Alternatived Products of [ 15356-60-2 ]
Product Details of [ 15356-60-2 ]
| CAS No. : | 15356-60-2 |
MDL No. : | MFCD00062983 |
| Formula : |
C10H20O
|
Boiling Point : |
- |
| Linear Structure Formula : | - |
InChI Key : | - |
| M.W : |
156.27
|
Pubchem ID : | - |
| Synonyms : |
D-Menthol
|
Application In Synthesis of [ 15356-60-2 ]
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
- Upstream synthesis route of [ 15356-60-2 ]
- Downstream synthetic route of [ 15356-60-2 ]
- 1
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[ 75-44-5 ]
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[ 15356-60-2 ]
-
[ 7635-54-3 ]
- 2
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[ 29800-89-3 ]
-
[ 15356-60-2 ]
-
[ 130276-00-5 ]
- 3
-
[ 40834-42-2 ]
-
[ 15356-60-2 ]
-
[ 120263-06-1 ]
-
[ 120263-07-2 ]
- 4
-
[ 15356-60-2 ]
-
[ 601-75-2 ]
-
[ 122937-58-0 ]
- 5
-
[ 15356-60-2 ]
-
[ 601-75-2 ]
-
[ 111042-75-2 ]
-
[ 122937-58-0 ]
- 6
-
[ 80-59-1 ]
-
[ 15356-60-2 ]
-
[ 137693-54-0 ]
| Yield | Reaction Conditions | Operation in experiment |
| 95% |
With p-nitrobenzoic anhydride; scandium tris(trifluoromethanesulfonate) In nitromethane for 2h; Ambient temperature; |
|
| 95% |
With p-nitrobenzoic anhydride; scandium tris(trifluoromethanesulfonate) In nitromethane; acetonitrile for 2h; Ambient temperature; |
|
Reference：
[1]Ishihara, Kazuaki; Kubota, Manabu; Kurihara, Hideki; Yamamoto, Hisashi
[Journal of the American Chemical Society, 1995, vol. 117, # 15, p. 4413 - 4414]
[2]Ishihara, Kazuaki; Kubota, Manabu; Kurihara, Hideki; Yamamoto, Hisashi
[Journal of Organic Chemistry, 1996, vol. 61, # 14, p. 4560 - 4567]
- 7
-
[ 15356-60-2 ]
-
[ 1538-75-6 ]
-
[ 137601-34-4 ]
| Yield | Reaction Conditions | Operation in experiment |
| 99% |
With erbium(III) chloride at 50℃; for 6h; |
|
| 95% |
With scandium tris(trifluoromethanesulfonate) In acetonitrile for 1h; Ambient temperature; |
|
| 95% |
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 20℃; for 0.166667h; |
|
| 91% |
Stage #1: 2,2-dimethylpropanoic anhydride With molybdenium(VI) dioxodichloride In dichloromethane at 20℃; for 0.5h;
Stage #2: (1S,2R,5S)-(+)-menthol In dichloromethane at 20℃; for 40h; |
|
|
In acetonitrile at 20℃; for 0.583333h; |
|
Reference：
[1]Dalpozzo, Renato; De Nino, Antonio; Maiuolo, Loredana; Oliverio, Manuela; Procopio, Antonio; Russo, Beatrice; Tocci, Amedeo
[Australian Journal of Chemistry, 2007, vol. 60, # 1, p. 75 - 79]
[2]Ishihara, Kazuaki; Kubota, Manabu; Kurihara, Hideki; Yamamoto, Hisashi
[Journal of the American Chemical Society, 1995, vol. 117, # 15, p. 4413 - 4414]
Ishihara, Kazuaki; Kubota, Manabu; Kurihara, Hideki; Yamamoto, Hisashi
[Journal of Organic Chemistry, 1996, vol. 61, # 14, p. 4560 - 4567]
[3]Procopiou, Panayiotis A.; Baugh, Simon P.D.; Flack, Stephen S.; Inglis, Graham G.A.
[Journal of Organic Chemistry, 1998, vol. 63, # 7, p. 2342 - 2347]
[4]Chen, Chien-Tien; Kuo, Jen-Huang; Pawar, Vijay D.; Munot, Yogesh S.; Weng, Shieu-Shien; Ku, Cheng-Hsiu; Liu, Cheng-Yuan
[Journal of Organic Chemistry, 2005, vol. 70, # 4, p. 1188 - 1197]
[5]Procopio, Antonio; Dalpozzo, Renato; De Nino, Antonio; Maiuolo, Loredana; Russo, Beatrice; Sindona, Giovanni
[Advanced Synthesis and Catalysis, 2004, vol. 346, # 12, p. 1465 - 1470]
- 8
-
[ 15356-60-2 ]
-
[ 3333-15-1 ]
-
(2S)-2,3-Diphenyl-propansaeure-(-)-menthyl-(3)-ester
[ No CAS ]
- 9
-
[ 85-44-9 ]
-
[ 15356-60-2 ]
-
[ 53623-42-0 ]
| Yield | Reaction Conditions | Operation in experiment |
|
With N-ethyl-N,N-diisopropylamine In dichloromethane |
|
- 10
-
[ 15356-60-2 ]
-
[ 814-68-6 ]
-
[ 108945-28-4 ]
| Yield | Reaction Conditions | Operation in experiment |
| 95% |
With triethylamine In tetrahydrofuran at 0 - 20℃; for 24h; |
|
| 86% |
With triethylamine In tetrahydrofuran at 0℃; for 4h; |
(1S,2R,5S)-2-Isopropyl-5-methylcyclohexyl acrylate (d-menthyl acrylate, 17D)
To a stirred solution of d-(-)-menthol (75.0 g, 480 mmol) in THF (480 mL) at 0 °C was addedacryloyl chloride (47.0 mL, 576 mmol) and TEA (100 mL, 720 mmol). After stirring for 4 h,acetic acid buffer (pH 4.0, 200 mL) was added to the reaction mixture, which was thenextracted with Et2O (3 × 100 mL). The combined extracts were washed with brine (100 mL),dried over Na2SO4, and concentrated under reduced pressure. The residue was purified bycolumn chromatography on silica gel (500 g, toluene) to give d-menthyl acrylate (17D, 86.6g, 86%) as a colorless oil |
| 72% |
With pyridine In n-heptane 1.) 0 deg C, 30 min, 2.) room temperature, 3 h; |
|
| 68% |
With triethylamine In tetrahydrofuran |
|
|
With triethylamine at 0℃; for 4h; |
|
|
With triethylamine In dichloromethane at 20℃; for 5h; |
|
Reference：
[1]Kudryavtsev, Konstantin V.; Ivantcova, Polina M.; Muhle-Goll, Claudia; Churakov, Andrei V.; Sokolov, Mikhail N.; Dyuba, Artem V.; Arutyunyan, Alexander M.; Howard, Judith A. K.; Yu, Chia-Chun; Guh, Jih-Hwa; Zefirov, Nikolay S.; Bräse, Stefan
[Organic Letters, 2015, vol. 17, # 24, p. 6178 - 6181]
[2]Oikawa, Masato; Sugeno, Yuka; Tukada, Hideyuki; Takasaki, Yuichi; Takamizawa, Satoshi; Irie, Raku
[Bulletin of the Chemical Society of Japan, 2019, vol. 92, # 11, p. 1816 - 1823]
[3]Lee-Ruff, Edward; Xi, Feng-De; Qie, Jiang Hua
[Journal of Organic Chemistry, 1996, vol. 61, # 4, p. 1547 - 1550]
[4]He, Ke; Zhou, Zhenghong; Zhao, Guofeng; Tang, Chuchi
[Heteroatom Chemistry, 2006, vol. 17, # 4, p. 317 - 321]
[5]Manickum, Thavrin; Ross, Gregory H. P.
[South African Journal of Chemistry, 1994, vol. 47, # 1, p. 1 - 16]
[6]Kumar, Manoj; Verma, Akhilesh K.; Verma, Shalini
[Organic Letters, 2020]
- 11
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[ 15356-60-2 ]
-
[ 68766-96-1 ]
-
(R)-5-Oxo-pyrrolidine-2-carboxylic acid (1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl ester
[ No CAS ]
- 12
-
[ 32315-10-9 ]
-
[ 15356-60-2 ]
-
[ 7635-54-3 ]
| Yield | Reaction Conditions | Operation in experiment |
| 99% |
With pyridine; In dichloromethane; at -5 - 25℃; for 13h; |
General procedure: In a jacketed reactor equipped with a mechanical stirrer, a thermometer, a constant pressure dropping funnel and an exhaust gas absorber,Add 7L dichloromethane, the first reaction phase, temperature -5 C,780 g (5 mol) of L-menthol and 1187 g (4 mol) of triphosgene were added in portions and sufficiently stirred to dissolve them.-5 CDrop under the drop1215 g (12mo 1) triethylamine in methylene chloride (1.8 L) was added dropwise over 1 to 2 h,Insulation reaction 3h after the natural temperature rise to the second reaction stage, temperature control 25 C, stirring about 10h.After completion of the reaction, the reaction mixture was separated by filtration under filtration, and the mother liquor was washed successively with 3 L of water, 3 L of dilute hydrochloric acid (5%), 0.5 L of sodium carbonate (5%) and 0.5 L of saturated brine ,After drying over anhydrous sodium sulfate, the solvent was removed by steaming and distilled under reduced pressure to collect 108 to 109 C / 1 ImmHg fraction,1063 g of a colorless liquid was obtained in a yield of 97.2%. |
- 13
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[ 15356-60-2 ]
-
[ 149814-40-4 ]
-
[ 400724-24-5 ]
| Yield | Reaction Conditions | Operation in experiment |
| 86% |
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; |
|
- 14
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[ 15356-60-2 ]
-
[ 16404-94-7 ]
-
(S)-4-Oxo-azetidine-2-carboxylic acid (1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl ester
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 28% |
With dmap; dicyclohexyl-carbodiimide In dichloromethane; acetonitrile at 0 - 20℃; |
|
- 15
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[ 108-22-5 ]
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[ 15356-70-4 ]
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[ 15356-60-2 ]
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[ 2216-51-5 ]
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[ 5157-89-1 ]
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[ 2623-23-6 ]
| Yield | Reaction Conditions | Operation in experiment |
|
With lipase from Pseudomonas cepacia immobilized on ceramic In toluene at 40℃; for 15h; Title compound not separated from byproducts; |
|
|
With Pseudomonas cepacia lipase; 4 A molecular sieve; peracetylated β-cyclodextrin In toluene at 40℃; for 2h; Title compound not separated from byproducts; |
|
|
With Pseudomonas cepacia lipase; 4 A molecular sieve; peracetylated β-cyclodextrin In toluene at 40℃; for 8h; Title compound not separated from byproducts; |
|
Reference：
[1]Ghanem, Ashraf; Schurig, Volker
[Monatshefte fur Chemie, 2003, vol. 134, # 8, p. 1151 - 1157]
[2]Ghanem, Ashraf; Schurig, Volker
[Tetrahedron Asymmetry, 2003, vol. 14, # 17, p. 2547 - 2555]
[3]Ghanem, Ashraf; Schurig, Volker
[Tetrahedron Asymmetry, 2003, vol. 14, # 17, p. 2547 - 2555]
- 16
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[ 108-05-4 ]
-
[ 15356-70-4 ]
-
[ 15356-60-2 ]
-
[ 2216-51-5 ]
-
[ 2623-23-6 ]
| Yield | Reaction Conditions | Operation in experiment |
| 1: 39%
2: 88 % ee |
With Candida cylindracea lipase; quinidine In tert-butyl methyl ether at 20℃; for 48h; Resolution of racemate; Enzymatic reaction; |
Enzymatic acylation with enol esters
To 1 mmol of racemic alcohol (1), 3 mmol of the appropriate enol ester (isopropenyl acetate or vinyl acetate) and a catalytic amount of lipase were dissolved in 2 mL of organic solvent. The suspension was stirred at room temperature for the indicated time. The reaction mixture was filtered on Celite and concentrated in vacuum. The remaining alcohol and the produced acetate were separated by chromatography on silica gel (petroleum ether/ethyl acetate: 95/5) and analyzed by chiral GC. The same procedure was followed for the reactions in the presence of 30 mol% of additives. |
|
With Pseudomonas cepacia lipase In various solvent(s) at 20℃; |
|
Reference：
[1]Belkacemi, Fatima Zohra; Merabet-Khelassi, Mounia; Aribi-Zouioueche, Louisa; Riant, Olivier
[Research on Chemical Intermediates, 2018, vol. 44, # 11, p. 6847 - 6860]
[2]Serra, Stefano; Brenna, Elisabetta; Fuganti, Claudio; Maggioni, Francesco
[Tetrahedron Asymmetry, 2003, vol. 14, # 21, p. 3313 - 3319]
- 17
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[ 15356-60-2 ]
-
[ 59760-01-9 ]
-
[ 872619-06-2 ]
- 18
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[ 15356-60-2 ]
-
[ 2873-29-2 ]
-
(1S,2R,5S)-menthyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 84% |
With carbon immobilized iron (III) chloride hexahydrate In dichloromethane at 20℃; for 1h; stereoselective reaction; |
General Experimental Procedure for the Synthesisof 2,3-Unsaturated Glucosides
General procedure: To a stirred solution of tri-O-acetyl-D-glucal (100 mg, 0.37 mmol) in DCM(1 mL) were added the corresponding alcohol (0.41 mmol, 1.1 equiv) andFeCl3·6H2O/C (5 mol%) at ambient temperature. After the reaction was completed(monitored by TLC), the reaction mixture was filtered and the catalystwas washed with dichloromethane. After evaporation of the solvent under vacuum,the crude products were purified by silica gel column chromatography(petroleum ether/EtOAc = 10/1). |
| 77% |
With niobium pentachloride In dichloromethane at 20℃; for 1h; |
|
Reference：
[1]Zhou, Jiafen; Chen, Heshan; Shan, Junjie; Li, Juan; Yang, Guofang; Chen, Xuan; Xin, Kunyun; Zhang, Jianbo; Tang, Jie
[Journal of Carbohydrate Chemistry, 2014, vol. 33, # 6, p. 313 - 325]
[2]de Oliveira, Ronaldo N.; de Melo, Adriana C.N.; Srivastava, Rajendra M.; Sinou, Denis
[Heterocycles, 2006, vol. 68, # 12, p. 2607 - 2613]
- 19
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[ 15356-60-2 ]
-
[ 16052-40-7 ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: 91 percent / Lucas-reagent
2: 1) Mg, 1,2-dibromoethane / 1) diethyl ether, 2 h, reflux, 2) 1/2 h |
|
- 20
-
[ 1001067-09-9 ]
-
[ 15356-60-2 ]
-
[ 1001067-31-7 ]
| Yield | Reaction Conditions | Operation in experiment |
| 97% |
With triethylamine In dichloromethane at 20℃; for 0.0833333h; |
|
- 21
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[ 15356-60-2 ]
-
[ 1212-53-9 ]
-
[ 1038873-34-5 ]
- 22
-
[ 15356-60-2 ]
-
[ 3731-16-6 ]
-
[ 1345459-39-3 ]
| Yield | Reaction Conditions | Operation in experiment |
|
With dmap; In toluene; for 168h;Reflux; |
4-Dimethylaminopyridine (0.35wt), (+)-menthol (0.95wt) and ethyl 2-oxo-3- piperidinecarboxylate (1wt) are dissolved/suspended in toluene (10vol). The mixture is heated to reflux and stirred for seven days with periodic distillation of solvent and replenishment with fresh toluene. The reaction mixture is cooled to 25C and washed with two portions of 5%w/w aqueous HCI (4 vol) and then water (4 vol). The organic phase is concentrated under reduced pressure to give the title compound as a colourless oil. |
|
With dmap; In toluene;Reflux; |
Stage a) Preparation of (1S,2R,5S)-5-methyl-2-(1-methylethyl)cyclohexyl 2-oxo-3-piperidinecarboxylate 4-Dimethylaminopyridine (0.35 wt), (+)-menthol (0.95 wt) and ethyl 2-oxo-3-piperidinecarboxylate (1 wt) are dissolved/suspended in toluene (10 vol). The mixture is heated to reflux and stirred for seven days with periodic distillation of solvent and replenishment with fresh toluene. The reaction mixture is cooled to 25 C. and washed with two portions of 5% w/w aqueous HCl (4 vol) and then water (4 vol). The organic phase is concentrated under reduced pressure to give the title compound as a colourless oil. |
- 23
-
[ 227626-60-0 ]
-
[ 15356-60-2 ]
-
[ 1554303-43-3 ]
| Yield | Reaction Conditions | Operation in experiment |
| 91% |
|
General procedure: To a solution of <strong>[227626-60-0]2-(1-(((tert-butoxycarbonyl)amino)methyl)cyclohexyl)acetic acid</strong> 16c (0.50 g, 1.84 mmol) in dry THF (30 mL)N-methylmorpholine was added (0.20 mL, 1.84 mmol) and the mixture was stirred at rt for 10min under nitrogen. After cooling to 0 C,isobutyl chloroformate (0.18 mL, 1.84mmol) was added dropwise.N-Methylmorpholine (0.20 mL, 1.84 mmol) was then added in 4 min followed by the addition of nucleophile (1.84 mmol) then stirred for 24 h at rt under nitrogen. After the solvent was evaporated, ethyl acetate (30 mL) was added to the crude and solution was washed with 2 N HCl solution (2 x 50 mL) and saturated sodium carbonate solution (2 30 mL). The organic phasewas dried over anhyd magnesium sulfate and solvent was removed to give the desired product. |
- 24
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[ 15356-60-2 ]
-
[ 4098-06-0 ]
-
methyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-threo-hex-2-enopyranoside
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 67% |
With carbon immobilized iron (III) chloride hexahydrate In dichloromethane at 20℃; for 1.5h; stereoselective reaction; |
General Experimental Procedure for the Synthesis of2,3-Unsaturated Galactosides
General procedure: To a stirred solution of tri-O-acetyl-D-galactal (50 mg, 0.185 mmol) in DCM(1 mL) were added the corresponding alcohol (0.204 mmol, 1.1 equiv) andFeCl3·6H2O/C (50 mol%) at ambient temperature. After the reaction was completed(monitored by TLC), the reaction mixture was filtered and the catalystwas washed with dichloromethane. After evaporation of the solvent under vacuum,the crude products were purified by silica gel column chromatography(petroleum ether/EtOAc = 10/1). |
Reference：
[1]Zhou, Jiafen; Chen, Heshan; Shan, Junjie; Li, Juan; Yang, Guofang; Chen, Xuan; Xin, Kunyun; Zhang, Jianbo; Tang, Jie
[Journal of Carbohydrate Chemistry, 2014, vol. 33, # 6, p. 313 - 325]
- 25
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[ 15356-60-2 ]
-
[ 2528-61-2 ]
-
Heptanoic acid (1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl ester
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 91% |
With thionyl chloride In tetrahydrofuran for 3h; |
3 Example 3:
Take 26 g (0.2 mol) of heptanoic acid,17.85 g (0.15 mol) of thionyl chloride was added,After mixing, the reaction was carried out at 60 ° C for 3 hours,20 ml of a tetrahydrofuran solution containing 15.3 g (0.1 mol) of d-menthol was added,The reaction was continued for 3 hours,The reaction solution was adjusted to pH 6 to 7 with NaOH solution,The organic layer was separated and the aqueous layer was extracted with ethyl acetate,The organic layers were combined, washed with saturated brine,Dried over anhydrous Na2SO4 overnight, the solvent evaporated,Column chromatography (silica gel 200 ~ 300 mesh),B petroleum ether and ethyl acetate (15: 1 volume ratio) as eluent,The eluent was distilled off to give 24.41 g of a colorless liquid,Yield: 91%. |
- 26
-
[ 15356-60-2 ]
-
[ 74808-09-6 ]
-
[ 907606-02-4 ]
| Yield | Reaction Conditions | Operation in experiment |
| 61% |
Stage #1: (1S,2R,5S)-(+)-menthol; 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl trichloroacetimidate With 1,3-bis(3,5-bis(trifluoro-ethyl)phenyl)thiourea In dichloromethane at 20℃; for 0.166667h; Molecular sieve; Inert atmosphere; Green chemistry;
Stage #2: With 3,5-di(methoxycarbonyl)-N-(cyanomethyl)pyridinium bromide In dichloromethane at 20℃; for 4h; Molecular sieve; Inert atmosphere; Green chemistry; |
(a) Normal procedure:
General procedure: To a stirred suspension of trichloroacetimidate donor (0.15 mmol, 1.0equiv), acceptor (0.165 mmol, 1.1 equiv) and 4 Å MS (200 mg) in dry DCM (3 ml) was added aryl thiourea 4 (0.015 mmol, 0.1 equiv) at room temperature. The mixture was stirred for 10 min at room temperature under a nitrogen atmosphere. Then, electron-deficient pyridinium salt (0.015 mmol, 0.1 equiv) was added and the resulting reaction mixture was stirred at room temperature until total consumption of glycosyl donor monitored by TLC. After completion of reaction, the mixture was concentrated in vacuo and purified by column chromatography using different fractions of acetone in hexane as eluting solvent to afford the desired glycosides. |
- 27
-
[ 36821-26-8 ]
-
[ 15356-60-2 ]
-
(1S,2R,5S)-2-isopropyl-5-methylcyclohexyl 2-oxopyrrolidine-3-carboxylate
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 100% |
With dmap In toluene for 72h; Reflux; Dean-Stark; |
I ntermediate 1: (1 S.2R.5S-2-isopropyI-5-methyIcycIohexyI 2-oxopyrrolidine-3- carboxylate (Compound XI X
A solution of (+)-Menthol (5.12 g, 32.8 mmol) (available from Alfa Aesar), ethyl 2- oxopyrrolidine-3-carboxylate (5 g, 31.8 mmol) (available from Aldrich), and DMAP (1.943 g, 15.91 mmol) in toluene (40 mL) was heated to reflux in a Dean Stark apparatus for 72 h with periodic removal of condensed toluene/ethanol mixture and replacement with equal quantity of toluene. Thesolution was cooled and treated with aqueous 2M hydrochloric acid solution (100 mL) and ethyl acetate (100 mL). The layers were separated and the organic layer concentrated in vacua to give a yellow oil. The crude oil was subjected to column chromatography (silica 330g, 0 to 100% TBME in cyclohexane over bOys, visualised at 220 nm). The relevant fractions were combined and concentrated in vacuagive the title campaund(8.494 g, 100 %) as a colourless oil: LCMS (System C) RT= 1.17 mi ES÷ yem/z268(M+H). |
- 28
-
[ 108-22-5 ]
-
[ 15356-70-4 ]
-
[ 15356-60-2 ]
-
[ 2216-51-5 ]
-
[ 2623-23-6 ]
| Yield | Reaction Conditions | Operation in experiment |
| 1: 32%
2: 66 % ee |
With Candida cylindracea lipase In diethyl ether at 20℃; for 48h; Resolution of racemate; Enzymatic reaction; |
Enzymatic acylation with enol esters
To 1 mmol of racemic alcohol (1), 3 mmol of the appropriate enol ester (isopropenyl acetate or vinyl acetate) and a catalytic amount of lipase were dissolved in 2 mL of organic solvent. The suspension was stirred at room temperature for the indicated time. The reaction mixture was filtered on Celite and concentrated in vacuum. The remaining alcohol and the produced acetate were separated by chromatography on silica gel (petroleum ether/ethyl acetate: 95/5) and analyzed by chiral GC. The same procedure was followed for the reactions in the presence of 30 mol% of additives. |
- 29
-
[ 108-05-4 ]
-
[ 15356-70-4 ]
-
[ 15356-60-2 ]
-
[ 2216-51-5 ]
-
[ 5157-89-1 ]
-
[ 2623-23-6 ]
| Yield | Reaction Conditions | Operation in experiment |
| 1: 9 % ee
2: 27 % ee |
With Candida cylindracea lipase; quinidine In n-heptane at 20℃; for 48h; Resolution of racemate; Enzymatic reaction; |
Enzymatic acylation with enol esters
To 1 mmol of racemic alcohol (1), 3 mmol of the appropriate enol ester (isopropenyl acetate or vinyl acetate) and a catalytic amount of lipase were dissolved in 2 mL of organic solvent. The suspension was stirred at room temperature for the indicated time. The reaction mixture was filtered on Celite and concentrated in vacuum. The remaining alcohol and the produced acetate were separated by chromatography on silica gel (petroleum ether/ethyl acetate: 95/5) and analyzed by chiral GC. The same procedure was followed for the reactions in the presence of 30 mol% of additives. |
- 30
-
[ 108-05-4 ]
-
[ 15356-70-4 ]
-
[ 15356-60-2 ]
-
[ 5157-89-1 ]
-
[ 2623-23-6 ]
| Yield | Reaction Conditions | Operation in experiment |
| 1: 75 % ee
2: 42% |
With Candida cylindracea lipase; quinidine In diethyl ether at 20℃; for 48h; Resolution of racemate; Enzymatic reaction; |
Enzymatic acylation with enol esters
To 1 mmol of racemic alcohol (1), 3 mmol of the appropriate enol ester (isopropenyl acetate or vinyl acetate) and a catalytic amount of lipase were dissolved in 2 mL of organic solvent. The suspension was stirred at room temperature for the indicated time. The reaction mixture was filtered on Celite and concentrated in vacuum. The remaining alcohol and the produced acetate were separated by chromatography on silica gel (petroleum ether/ethyl acetate: 95/5) and analyzed by chiral GC. The same procedure was followed for the reactions in the presence of 30 mol% of additives. |
- 31
-
[ 108-30-5 ]
-
[ 15356-70-4 ]
-
[ 15356-60-2 ]
-
[ 2216-51-5 ]
-
[ 77341-67-4 ]
-
[ 204326-53-4 ]
| Yield | Reaction Conditions | Operation in experiment |
|
With Candida cylindracea lipase; In diethyl ether; at 20℃; for 24.0h;Schlenk technique; Resolution of racemate; Enzymatic reaction; |
A dry Schlenk tube was charged with rac-alcohol (1 equivalent) and succinic anhydride (1 equiv.) dissolved in 2 mL of diethyl ether. The reaction was initiated by the addition of 100 mg of CCL. The reaction mixture was shaken at room temperature for 24 h. After removal of the lipase by filtration, the filtrate was shaken with 1 M Na2CO3 solution, and the remaining alcohol and the produced monoester succinate were separated by liquid-liquid extraction. The remaining enantiomer was obtained from the organic layer and the aqueous phase was washed with an organic solvent and treated by adding 1 M NaOH solution to obtain the other enantiomer. The enantiomeric excesses values were quantified by chiral GC analyses. Chiral GC: Chiralsil-DEX CB: (Tcolumn = 120 C. flow: 1,2 mL/min); dl-(±)-menthyl acetate: td-(+) = 9.58 min; tl-(-) =10.85 min. dl-(±)-menthol: td-(+) = 13.25 min; tl-(-) = 13.69 min. |
- 32
-
[ 15356-60-2 ]
-
[ 121-34-6 ]
-
(1S,2R,5S)-2-isopropyl-5-methylcyclohexyl 4-hydroxy-3-methoxybenzoate
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 93% |
With sulfuric acid-immobilized mesoporous silica catalyst at 80℃; for 3h; Green chemistry; |
2.3. Synthesis of Phenolic Ester Aglycones.
General procedure: Phenolic acids(1a-d) (1 mmol each), menthol (2) (0.468 g, 3 mmol) and Si-H+ catalyst (0.294 g, 0.3 mole%) were stirred at 80-100°C for2.5 hours. TLC assisted to observe reaction progress using30% ethyl acetate and n-hexane as eluent. After reaction completion, the contents were dissolved in ethyl acetate, |
- 33
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[ 15356-60-2 ]
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[ 201851-49-2 ]
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[ CAS Unavailable ]
| Yield | Reaction Conditions | Operation in experiment |
| 88% |
Stage #1: (+)-Menthol With sodium hydride In tetrahydrofuran; hexane at 20℃; for 0.5h; Inert atmosphere;
Stage #2: 2,2'-bis(2-fluorophenyl)-4,4',5,5'-tetrahydro-4,4'-bioxazole In tetrahydrofuran; hexane Inert atmosphere; Reflux; |
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