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CAS No. : | 72345-23-4 | MDL No. : | MFCD00064276 |
Formula : | C5H12O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | GTCCGKPBSJZVRZ-WHFBIAKZSA-N |
M.W : | 104.15 | Pubchem ID : | 6950200 |
Synonyms : |
|
Num. heavy atoms : | 7 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 1.0 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 28.47 |
TPSA : | 40.46 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.88 cm/s |
Log Po/w (iLOGP) : | 1.49 |
Log Po/w (XLOGP3) : | 0.08 |
Log Po/w (WLOGP) : | 0.14 |
Log Po/w (MLOGP) : | 0.23 |
Log Po/w (SILICOS-IT) : | 0.03 |
Consensus Log Po/w : | 0.39 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -0.4 |
Solubility : | 41.1 mg/ml ; 0.394 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.48 |
Solubility : | 34.2 mg/ml ; 0.328 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | 0.07 |
Solubility : | 121.0 mg/ml ; 1.16 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.73 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | 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 |
---|---|---|
95% | With o-toluenesulfonic acid In toluene | |
95% | With toluene-4-sulfonic acid In toluene Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With boron trifluoride diethyl etherate In tetrahydrofuran for 16h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With toluene-4-sulfonic acid In dichloromethane Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82.9% | With collidinium p-toluene sulfonate In benzene for 48h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With pyridinium p-toluenesulfonate In benzene for 2h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With toluene-4-sulfonic acid In benzene at 75℃; for 0.5h; Yield given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran Linde 4A molecular sieves; Yield given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With sodium hydride In tetrahydrofuran for 2.75h; Ambient temperature; | |
With sodium hydride 1) THF, 2 h, RT, 2) THF, 45 min; Yield given. Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With pyridine In tetrahydrofuran a) 0 deg C to room temperature, b) overnight; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With hydrogenchloride; <NH2Et2><<RuCl(S-BINAP)>2(μ-Cl)3>; hydrogen In methanol at 60℃; for 0.666667h; other diones, also without HCl, var. time, temp. and pressure; | |
95% | With hydrogenchloride; <NH2Et2><<RuCl(S-BINAP)>2(μ-Cl)3>; hydrogen In methanol at 60℃; for 0.666667h; | |
44% | With hydrogen; acetic acid In tetrahydrofuran at 100℃; |
42% | With dichloro(benzene)ruthenium(II) dimer; hydrogen; (2S,4S)-2,4-bis(diphenylphosphino)pentane In methanol at 80℃; for 16h; | |
With <RuCl2(PPh3)><(S)-2,2'-dimethyl-6,6'-bis(diphenylphosphino)biphenyl>; hydrogen In ethanol at 40℃; for 60h; | ||
With hydrogen In methanol for 64h; Ambient temperature; | ||
With hydrogen bromide; hydrogen; (S)-5',6'-benzo-6-methoxy-2,2'-bis(diphenylphosphanyl)biphenyl In methanol at 50℃; for 72h; | ||
99 % ee | With hydrogenchloride; hydrogen In ethanol; water at 80℃; for 16.5h; | |
96 % ee | With hydrogenchloride; diiodo(p-cymene)ruthenium(II) dimer; (R)-1-{(RFc)-2-[2-(diphenylphosphino)phenyl]ferrocenyl}ethylbis[3,5-bis-(trifluoromethyl)phenyl]phosphine; hydrogen In methanol at 80℃; for 17h; Autoclave; enantioselective reaction; | |
98% ee | With hydrogenchloride; bis(norbornadiene)rhodium(l)tetrafluoroborate; (Sp)-2-[(R)-1-diphenylphosphinoethyl]-(Sp)-2″-diphenylphosphino-1,1″-biferrocene; hydrogen In methanol; water at 80℃; for 17h; Inert atmosphere; Autoclave; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80.2% | With triethylamine In dichloromethane at 0 - 20℃; | |
58% | With pyridine at 20℃; for 48h; Inert atmosphere; | |
49% | With pyridine |
In pyridine at 0℃; overnight; | ||
With pyridine |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 0.1 % Chromat. 2: 99.0 % Chromat. | With tetraphenylarsonium chloride; hydrogen In ethanol at 50℃; for 24h; Title compound not separated from byproducts; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With L-Tartaric acid; hydrogen In tetrahydrofuran; water | ||
With D-tartaric acid; hydrogen In tetrahydrofuran | ||
With hydrogen In methanol at 80℃; for 64h; Title compound not separated from byproducts; |
With chiral 1,5-diphenylphosphanylferrocene compound; hydrogen bromide; hydrogen In ethanol at 50℃; for 8h; | ||
With hydrogen In methanol at 80℃; for 17h; | ||
With hydrogenchloride; diiodo(p-cymene)ruthenium(II) dimer; (S(p),S(p))-2,2''-bis(diphenylphosphino)-1,1''-biferrocene; hydrogen In ethanol; water at 80℃; for 19h; Autoclave; optical yield given as %ee; enantioselective reaction; | ||
85 % ee | With hydrogenchloride; diiodo(p-cymene)ruthenium(II) dimer; (SFc)-2-{(R)-1-bis[3,5-bis(trifluoromethyl)phenyl]phosphinoethyl}-(RFc)-2′′-diphenylphosphino-1,1′′-biferrocene; hydrogen In methanol at 80℃; for 17h; Autoclave; | |
85 % ee | With hydrogenchloride; diiodo(p-cymene)ruthenium(II) dimer; (S)-1-{(SFc)-2-[2-(diphenylphosphino)phenyl]ferrocenyl}ethylbis[3,5-bis-(trifluoromethyl)phenyl]phosphine; hydrogen In methanol at 80℃; for 17h; Autoclave; | |
85% ee | With hydrogenchloride; bis(norbornadiene)rhodium(l)tetrafluoroborate; (R)-1-[2-(2'-diphenylphosphinophenyl)ferrocenyl]ethyldiphenylphosphine; hydrogen In methanol; water at 80℃; for 17h; Inert atmosphere; Autoclave; | |
80% ee | With hydrogenchloride; bis(norbornadiene)rhodium(l)tetrafluoroborate; (Sp)-2-[(R)-1-diphenylphosphinoethyl]-(Rp)-2″-diphenylphosphino-1,1″-biferrocene; hydrogen In methanol; water at 80℃; for 17h; Inert atmosphere; Autoclave; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With toluene-4-sulfonic acid In diethyl ether for 5h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With triethylamine; trichlorophosphate In benzene for 15h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In toluene |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With triethylamine; phosphorus trichloride In diethyl ether at -20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With toluene-4-sulfonic acid In benzene Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen In methanol at 80℃; for 60h; Title compound not separated from byproducts; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 10-undecenoic acid With thionyl chloride In N,N-dimethyl-formamide; benzene for 2h; Thermolysis; Stage #2: cycl-isopropylidene malonate With dmap In dichloromethane at 0 - 20℃; Stage #3: (2S,4S)-pentane-2,4-diol In benzene for 3h; Thermolysis; Title compound not separated from byproducts; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With pyridinium p-toluenesulfonate In benzene at 80℃; for 0.333333h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine In 1,2-dichloro-ethane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine In 1,2-dichloro-ethane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97.9% | With triethylamine In toluene at 0 - 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With triethylamine In toluene at 0 - 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In toluene at 0 - 20℃; Title compound not separated from byproducts; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93.1% | With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran for 24h; | |
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine; dmap at 20℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With toluene-4-sulfonic acid In benzene for 5h; Heating; | |
With pyridinium p-toluenesulfonate In toluene for 3.5h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With 2,6-dimethylpyridine In dichloromethane at -78℃; for 2.5h; | |
With 2,6-dimethylpyridine |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 20℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 20℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 20℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 20℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 2,6-lutidine 2: [(Me2N)2CNH2][N3] | ||
Multi-step reaction with 2 steps 1: 100 percent / 2,6-dimethylpyridine / CH2Cl2 / 2.5 h / -78 °C 2: 100 percent / [(Me2N)2CNH2]N3 / CH2Cl2 / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: 2,6-lutidine 2.1: [(Me2N)2CNH2][N3] 3.2: aq. NaOH | ||
Multi-step reaction with 3 steps 1.1: 100 percent / 2,6-dimethylpyridine / CH2Cl2 / 2.5 h / -78 °C 2.1: 100 percent / [(Me2N)2CNH2]N3 / CH2Cl2 / 0 - 20 °C 3.1: toluene / 24 h / 0 - 20 °C 3.2: 76 percent / MeOH / toluene / 0.75 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 90 percent / p-TsOH*H2O / benzene / 5 h / Heating 2: 73 percent / N-diisopropylethylamine; dppb / Pd(OAc)2 / dimethylsulfoxide / 100 °C 3: 32.6 percent / LiAlH4 / tetrahydrofuran; diethyl ether / 0.5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 90 percent / p-TsOH*H2O / benzene / 5 h / Heating 2: 73 percent / N-diisopropylethylamine; dppb / Pd(OAc)2 / dimethylsulfoxide / 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: 90 percent / p-TsOH*H2O / benzene / 5 h / Heating 2.1: 73 percent / N-diisopropylethylamine; dppb / Pd(OAc)2 / dimethylsulfoxide / 100 °C 3.1: 32.6 percent / LiAlH4 / tetrahydrofuran; diethyl ether / 0.5 h / 20 °C 4.1: KH / tetrahydrofuran / 1.5 h / -30 °C 4.2: tetrahydrofuran / 2 h / 20 °C 4.3: 36 percent / KH / tetrahydrofuran / 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: 90 percent / p-TsOH*H2O / benzene / 5 h / Heating 2.1: 73 percent / N-diisopropylethylamine; dppb / Pd(OAc)2 / dimethylsulfoxide / 100 °C 3.1: 32.6 percent / LiAlH4 / tetrahydrofuran; diethyl ether / 0.5 h / 20 °C 4.1: KH / tetrahydrofuran / 1.5 h / -30 °C 4.2: tetrahydrofuran / 2 h / 20 °C 4.3: 38 percent / KH / tetrahydrofuran / 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: 80.2 percent / Et3N / CH2Cl2 / 0 - 20 °C 2.1: K2CO3 / dimethylsulfoxide / 1 h / 20 °C 2.2: 41.7 percent / dimethylsulfoxide / 72 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: 80.2 percent / Et3N / CH2Cl2 / 0 - 20 °C 2.1: K2CO3 / dimethylsulfoxide / 1 h / 20 °C 2.2: 41.7 percent / dimethylsulfoxide / 72 h / 20 °C 3.1: 100 percent / bromine / acetic acid / 24 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: 80.2 percent / Et3N / CH2Cl2 / 0 - 20 °C 2.1: K2CO3 / dimethylsulfoxide / 1 h / 20 °C 2.2: 41.7 percent / dimethylsulfoxide / 72 h / 20 °C 3.1: 100 percent / bromine / acetic acid / 24 h / 20 °C 4.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C 4.2: 95.5 percent / tetrahydrofuran; hexane / -78 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: 80.2 percent / Et3N / CH2Cl2 / 0 - 20 °C 2.1: K2CO3 / dimethylsulfoxide / 1 h / 20 °C 2.2: 41.7 percent / dimethylsulfoxide / 72 h / 20 °C 3.1: 100 percent / bromine / acetic acid / 24 h / 20 °C 4.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C 4.2: 95.5 percent / tetrahydrofuran; hexane / -78 - 20 °C 5.1: 3.78 g / H2O2 / acetone; H2O / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: 80.2 percent / Et3N / CH2Cl2 / 0 - 20 °C 2.1: K2CO3 / dimethylsulfoxide / 1 h / 20 °C 2.2: 41.7 percent / dimethylsulfoxide / 72 h / 20 °C 3.1: 100 percent / bromine / acetic acid / 24 h / 20 °C 4.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C 4.2: 95.5 percent / tetrahydrofuran; hexane / -78 - 20 °C 5.1: 3.78 g / H2O2 / acetone; H2O / 0 °C 6.1: lithium diisopropylamide / tetrahydrofuran / 0.5 h / -78 °C 6.2: 1,2-diidoethane / tetrahydrofuran / -78 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1.1: 80.2 percent / Et3N / CH2Cl2 / 0 - 20 °C 2.1: K2CO3 / dimethylsulfoxide / 1 h / 20 °C 2.2: 41.7 percent / dimethylsulfoxide / 72 h / 20 °C 3.1: 100 percent / bromine / acetic acid / 24 h / 20 °C 4.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C 4.2: 95.5 percent / tetrahydrofuran; hexane / -78 - 20 °C 5.1: 3.78 g / H2O2 / acetone; H2O / 0 °C 6.1: lithium diisopropylamide / tetrahydrofuran / 0.5 h / -78 °C 6.2: 1,2-diidoethane / tetrahydrofuran / -78 - 20 °C 7.1: Cu powder / dimethylformamide / 12 h / 140 °C 8.1: 89.5 percent / trichlorosilane; tributylamine / toluene / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1.1: 80.2 percent / Et3N / CH2Cl2 / 0 - 20 °C 2.1: K2CO3 / dimethylsulfoxide / 1 h / 20 °C 2.2: 41.7 percent / dimethylsulfoxide / 72 h / 20 °C 3.1: 100 percent / bromine / acetic acid / 24 h / 20 °C 4.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C 4.2: 95.5 percent / tetrahydrofuran; hexane / -78 - 20 °C 5.1: 3.78 g / H2O2 / acetone; H2O / 0 °C 6.1: lithium diisopropylamide / tetrahydrofuran / 0.5 h / -78 °C 6.2: 1,2-diidoethane / tetrahydrofuran / -78 - 20 °C 7.1: Cu powder / dimethylformamide / 12 h / 140 °C 8.1: 92 percent / trichlorosilane; tributylamine / toluene / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: 80.2 percent / Et3N / CH2Cl2 / 0 - 20 °C 2.1: K2CO3 / dimethylsulfoxide / 1 h / 20 °C 2.2: 41.7 percent / dimethylsulfoxide / 72 h / 20 °C 3.1: 100 percent / bromine / acetic acid / 24 h / 20 °C 4.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C 4.2: 95.5 percent / tetrahydrofuran; hexane / -78 - 20 °C 5.1: 3.78 g / H2O2 / acetone; H2O / 0 °C 6.1: lithium diisopropylamide / tetrahydrofuran / 0.5 h / -78 °C 6.2: 1,2-diidoethane / tetrahydrofuran / -78 - 20 °C 7.1: Cu powder / dimethylformamide / 12 h / 140 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: 80.2 percent / Et3N / CH2Cl2 / 0 - 20 °C 2.1: K2CO3 / dimethylsulfoxide / 1 h / 20 °C 2.2: 41.7 percent / dimethylsulfoxide / 72 h / 20 °C 3.1: 100 percent / bromine / acetic acid / 24 h / 20 °C 4.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C 4.2: 95.5 percent / tetrahydrofuran; hexane / -78 - 20 °C 5.1: 3.78 g / H2O2 / acetone; H2O / 0 °C 6.1: lithium diisopropylamide / tetrahydrofuran / 0.5 h / -78 °C 6.2: 1,2-diidoethane / tetrahydrofuran / -78 - 20 °C 7.1: Cu powder / dimethylformamide / 12 h / 140 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 85 percent / diethyl azodicarboxylate; PPh3 / tetrahydrofuran / 20 °C 2: 75 percent / diethyl azodicarboxylate; PPh3 / tetrahydrofuran / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: 85 percent / diethyl azodicarboxylate; PPh3 / tetrahydrofuran / 20 °C 2.1: 75 percent / diethyl azodicarboxylate; PPh3 / tetrahydrofuran / 20 °C 3.1: nBuLi / tetrahydrofuran; hexane / 1 h / -78 °C 3.2: CuCN / tetrahydrofuran; hexane / 2 h / -78 °C 3.3: 50 percent / O2 / tetrahydrofuran; hexane / -78 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 95 percent / p-TsOH / toluene / Heating 2: 90 percent / BH3*THF / tetrahydrofuran / 96 h / Heating | ||
Multi-step reaction with 2 steps 1: 95 percent / toluenesulfonic acid / toluene 2: 90 percent / BH2Cl*SMe2 / diethyl ether / 12 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 13 steps 1: 1) NaH (60percent in oil) / 1) THF, 2 h, RT, 2) THF, 45 min 2: 84 percent / pyridine / 72 h / 4 °C 3: 85 percent / hexamethylphosphoric acid triamide / 0 deg C, 30 min; RT, 24 h 4: 1) DIBAL-H (0.93 M in hexane), 2) H2O, KHSO4 / 1) CH2Cl2, -78 deg C, 1.5 h, 2) CH2Cl2, 78 deg C to RT 5: CH2Cl2 / 72 h / Ambient temperature 6: 89 percent / DIBAL-H (1.5 M in hexane) / CH2Cl2 / 0.5 h / -78 °C 7: PPh3, I2, imidazole / acetonitrile; tetrahydrofuran / 0.17 h / -10 °C 8: 1) 1.0 M sodium hexamethyldisilazide in THF / 1)THF, -78 deg C, 1 h, 2) THF, -72 deg C, 24 h 9: 96 percent / LiOH, 30percent H2O2 / tetrahydrofuran / 1 h / 0 °C 10: 85 percent / DCC, DMAP / CH2Cl2 / 0 deg C, 1 h; RT, 24 h 11: 84 percent / TBAF / tetrahydrofuran / 16 h / Ambient temperature 12: 1) PPh3, DEAD, HCOOH, 2) MeOH, aq. NaHCO3 / 1) Et2O, 0 deg C 10 min then RT, 1 h 13: 95 percent / PPh3, DEAD / tetrahydrofuran / 0 deg C, 30 min; RT, 36 h | ||
Multi-step reaction with 12 steps 1: 1) NaH (60percent in oil) / 1) THF, 2 h, RT, 2) THF, 45 min 2: 84 percent / pyridine / 72 h / 4 °C 3: 85 percent / hexamethylphosphoric acid triamide / 0 deg C, 30 min; RT, 24 h 4: 1) DIBAL-H (0.93 M in hexane), 2) H2O, KHSO4 / 1) CH2Cl2, -78 deg C, 1.5 h, 2) CH2Cl2, 78 deg C to RT 5: CH2Cl2 / 72 h / Ambient temperature 6: 89 percent / DIBAL-H (1.5 M in hexane) / CH2Cl2 / 0.5 h / -78 °C 7: PPh3, I2, imidazole / acetonitrile; tetrahydrofuran / 0.17 h / -10 °C 8: 1) 1.0 M sodium hexamethyldisilazide in THF / 1)THF, -78 deg C, 1 h, 2) THF, -72 deg C, 24 h 9: 96 percent / LiOH, 30percent H2O2 / tetrahydrofuran / 1 h / 0 °C 10: 85 percent / DCC, DMAP / CH2Cl2 / 0 deg C, 1 h; RT, 24 h 11: 84 percent / TBAF / tetrahydrofuran / 16 h / Ambient temperature 12: 1) carbonyldiimidazole / 1) THF, 0 deg C, 15 min then RT, 2 h, 2) THF, RT, 30 h, 5 kbar | ||
Multi-step reaction with 10 steps 1: 95 percent / NaH / tetrahydrofuran / 2.75 h / Ambient temperature 2: 84 percent / pyridine / 72 h / 4 °C 3: 85 percent / hexamethylphosphoric acid triamide / 18 h / Ambient temperature 4: 1.) diisobutylaluminum hydride / 1.) CH2Cl2, -78 deg C, 1 h, 2.) CH2Cl2, rt., 93 h 5: 89 percent / diisobutylaluminum hydride / CH2Cl2 / 1.5 h / -78 °C 6: iodine, triphenylphosphine, imidazole / tetrahydrofuran; acetonitrile / 0.17 h / -10 °C 7: 2.) LiOH, 30 percent H2O2, H2O / 1.) THF, -72 deg C, 24 h, 2.) THF, 0 deg C, 1 h 8: 85 percent / DCC, DMAP / CH2Cl2 / 9 h / Ambient temperature 9: 84 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 16 h / Ambient temperature 10: 30 h / 3750300 Torr / Ambient temperature |
Multi-step reaction with 11 steps 1: 95 percent / NaH / tetrahydrofuran / 2.75 h / Ambient temperature 2: 84 percent / pyridine / 72 h / 4 °C 3: 85 percent / hexamethylphosphoric acid triamide / 18 h / Ambient temperature 4: 1.) diisobutylaluminum hydride / 1.) CH2Cl2, -78 deg C, 1 h, 2.) CH2Cl2, rt., 93 h 5: 89 percent / diisobutylaluminum hydride / CH2Cl2 / 1.5 h / -78 °C 6: iodine, triphenylphosphine, imidazole / tetrahydrofuran; acetonitrile / 0.17 h / -10 °C 7: 2.) LiOH, 30 percent H2O2, H2O / 1.) THF, -72 deg C, 24 h, 2.) THF, 0 deg C, 1 h 8: 85 percent / DCC, DMAP / CH2Cl2 / 9 h / Ambient temperature 9: 84 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 16 h / Ambient temperature 10: 86 percent / diethyl azodicarboxylate, triphenylphosphine, formic acid / diethyl ether / 1 h / Ambient temperature 11: 95 percent / diethyl azodicarboxylate, triphenylphosphine / tetrahydrofuran / 36 h / Ambient temperature; other tripeptide derivatives |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 49 percent / pyridine 2: 1.) Li / 1.) THF, 2.) THF, from -10 deg C to RT | ||
Multi-step reaction with 2 steps 1: pyridine / 0 °C / overnight 2: 1.) Li / 1.) THF, reflux, 3 h; 2.) THF, 0 deg C, then Rt, overnight |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: oxalic acid / tetrahydrofuran / Linde 4A molecular sieves 2: 82 percent / 1.) titanium tetrachloride, 2,4,6-trimethylpyridine, 2.) 1 M hydrochloric acid / CH2Cl2 / 1.) -78 degC, 5 min., 2.) -78 degC to r.t. 3: pyridinium chlorochromate / CH2Cl2 / 18 h / 25 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: oxalic acid / tetrahydrofuran / Linde 4A molecular sieves 2: 82 percent / 1.) titanium tetrachloride, 2,4,6-trimethylpyridine, 2.) 1 M hydrochloric acid / CH2Cl2 / 1.) -78 degC, 5 min., 2.) -78 degC to r.t. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: oxalic acid / tetrahydrofuran / Linde 4A molecular sieves 2: 9 percent / 1.) titanium tetrachloride, 2,4,6-trimethylpyridine, 2.) 1 M hydrochloric acid / CH2Cl2 / 1.) -78 degC, 5 min., 2.) -78 degC to r.t. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridinium p-toluenesulfonate; In toluene; | (d) A mixture of 15.6 g (0.105 mol) of <strong>[52698-46-1]1,1,1-trimethoxyisobutane</strong>, 10 g (0.0962 mol) of 2(S),4(S)-dihydroxypentane, and 251 mg of PPTS in 150 ml of toluene (dried over 3 A sieves) was allowed to reflux under argon for 11/2 hours while azeotroping water formed using the Dean-Stark trap. The reaction mixture was cooled, 1.2 g of potassium tert. butoxide was added, and the solvent was distilled. Ether (100 ml) was added to the residue, passed through a supercel pad eluding with 300 ml of ether, and the combined solvent was distilled in vacuo (<40 C.). The residue was distilled to afford 14.3 g (79.4%) of 2-isopropyl-2-methoxy-4(R),6(R)-dimethyl-1,3-dioxane, b.p. 78-82 C./15 mm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | for 0.333333h; Microwave irradiation; | 1 (2S,4S)-Pentane-2,4-diol (1 mmol), dioxane (1 mL), and fluorinating agent A (1 mmol) were placed in a Teflon (registered trademark) PFA container and sufficiently mixed. The mixture was placed in a microwave irradiator (product of Sharp, 2.45 GHz, 500 W) and irradiated with a microwave for 10 minutes. After cooling, fluorinating agent A (1 mmol) was further added to the mixture, and the resultant mixture was irradiated with a microwave for another 10 minutes. The reaction mixture was cooled to room temperature, and poured into a saturated aqueous sodium hydrogencarbonate solution. The system was subjected to extraction with ether (40 mL, three times). The ether solution was dried over magnesium sulfate, concentrated, and purified through silica gel column chromatography, whereby (2S,4R)-2-(3-methylbenzoyloxy)-4-fluoropentane, which is a target compound, was produced (yield: 78%, optical purity: 100%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | In dichloromethane at 20℃; for 19h; | 194.b (194b); To a CH2Cl2 (5 mL) solution of (2S,4S)-(+)-pentanediol (209 mg, 2 mmol) was added the salt (1.90 g, 3.1 eq) from reaction 194a at room temperature. The mixture was stirred for 19 h, filtered through a short bed of silica gel and concentrated to give the crude bis(O-trimethylsilyl)ether (0.40 g, 80%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87.5% | With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 35℃; for 1h; sonication; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
18% | With sodium hydride In tetrahydrofuran at 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With toluene-4-sulfonic acid In benzene Heating / reflux; | 1A; 1B To a solution of l-benzyl-3-methylpiperidin-4-one (Acros, 62.09 g, 305.4 mmol) and (2S,4S)- pentane-2,4-diol (TCI-US, 34.06 g, 327.0 mmol) in benzene (800 mL) was added p-toluenesulfonic acid mono hydrate (69.72 g, 404.9 mmol). The flask was fitted with a Dean-Stark trap and heated to reflux. The reaction mixture was cooled after 16 hours of reflux, concentrated to a total volume of about 500 mL and transferred to an Erlenmeyer flask with ethyl acetate. A sodium bicarbonate solution (500 mL) added with stirring and the mixture was further neutralized with solid Na2CO3 (35 g). The layers were partitioned, the organic phase washed with sodium bicarbonate, dried (Na2SO4) and concentrated to yield approximately 95 g of crude material. The residue was purified in 15 g batches by silica gel chromatography (Analogix SF-65-600 g; 35 micron silica; elution with 10% ethyl acetate-hexane) at 50 mL/min to provide 42.33 g of the first eluting isomer, (2S,4S,7R)-9- benzyl-2,4,7-trimethyl-l,5-dioxa-9-azaspiro[5.5]undecane. 1H NMR (300 MHz, DMSO-d6) δ 7.33- 7.19 (m, 5H), 4.07-3.86 (m, 2H), 3.40 (ABq, 2H, JAB = 13.5 Hz, 8VAB = 23.3 Hz), 2.41-2.20 (m, 4H), 1.90-1.76 (m, 2H), 1.59-1.47 (m, 3H), 1.12 (d, 3H, J = 6.4 Hz), 1.11 (d, 3H, J = 6.4 Hz), 0.90 (d, 3H, J = 7.1 Hz); MS (DCIZNH3) mZe 290 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With N-iodo-succinimide; trifluorormethanesulfonic acid In dichloromethane at 0℃; for 0.05h; Inert atmosphere; Molecular sieve; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
22% | With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0℃; Sonication; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran Inert atmosphere; | |
86% | With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃; | |
78.2% | With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0℃; for 4h; Sonication; |
78.2% | With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 35℃; Sonication; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | Stage #1: (2S,4S)-pentane-2,4-diol With n-butyllithium In tetrahydrofuran; hexane at -40 - 20℃; for 0.5h; Inert atmosphere; Stage #2: 1,1'-dicyano-3,3',4',4-tetramethyl-5,5'-diphenyl-2,2'-biphosphole In tetrahydrofuran; hexane at -40 - 20℃; for 16h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 52% 2: 15% | With 4-Phenyl-2-butanone; 2,4-dinitrobenzenesulfonic acid In benzene for 2h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
8% | With pyridinium p-toluenesulfonate In benzene for 34h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 56% 2: 50% 3: 12% | With 2,4-dinitrobenzenesulfonic acid In benzene for 2.5h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 61% 2: 55% 3: 15% | With 2,4-dinitrobenzenesulfonic acid In benzene for 2.5h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 62% 2: 61% 3: 24% | With 2,4-dinitrobenzenesulfonic acid In benzene for 3h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
44% | In toluene Reflux; Dean stark trap; | Intermediate 14: methyl(3S,7S,9S)-7,9-dimethyl-2-{A/-[(methyloxy)carbonyll-L-valyl)- 6,10-dioxa-2 azaspiro [4.51decane-3-carboxylateMethyl N-[(methyloxy)carbonyl]-L-valyl-4-oxo-L-prolinate (Intermediate 13) (650mg, 2.164mmol), (2S,4S)-2,4-pentanediol (902mg, 8.66mmol) and TsOH (82mg, 0.43mmol) were heated to reflux in toluene (40ml_) with Dean Stark trap overnight. After cooled down to rt and diluted with ethyl acetate, the resulting solution was washed with NaHC03 (ss) and brine. The organic later was dried over MgS04, filtered and evaporated. The crude product was purified by column chromatography (silica gel, 0 to 50% ethyl acetate in hexane) to give methyl (3S,7S,9S)-7,9-dimethyl- 2-{N-[(methyloxy)carbonyl]-L-valyl}-6,10-dioxa-2-azaspiro[4.5]decane-3-carboxylate (Intermediate 14) (366mg, yield: 44%) as an oil. 1H NMR (400 MHz,CHLOROFORM-c ) δ ppm 5.38 - 5.51 (m, 1 H) 4.54 (t, J=8.03 Hz, 1 H) 4.25 - 4.36 (m, 1 H) 3.91 - 4.05 (m, 2 H) 3.85 (d, J=10.04 Hz, 1 H) 3.54 - 3.77 (m, 6 H) 2.46 - 2.53 (m, 1 H) 2.12 (dd, J=12.92, 7.65 Hz, 1 H) 2.00 - 2.06 (m, 1 H) 1.54 - 1.75 (m, 3 H) 1.10 - 1.25 (m, 6 H) 1.03 (d, J=6.78 Hz, 3 H) 0.84 - 0.96 (m, 3 H). ES LC-MS m/z =409.3 (M+Na)+. |
With toluene-4-sulfonic acid Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
387 mg | With triethylamine In benzene at 0 - 95℃; for 1.25h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With toluene-4-sulfonic acid In chloroform-d1 for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With toluene-4-sulfonic acid In chloroform-d1 for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With toluene-4-sulfonic acid In chloroform-d1 for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With toluene-4-sulfonic acid In chloroform-d1 for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With toluene-4-sulfonic acid In chloroform-d1 for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With toluene-4-sulfonic acid In dichloromethane |
[ 13074-06-1 ]
(2R,3S,4R,5S)-Hexane-1,2,3,4,5-pentaol
Similarity: 0.92
[ 13074-06-1 ]
(2R,3S,4R,5S)-Hexane-1,2,3,4,5-pentaol
Similarity: 0.92