CN105968009B - 5 isopropyl, 9 hydroxyl, 8 methyl, 6 nonene, 2 ketone oxalic acid dibasic acid esters and its synthetic method and application - Google Patents
5 isopropyl, 9 hydroxyl, 8 methyl, 6 nonene, 2 ketone oxalic acid dibasic acid esters and its synthetic method and application Download PDFInfo
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- CN105968009B CN105968009B CN201610571947.7A CN201610571947A CN105968009B CN 105968009 B CN105968009 B CN 105968009B CN 201610571947 A CN201610571947 A CN 201610571947A CN 105968009 B CN105968009 B CN 105968009B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/14—Preparation of carboxylic acid esters from carboxylic acid halides
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- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
- A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
- A24B15/18—Treatment of tobacco products or tobacco substitutes
- A24B15/28—Treatment of tobacco products or tobacco substitutes by chemical substances
- A24B15/30—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances
- A24B15/32—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances by acyclic compounds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/12—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
- C07D317/20—Free hydroxyl or mercaptan
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- General Chemical & Material Sciences (AREA)
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Abstract
The invention discloses a kind of 6 nonene of 5 isopropyl, 9 hydroxyl, 8 methyl, 2 ketone oxalic acid dibasic acid esters and its synthetic method and application, solanone is dissolved in anhydrous benzene, add ethylene glycol and p-methyl benzenesulfonic acid, solanone condensed ethandiol is obtained after reaction, solanone condensed ethandiol is dissolved in anhydrous THF, monoborane tetrahydrofuran complex, NaOH solution and hydrogen peroxide is added dropwise, reaction obtains 5 isopropyl, 9 hydroxyl, 8 methyl, 6 nonene, 2 ketone condensed ethandiol, is dissolved in anhydrous CH2Cl2, triethylamine and oxalyl chloride are added, 3.5h is reacted at room temperature, obtains 5 isopropyl, 9 hydroxyl, 8 methyl, 6 nonene, 2 ketone oxalic acid dibasic acid esters, the effect being applied in perfuming cigarette mainly improves aroma quality and perfume quantity, reduces irritation, pure pleasant impression.
Description
Technical field
The invention belongs to tobacco aromaticss technical field, and more particularly, it relate to 5- isopropyl -9- hydroxyl -8- methyl -6-
Nonene -2- ketone oxalic acid dibasic acid esters, its preparation method, and the application as spices in cigarette.
Background technology
The suction taste of cigarette, happy degree and satisfaction are the results of flavor component, sense organ and tactile complexing action.Therefore,
The flavor component for finding and developing tobacco is the free-revving engine of many tobacco chemistry men, meanwhile, flavor component is also cigarette
The key problem of brand construction.After accession to WTO, with the reduction and concession of tariff and phasing out for nontariff measures, Chinese tobacco will
Stand and directly take part in international competition on more emulative platform, therefore, how to protrude Chinese-style cigarette distinct characteristic, strengthen autonomous
Innovation also just becomes the key of itself competitiveness of the lifting of China's tobacco enterprise, and core therein is exactly to strengthen tobacco perfume (or spice) skill
The research of art, perfume material.
A traditional tobacco aromaticss part is the material contained by tobacco itself, and another part is external natural or synthetic
Additive, its main aroma component based on terpene, aldehyde, ketone, alcohol, the characteristics of these compounds mainly molecular weight compared with
The stronger compound of low, low boiling point, volatility, loses in high temperature working processes serious, causes to release fragrant non-uniform phenomenon, very
Extremely because volatilization loses fragrance during storage, or unstable chemcial property is easily gone bad by oxidation.Research is found, even if fragrant
The volatile matter of essence loss 2%, which also results in odor type change, is greatly affected flavor.
Solanone is the crucial cause aroma compounds in tobacco, is produced by the biochemical degradation of tobacco Chinese and Western cypress trienes material.Eggplant
Ketone can further be degraded in the modulation of tobacco, ageing process, produce the eggplant Pranoprofenum having a major impact jealous to cigarette, drop eggplant
The materials such as diketone.Although solanone must be applied in tobacco flavoring, there are the problem of be also obvious：Solanone itself boils
Point is low, readily volatilized during cigarette preservation to be lost in so as to reduce sucking quality.Therefore, a kind of structure of synthesis how is designed
Rational solanone derivative, makes it to stablize preservation but also discharges solanone by cracking, become in order to which urgently to be resolved hurrily is asked
Topic.
The content of the invention
It is an object of the invention to a kind of 5- isopropyls -9- hydroxyls -8- methyl -6- nonene -2- ketone oxalic acid dibasic acid esters and its system
Preparation Method and the application as spices in cigarette.
To achieve the above object, the present invention uses following technical scheme：
Following represented 5- isopropyl -9- hydroxyl -8- methyl -6- nonene -2- ketone oxalic acid dibasic acid esters, it is its racemic modification, right
Reflect isomers：
。
The synthetic method of the 5- isopropyl -9- hydroxyl -8- methyl -6- nonene -2- ketone oxalic acid dibasic acid esters, step are as follows：
（1）Solanone is dissolved in anhydrous benzene, adds ethylene glycol and p-methyl benzenesulfonic acid, and plus water knockout drum, flow back 5 h, to nothing
Untill moisture goes out；Reactant uses saturation NaHCO successively3Solution, the washing of saturation NaCl solution, anhydrous Na SO4It is dried overnight, filters,
Vacuum distillation obtains solanone condensed ethandiol, and the structural formula of solanone condensed ethandiol is as follows
：
（2）By step（1）Obtained solanone condensed ethandiol is dissolved in anhydrous THF, is placed in 0 DEG C of constant temperature stirring reactive bath technique, nitrogen
Monoborane tetrahydrofuran complex is added dropwise under gas shielded, reacts 1 h at 0 DEG C, reacts 3.5h after being warmed to room temperature, be slowly added to
The NaOH solution of 3mol/L, continues to be slowly added to the hydrogen peroxide that mass fraction is 30%, the reaction was continued at room temperature 10h, obtains
White suspension, adds ethyl acetate, and organic layer is washed with saturation NaCl, anhydrous Na SO4It is dry, solvent, residue mistake is evaporated off
Silica gel column chromatography, petroleum ether：Ethyl acetate elutes, and obtains 5- isopropyl -9- hydroxyl -8- methyl -6- nonene -2- ketone contractings second two
Alcohol, the structural formula of 5- isopropyl -9- hydroxyl -8- methyl -6- nonene -2- ketone condensed ethandiols are as follows
：
（3）By step（2）Obtained 5- isopropyls -9- hydroxyls -8- methyl -6- nonene -2- ketone condensed ethandiols are dissolved in anhydrous
CH2Cl2, triethylamine is added, oxalyl chloride is slow added at 0 DEG C, is warmed to room temperature lower reaction 3.5h, ethyl acetate dilution is added, has
Machine layer is washed with saturation NaCl, anhydrous Na SO4It is dry, solvent is evaporated off, residue crosses silica gel column chromatography, petroleum ether：Ethyl acetate
Elution, obtains 5- isopropyl -9- hydroxyl -8- methyl -6- nonene -2- ketone oxalic acid dibasic acid esters, 5- isopropyl -9- hydroxyl -8- methyl -6-
The structural formula of nonene -2- ketone oxalic acid dibasic acid esters is as follows：
；
Synthetic route is as follows：
。
The step（1）Middle solanone, ethylene glycol, the ratio between the amount of material of p-methyl benzenesulfonic acid three are 1：1.5：0.1.
The step（2）The ratio between amount of material of middle solanone condensed ethandiol and monoborane tetrahydrofuran complex is 1:1.5
, it is necessary to 1 mL of NaOH solution, 1 mL of hydrogen peroxide on the basis of 1 mmol solanone condensed ethandiols.
The step（3）Middle 5- isopropyls -9- hydroxyls -8- methyl -6- nonene -2- ketone condensed ethandiol, triethylamine and oxalyl
The ratio between amount of material of chlorine is 1：1.2：0.5.
5- isopropyl -9- hydroxyl -8- methyl -6- nonene -2- ketone oxalic acid the dibasic acid esters is mixed with after stabilizer or diluent
As application of the spices in cigarette.
Beneficial effects of the present invention：（1）Compound 5- isopropyl -9- hydroxyl -8- methyl -6- nonene -2- ketone oxalic acid dibasic acid esters
Property as a kind of latent Studies of The Aromatic Substances, stablize, and solanone is can release when cigarette is burnt and sucked by property, and it is unstable to improve solanone, Yi Hui
The shortcomings that hair, fragrance is easy to lose.
（2）Compound 5- isopropyl -9- hydroxyl -8- methyl -6- nonene -2- ketone oxalic acid dibasic acid esters can carry in perfuming cigarette
High aroma quality and perfume quantity, reduce irritation, pure pleasant impression.
Embodiment
With reference to specific embodiment, the present invention will be further described.It is to be understood that following embodiments are merely to illustrate this
Not for limiting the scope of the invention, the person skilled in the art in the field can make one according to the content of foregoing invention for invention
A little nonessential modifications and adaptations.
Embodiment 1
The synthetic method of the 5- isopropyl -9- hydroxyl -8- methyl -6- nonene -2- ketone oxalic acid dibasic acid esters of the present embodiment is as follows：
（1）Solanone condensed ethandiol（Ⅱ）Synthesis
Solanone（1.94 g, 10 mmol）It is dissolved in 80 mL anhydrous benzenes, adds ethylene glycol（0.93 g, 0.83 mL, 15
mmol）Water knockout drum is added with p-methyl benzenesulfonic acid (0.2 g, 1 mmol), untill being back to anhydrous separate；Reactant saturation
NaHCO3Solution washs 3 times；Washed 3 times with saturation NaCl solution again, organic phase anhydrous Na SO4Dry, vacuum distillation obtains yellowish
Color oil product（Ⅱ）2.3 g；
MS-EI, m/z 87(100), 93, 121, 136, 176, 223(M+) . 1H NMR (600 MHz,
CDCl3) δ6.07 (d, J = 15.6 Hz, 1H), 5.39 (dd, J = 15.6, 9.5 Hz, 1H), 4.86 (s,
2H), 3.95 -3.90 (m, 5H), 1.83 (s, 3H), 1.81-1.75 (m, 1H), 1.66-1.53 (m, 3H),
1.52-1.45 (m, 1H), 1.37-1.33 (m, 1H), 1.31 (s, 3H), 0.88 (d, J = 6.8 Hz, 4H),
0.84 (d, J = 6.8 Hz, 3H). 13C NMR (151 MHz, CDCl3) δ142.2, 134.2, 132.7,
114.3, 110.3, 64.7, 64.6, 49.7, 37.4, 32.3, 26.8, 23.9, 20.9, 19.5, 18.9.
（2）5- isopropyl -9- hydroxyl -8- methyl -6- nonene -2- ketone condensed ethandiols（Ⅲ）Synthesis
Compound（Ⅱ）(1.28 g, 5.74 mmol) are dissolved in 20 mL anhydrous tetrahydro furans, are placed in cryogenic thermostat stirring
In reactive bath technique, monoborane tetrahydrofuran complex (1 mol/L, 8.6 mL) is added dropwise in 0 DEG C under nitrogen protection, 1 h rises to room
Temperature 3.5 h of reaction, are cooled to 0 DEG C, are slowly added to 5.7 mL 3mol/L NaOH solutions successively, 5.7 mL, 30% hydrogen peroxide,
Finish and be warmed to room temperature 10 h of reaction, add the dilution of 30 mL ethyl acetate, organic layer is washed 3 times with saturation NaCl, anhydrous Na SO4
Dry, vacuum distillation, residue crosses silica gel column chromatography, petrol ether/ethyl acetate=10:1 elution, obtains colorless oil as product
（Ⅲ）690 mg.
MS-ESI, m/z 279 [M+Na]+. 1H NMR (400 MHz, CDCl3) δ5.28 (dd, J = 15.4,
8.7 Hz, 1H), 5.19 (dd, J = 15.4, 7.4 Hz, 1H), 3.95-3.90 (m, 4H), 3.47 (dd, J
= 10.4, 5.7 Hz, 1H), 3.37 (dd, J = 10.4, 7.7 Hz, 1H), 2.37-2.30 (m, 1H),
1.69-1.46 (m, 6H), 1.31 (s, 3H), 1.00 (d, J = 6.8 Hz, 3H), 0.87 (d, J = 6.7
Hz, 3H), 0.83 (d, J = 6.8 Hz, 3H). 13C NMR (100 MHz, CDCl3) δ133.8, 133.7,
110.3, 67.4, 64.6, 49.5, 39.9, 37.3, 31.8, 26.6, 23.7, 20.8, 18.9, 16.8.
（3）5- isopropyl -9- hydroxyl -8- methyl -6- nonene -2- ketone oxalic acid dibasic acid esters（Ⅰ）Synthesis
Compound（Ⅲ）(520 mg, 1.87 mmol) are dissolved in 15 mL anhydrous methylene chlorides, add triethylamine (246
Mg, 2,24 mmol), oxalyl chloride is slowly added dropwise at 0 DEG C（117 mg, 0.93 mmol）, 0.5 h is reacted, it is then anti-at room temperature
3.5 h are answered, add 30 mL ethyl acetate, organic layer is washed 3 times with saturation NaCl, organic to be added to anhydrous Na SO4It is dry, subtract
Solvent is evaporated off in pressure, and residue crosses silica gel column chromatography, petrol ether/ethyl acetate=15:1 elution, obtains colorless oil（Ⅰ）280
mg。
MS-ESI, m/z 501 [M+Na]+. 1H NMR (600 MHz, CDCl3) δ5.24-5.22 (m, 2H),
4.18-4.07 (m, 2H), 2.65-2.60 (m, 1H), 2.42-2.29 (m, 2H), 2.12 (s, 3H), 1.74-
1.67 (m, 2H), 1.56-1.53 (m, 1H), 1.47-1.41 (m, 1H), 1.07 (d, J = 6.8 Hz, 3H),
0.86 (t, J = 6.4 Hz, 3H), 0.81 (t, J = 6.1 Hz, 3H). 13C NMR (150 MHz, CDCl3) δ
209.4, 157.8, 133.3, 132.5, 70.8, 49.0, 41.9, 36.1, 31.9, 30.1, 26.1, 20.7,
19.0, 17.2.
The synthetic route of the present embodiment is as follows：
。
5- isopropyls -9- hydroxyls -8- methyl -6- nonene -2- ketone oxalic acid dibasic acid esters is in perfuming cigarette made from the present embodiment
Application：0.04932 g of 5- isopropyl -9- hydroxyl -8- methyl -6- nonene -2- ketone oxalic acid dibasic acid esters is weighed respectively, with 95% second
Alcohol solution is respectively settled to 10 mL.The solution configured is homogeneously added into Bright Yellow with experiment with essence and flavoring agent injector
In great Jin round roll cigarettes, every cigarette injection volume is 10µL, starts injection point and terminates injection point respectively away from pipe tobacco end 5 mm and 55
Mm, selects and meets cigarette sample claimed below（0.89 g of weight, 1000 Pa of resistance to suction, 24 mm of filter length, cigarette specification 84
mm×2.5 mm）It is evenly placed upon temperature（22±1）DEG C and relative humidity（60±3）48 more than h are balanced in the environment of %, together
Blank sample control is smoked panel test, and the results are shown in Table 1.
1 blank cigarette of table compares smoking result with charging cigarette
Compound 5- isopropyls -9- hydroxyls -8- methyl -6- nonenes -2- ketone oxalic acid dibasic acid esters is in perfuming cigarette as shown in Table 1
Effect mainly improve aroma quality and perfume quantity, reduce irritation, pure pleasant impression.
Claims (6)
1. a kind of 5- isopropyl -9- hydroxyl -8- methyl -6- nonene -2- ketone oxalic acid dibasic acid esters as follows,
。
2. the synthesis side of 5- isopropyls -9- hydroxyls -8- methyl -6- nonene -2- ketone oxalic acid dibasic acid esters according to claim 1
Method, it is characterised in that step is as follows：
（1）Solanone is dissolved in anhydrous benzene, adds ethylene glycol and p-methyl benzenesulfonic acid, and plus water knockout drum, flow back 5 h, to no moisture
Untill going out；Reactant uses saturation NaHCO successively3Solution, the washing of saturation NaCl solution, anhydrous Na SO4It is dried overnight, filters, decompression
Distillation obtains solanone condensed ethandiol, and the structural formula of solanone condensed ethandiol is as follows：
；
（2）By step（1）Obtained solanone condensed ethandiol is dissolved in anhydrous THF, is placed in 0 DEG C of constant temperature stirring reactive bath technique, nitrogen is protected
Shield is lower to be added dropwise monoborane tetrahydrofuran complex, reacts 1 h at 0 DEG C, 3.5h is reacted after being warmed to room temperature, is slowly added to 3mol/L
NaOH solution, continue to be slowly added to the hydrogen peroxide that mass fraction is 30%, it is suspended to obtain white by the reaction was continued at room temperature 10h
Liquid, adds ethyl acetate, and organic layer is washed with saturation NaCl, anhydrous Na SO4It is dry, solvent is evaporated off, residue crosses silica gel column layer
Analysis, petroleum ether：Ethyl acetate elutes, and obtains 5- isopropyl -9- hydroxyl -8- methyl -6- nonene -2- ketone condensed ethandiols, 5- isopropyls
The structural formula of base -9- hydroxyl -8- methyl -6- nonene -2- ketone condensed ethandiols is as follows：
；
（3）By step（2）Obtained 5- isopropyls -9- hydroxyls -8- methyl -6- nonene -2- ketone condensed ethandiols are dissolved in anhydrous
CH2Cl2, triethylamine is added, oxalyl chloride is slow added at 0 DEG C, is warmed to room temperature lower reaction 3.5h, ethyl acetate dilution is added, has
Machine layer is washed with saturation NaCl, anhydrous Na SO4It is dry, solvent is evaporated off, residue crosses silica gel column chromatography, petroleum ether：Ethyl acetate
Elution, obtains 5- isopropyl -9- hydroxyl -8- methyl -6- nonene -2- ketone oxalic acid dibasic acid esters, 5- isopropyl -9- hydroxyl -8- methyl -6-
The structural formula of nonene -2- ketone oxalic acid dibasic acid esters is as follows：
；
Synthetic route is as follows：
。
3. the synthesis side of 5- isopropyls -9- hydroxyls -8- methyl -6- nonene -2- ketone oxalic acid dibasic acid esters according to claim 2
Method, it is characterised in that：The step（1）Middle solanone, ethylene glycol, the ratio between the amount of material of p-methyl benzenesulfonic acid three are 1：1.5：
0.1。
4. the synthesis side of 5- isopropyls -9- hydroxyls -8- methyl -6- nonene -2- ketone oxalic acid dibasic acid esters according to claim 2
Method, it is characterised in that：The step（2）The ratio between middle solanone condensed ethandiol and amount of material of monoborane tetrahydrofuran complex are
1:1.5, it is necessary to 1 mL of NaOH solution, 1 mL of hydrogen peroxide on the basis of 1 mmol solanone condensed ethandiols.
5. the synthesis side of 5- isopropyls -9- hydroxyls -8- methyl -6- nonene -2- ketone oxalic acid dibasic acid esters according to claim 2
Method, it is characterised in that：The step（3）Middle 5- isopropyls -9- hydroxyls -8- methyl -6- nonene -2- ketone condensed ethandiol, triethylamine
It is 1 with the ratio between the amount of material of oxalyl chloride：1.2：0.5.
6. the 5- isopropyl -9- hydroxyl -8- methyl -6- nonene -2- ketone oxalic acid dibasic acid esters described in claim 1 is mixed with stabilizer or dilute
Release the application as spices in cigarette after agent.
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| CN201610571947.7A CN105968009B (en) | 2016-07-20 | 2016-07-20 | 5 isopropyl, 9 hydroxyl, 8 methyl, 6 nonene, 2 ketone oxalic acid dibasic acid esters and its synthetic method and application |
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| CN201610571947.7A CN105968009B (en) | 2016-07-20 | 2016-07-20 | 5 isopropyl, 9 hydroxyl, 8 methyl, 6 nonene, 2 ketone oxalic acid dibasic acid esters and its synthetic method and application |
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4489009A (en) * | 1982-03-11 | 1984-12-18 | International Flavors & Fragrances Inc. | Process for producing solanone, norsolanadione and intermediates therefor |
| US4784803A (en) * | 1986-06-30 | 1988-11-15 | Farmitalia Carlo Erba S.P.A. | Chemiluminescent composition, and a reactive component suitable for such a composition |
| CN1583711A (en) * | 2004-06-11 | 2005-02-23 | 长沙卷烟厂 | Oxalate for preparing ambrox or releasing ambrox in cigarette smoke and its use |
| CN102304155A (en) * | 2011-09-05 | 2012-01-04 | 川渝中烟工业公司 | Monosaccharide geraniol carbonate diester compound, preparation method and use thereof |
| CN103804508A (en) * | 2014-03-03 | 2014-05-21 | 河南中烟工业有限责任公司 | Preparation method and application of tobacco polysaccharide sulfate |
-
2016
- 2016-07-20 CN CN201610571947.7A patent/CN105968009B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4489009A (en) * | 1982-03-11 | 1984-12-18 | International Flavors & Fragrances Inc. | Process for producing solanone, norsolanadione and intermediates therefor |
| US4784803A (en) * | 1986-06-30 | 1988-11-15 | Farmitalia Carlo Erba S.P.A. | Chemiluminescent composition, and a reactive component suitable for such a composition |
| CN1583711A (en) * | 2004-06-11 | 2005-02-23 | 长沙卷烟厂 | Oxalate for preparing ambrox or releasing ambrox in cigarette smoke and its use |
| CN102304155A (en) * | 2011-09-05 | 2012-01-04 | 川渝中烟工业公司 | Monosaccharide geraniol carbonate diester compound, preparation method and use thereof |
| CN103804508A (en) * | 2014-03-03 | 2014-05-21 | 河南中烟工业有限责任公司 | Preparation method and application of tobacco polysaccharide sulfate |
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| Title |
|---|
| Tobacco chemistry. 63. Syntheses and stereostructures of six tobacco seco-cembranoids;Wahlberg,Inger等;《Acta Chemica Scandinavica》;19861231;第B40卷(第2期);第123-134页 * |
| 茄酸和茄酸乙酯的全合成研究;毛多斌;《香料香精化妆品》;20001231(第1期);第9-13页 * |
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