection, racemic 2- halopropanoic acids ester is added successively with pentamethyl indane silane
Enter NiCl and (1S, 2S)-N, N- dimethyl -1, in the solution of 2- diphenyl ethylene diamines, stirring reaction under room temperature, after reaction terminates
Reaction is quenched, Jing point of liquid, extraction, NaCl solution washing, dry, reduced pressure concentration, finally with silica gel chromatography, are obtained
((S)-hexamethyl indane acid esters.
4. it is according to claim 1 one kind (4S, 7RS)-Jiale muskiness synthetic method, it is characterised in that synthesis (S)-six
The method of methyl indan alcohol is:Under argon gas protection, at -78 DEG C, the toluene solution of diisobutyl aluminium hydride (DIBAL-H) is instilled
(S) in the dichloromethane solution of-hexamethyl indane acid esters, stirring reaction, reactant liquor is warming up to 0 DEG C, continues stirring reaction, reaction
Reaction is quenched after end, aqueous sodium potassium tartrate is added, is stirred under room temperature, Jing point of liquid, extraction, drying, reduced pressure concentration, finally
With silica gel chromatography, (S)-hexamethyl indanol is obtained.
5. it is according to claim 1 one kind (4S, 7RS)-Jiale muskiness synthetic method, it is characterised in that synthesis (4S,
The method of 7RS)-Jiale muskiness is:In the dichloromethane solution of (S)-hexamethyl indanol, sequentially add phosphorus pentachloride with it is many
Polyformaldehyde, at 50 DEG C, adds suitable quantity of water, stirring reaction to react after terminating, and recycling design, point liquid, alkali cleaning are heated to reflux;Plus
Enter ethyl acetate dissolving, Jing NaCl solutions are washed, are dried, reduced pressure concentration, finally with silica gel chromatography, be obtained (4S,
7RS)-Jiale muskiness.
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111170829A (en) * | 2020-02-28 | 2020-05-19 | 万华化学集团股份有限公司 | Preparation method of hexamethyl indanol |
CN112321557A (en) * | 2020-09-14 | 2021-02-05 | 万华化学集团股份有限公司 | Preparation method of Jiale musk |
CN113185487A (en) * | 2021-04-28 | 2021-07-30 | 安徽金轩科技有限公司 | Production process of Jiale musk |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105198722A (en) * | 2015-09-24 | 2015-12-30 | 中国农业大学 | Method for asymmetrically catalyzing and synthesizing (R)-4, 7-dimethyl-1-tetralone |
-
2016
- 2016-11-16 CN CN201611008971.6A patent/CN106632217A/en active Pending
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105198722A (en) * | 2015-09-24 | 2015-12-30 | 中国农业大学 | Method for asymmetrically catalyzing and synthesizing (R)-4, 7-dimethyl-1-tetralone |
Non-Patent Citations (5)
Title |
---|
A. CIAPPA ET AL.: "Asymmetric catalysis in fragrance chemistry: a new synthesis of Galaxolide", 《TETRAHEDRON: ASYMMETRY》 * |
DANIELA SUSTAC ROMAN: "《Encyclopedia of Reagents for Organic Synthesis》", 14 September 2012 * |
P. TANG, T. RITTER: "Silver-mediated fluorination of aryl silanes", 《TETRAHEDRON》 * |
王建新: "《精细有机合成》", 30 April 2007 * |
谭世语等: "佳乐麝香合成工艺的改进", 《化工进展》 * |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111170829A (en) * | 2020-02-28 | 2020-05-19 | 万华化学集团股份有限公司 | Preparation method of hexamethyl indanol |
CN111170829B (en) * | 2020-02-28 | 2022-11-08 | 万华化学集团股份有限公司 | Preparation method of hexamethyl indanol |
CN112321557A (en) * | 2020-09-14 | 2021-02-05 | 万华化学集团股份有限公司 | Preparation method of Jiale musk |
CN112321557B (en) * | 2020-09-14 | 2023-01-13 | 万华化学集团股份有限公司 | Preparation method of Jiale musk |
CN113185487A (en) * | 2021-04-28 | 2021-07-30 | 安徽金轩科技有限公司 | Production process of Jiale musk |
CN113185487B (en) * | 2021-04-28 | 2022-09-23 | 安徽金轩科技有限公司 | Production process of Jiale musk |
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Application publication date: 20170510 |