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CAS No. : | 10482-56-1 | MDL No. : | MFCD00075926 |
Formula : | C10H18O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | WUOACPNHFRMFPN-SECBINFHSA-N |
M.W : | 154.25 | Pubchem ID : | 443162 |
Synonyms : |
α-Terpineol;(S)-α-Terpineol;HSDB 2683;L-alpha-Terpineol;EINECS 233-986-8;(L)-alpha-Terpineol
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.8 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 48.8 |
TPSA : | 20.23 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -4.83 cm/s |
Log Po/w (iLOGP) : | 2.09 |
Log Po/w (XLOGP3) : | 3.39 |
Log Po/w (WLOGP) : | 2.5 |
Log Po/w (MLOGP) : | 2.3 |
Log Po/w (SILICOS-IT) : | 2.17 |
Consensus Log Po/w : | 2.49 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.87 |
Solubility : | 0.21 mg/ml ; 0.00136 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.49 |
Solubility : | 0.0495 mg/ml ; 0.000321 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -1.69 |
Solubility : | 3.17 mg/ml ; 0.0206 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 3.24 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P210-P264-P273-P280-P302+P352-P305+P351+P338-P312-P332+P313-P337+P313-P370+P378-P403+P235-P501 | UN#: | N/A |
Hazard Statements: | H227-H302-H315-H319-H402 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | To a solution of (-)-menthol (22 mg, 0.143 mmol) in 1 mL of THF at -45 C was added dropwise 0.143 mL of a 1.0 M solution of lithium hexamethyldisilazide in THF. After 1 h at -45 C, a solution of (+)-cis-1-benzoyl-3-(2-methoxy-2-propyloxy)-4-phenylazetidin-2-one (58 mg, 0.172 mmol) in 1 mL of THF was added dropwise to the mixture. The solution was warmed to 0 C and kept at that temperature for 2 h before 1 mL of a 10% solution of AcOH in THF was added. The mixture was partitioned between saturated aqueous NaHCO3 and 60/40 ethyl acetate/hexane. Evaporation of the organic layer gave 73 mg of a residue which was dissolved in 6 mL of THF at 0 C. To this solution was added 0.9 mL of glacial acetic acid and 0.9 mL of water. The mixture was stirred at 0 C for 3 h, then partitioned between saturated aqueous sodium bicarbonate and ethyl acetate. Evaporation of the ethyl acetate solution gave 70 mg of material which was purified by chromatography on silica gel to give 48 mg (80%) of a-terpineyl N-benzoyl-(2'R,3'S)-phenylisoserine ester. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With water;pH 2.5; | General procedure: Synthesized glycosides were subjected separately to the acid and enzymatic hydrolysis. 100 mg of each glycoside were weighted into a 100 ml volumetric flask and methanol was added to obtain a concentration of 1 mg/ml. 100 mul of this solution was transferred to a 40 ml screw cap vial and evaporated to dryness and subjected to hydrolysis. The reference sample was dissolved in 1 ml of methanol and analyzed by HPLC. The acid hydrolysis was performed using McIlvaine citric buffer (0.1 M, pH 2.5) in several variations: 100 C for 1 and 2 h, 80 C for 2 h, 60 C for 4 h, 40 C for 16 and 24 h. Enzymatic hydrolysis was performed using AR 2000 enzymatic preparation (Gist Brocades, The Netherlands) - 20 mg/1 ml of McIlvaine buffer (pH 5.5) at 40 C for 21 h. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol; at 20℃; for 168h; | General procedure: To the 0.01 M solution of beta-cyclodextrin (10 mL) the solutionof (+)- or (-)-alpha-terpineol (15.4 mg, 0.01 mM) in methanol (0.5 mL)was added and the obtained solution was left at RT. Monocrystals appropriate for X-ray measurement were obtained after one week. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With N-Bromosuccinimide; water; In acetone; | General procedure: In a flask, olefin and NBS (1:1.2) were mixed with 15%aqueous acetone and allowed for stirring until completion of reaction by TLC. Upon completion of reaction, acetonewas removed by flash evaporation and diluted withwater. Extraction with DCM (3 times) and its concentrationafforded crude product, which was purified bycolumn chromatography. The pure compounds werecharacterised by spectral studies and compared withthose from literature in case of 1 and 2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ammonium cerium (IV) nitrate; In methanol; at 0 - 20℃;Inert atmosphere; | General procedure: To a stirred solution of 1, 4, or 6 (2.0 mmol) and corresponding alkenol (2.2 mmol) in 10 cm3 MeOH or 10 cm3 MeCN (for 6) at 0 C under Ar was added dropwise solution of 2.35 g CAN (4.2 mmol) in 20 cm3 MeOH or 20 cm3 MeCN during 15 min. The mixture was then stirred at room temperature until the completion of reaction was confirmed by TLC (15-45 min). After addition of 20 cm3 water and removal of the organic solvent in vacuo, the residue was extracted with dichloromethane (3 9 15 cm3). Combined extracts were washed with 10 cm3 saturated solution of NaHCO3 and 10 cm3 brine and dried over anhydrous Na2SO4. Evaporation of the solvent gave a yellowish oil which was chromatographed on silica gel with n-hexane-AcOEt mixtures of increasing polarity (starting from 1:1). All the compounds synthesized were obtained as colorless oils. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81.64% | With thionyl chloride; N,N-dimethyl-formamide; In dichloromethane; at 0 - 5℃;Inert atmosphere; | Add raw material (I) (alpha-terpineol, 10 g, 64.83 mmol) to a 500 ml reaction flask at room temperature.And 100 ml of dichloromethane,Stir until completely dissolved, replace nitrogen, and lower the temperature to about 0 C;Add 1-2 drops of N, N-dimethylformamide,0 ~ 5 temperature was slowly added dropwise thionyl chloride (8.87g, 74.55mmol) was dissolved in 30ml of methylene chloride;After dripping, keep at 0 C ~ 5 C for 1 ~ 2 hours;TLC monitoring After the reaction of the raw materials is completed,Stop the reaction, naturally warm to room temperature, and add 260ml of water to quench the reaction.Separate the liquid phase and back extract with 70 ml of dichloromethane;Combine the organic phases, first wash with saturated sodium bicarbonate solution until weakly alkaline, then wash with saturated sodium chloride solution until neutral,Add 20g of anhydrous sodium sulfate and stir for 2 hours or more;Filtered, the filtrate was evaporated under reduced pressure,About 9.14 g of intermediate product (II) was obtained,The yield was 81.64%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With formic acid; dihydrogen peroxide; sodium hydroxide; In water; at 0℃; | We also prepared (-)-8 from (-)-alpha-terpineol according to the reported procedure [17].The identicalness of the absolute configurations of two synthetic(-)-8 was confirmed by chiral GLC analysis: 40%AcTBDMSBCD+10%PentylTBDMSBCD (30 m, ID0.25 mm, film 0.25 mum), tR = 183.5 min (major) andtR = 185.0 min (minor). |
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