(1R,2R)-1,2-cyclohexanedicarboxylic acid dimethyl ester
(+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane
Conditions | Yield |
---|---|
With hydrogen In methanol at 190℃; under 52505.3 Torr; Temperature; Pressure; Solvent; | 94% |
Stage #1: (1R,2R)-1,2-cyclohexanedicarboxylic acid dimethyl ester With diisobutylaluminium hydride In toluene at -5 - 20℃; for 6h; Inert atmosphere; Stage #2: With hydrogenchloride; water In toluene at -5 - 40℃; for 13h; | 74% |
With lithium aluminium tetrahydride In diethyl ether | |
Stage #1: (1R,2R)-1,2-cyclohexanedicarboxylic acid dimethyl ester With diisobutylaluminium hydride In toluene at 0 - 20℃; for 4h; Inert atmosphere; Stage #2: With hydrogenchloride In water at 0 - 40℃; for 18h; | |
With methanol; sodium tetrahydroborate In tetrahydrofuran at 40℃; for 3h; Temperature; Reflux; |
(1R,2R)-(-)-trans-cyclohexane-1,2-dicarboxylic acid
(+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane
Conditions | Yield |
---|---|
With sodium tetrahydroborate; iodine In tetrahydrofuran at 0℃; for 5h; Reflux; | 88.4% |
With Red-Al In tetrahydrofuran; toluene for 5h; Inert atmosphere; Reflux; | 85.2% |
Multi-step reaction with 2 steps 1: diethyl ether 2: LiAlH4 / diethyl ether View Scheme |
(-)-(1R,2R)-trans-2-(hydroxymethyl)cyclohexanoic acid
(+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In diethyl ether for 12h; Heating; | 80% |
With lithium aluminium tetrahydride |
(+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In diethyl ether at 0 - 20℃; for 19h; Inert atmosphere; | 76% |
(+/-)-trans-2-(hydroxymethyl)cyclohexylmethanol
(+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane
Conditions | Yield |
---|---|
With C11H19NO |
(+/-)-trans-2-(hydroxymethyl)cyclohexylmethanol
A
trans-2-(hydroxymethyl)cyclohexanecarboxylic acid
B
(+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane
C
(1S,2S)-(–)-1,2-di(hydroxymethyl)cyclohexane
D
(-)-(1R,2R)-trans-2-(hydroxymethyl)cyclohexanoic acid
Conditions | Yield |
---|---|
With sodium hydroxide; NAD; silver nitrate; glycine; Flavin mononucleotide Product distribution; multistep reaction, other trans-diols, stereospecificity; |
diethyl trans-1,2,3,6-tetrahydrophthalate
(+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane
Conditions | Yield |
---|---|
Stage #1: diethyl trans-1,2,3,6-tetrahydrophthalate With hydrogen; palladium on activated charcoal Stage #2: With lithium aluminium tetrahydride |
(3aR,7aS)-1,3,3a,4,7,7a-hexahydroisobenzofuran-1-one
(+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 86 percent / H2 / Pd/C / methanol 2: 34 percent / NaOH / H2O / 192 h / 130 °C 3: 80 percent / LiAlH4 / diethyl ether / 12 h / Heating View Scheme |
cis-1,2-cyclohexanedimethanol
(+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 80 percent / NAD+, FMN, pH 9, HLADH, NaOH, glycine / Ambient temperature 2: 34 percent / NaOH / H2O / 192 h / 130 °C 3: 80 percent / LiAlH4 / diethyl ether / 12 h / Heating View Scheme |
cis-1,6-dihydroxymethyl-3-cyclohexene
(+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 83 percent / NAD+, FMN, pH 9, HLADH, NaOH, glycine / 48 h / 20 °C 2: 86 percent / H2 / Pd/C / methanol 3: 34 percent / NaOH / H2O / 192 h / 130 °C 4: 80 percent / LiAlH4 / diethyl ether / 12 h / Heating View Scheme |
(3aR,7aS)-hexahydroisobenzofuran-1-one
(+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 34 percent / NaOH / H2O / 192 h / 130 °C 2: 80 percent / LiAlH4 / diethyl ether / 12 h / Heating View Scheme |
1,2-cis-cyclohexanedicarboxylic anhydride
(+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: LiAlH4 2: 80 percent / NAD+, FMN, pH 9, HLADH, NaOH, glycine / Ambient temperature 3: 34 percent / NaOH / H2O / 192 h / 130 °C 4: 80 percent / LiAlH4 / diethyl ether / 12 h / Heating View Scheme |
phthalic acid dimethyl ester
(+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: Raney nickel; methanol / 50 - 60 °C / 73550.8 Torr / Hydrogenation.Behandeln des Reaktionsprodukts mit methanol. Natriummethylat 2: LiAlH4; diethyl ether 3: (1R)-menthyl isocyanate View Scheme |
dimethyl cyclohexane-trans-1,2-dicarboxylate
(+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: LiAlH4; diethyl ether 2: (1R)-menthyl isocyanate View Scheme |
(+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: hydrogenchloride / water 2.1: sulfuric acid / 18 h / 40 °C 3.1: diisobutylaluminium hydride / toluene / 6 h / -5 - 20 °C / Inert atmosphere 3.2: 13 h / -5 - 40 °C View Scheme |
trans-1,2-cyclohexanedicarboxylic acid
(+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: ethanol / 6.5 h / -70 - 20 °C / Resolution of racemate 2.1: hydrogenchloride / water 3.1: sulfuric acid / 18 h / 40 °C 4.1: diisobutylaluminium hydride / toluene / 6 h / -5 - 20 °C / Inert atmosphere 4.2: 13 h / -5 - 40 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: ethanol / 30 h / 35 - 75 °C 1.2: 1 h 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 65 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: (R)-1-phenyl-ethyl-amine / methanol; isopropyl alcohol / 30 - 40 °C 2.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 1 h / 25 - 30 °C 2.2: 1 h View Scheme | |
Multi-step reaction with 4 steps 1: (R)-1-phenyl-ethyl-amine / methanol; isopropyl alcohol / 30 - 40 °C 2: tetrahydrofuran / 1 h / 25 - 30 °C 3: tetrahydrofuran / 45 - 50 °C 4: sodium tetrahydroborate; water / tetrahydrofuran / 1 h View Scheme |
trans-cyclohex-4-ene-1,2-dicarboxylic acid
(+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: palladium; hydrogen / methanol / 30 - 35 °C 2.1: ethanol / 30 h / 35 - 75 °C 2.2: 1 h 3.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 65 °C View Scheme |
(+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: methanol / 0 - 35 °C / Inert atmosphere 1.2: Inert atmosphere 2.1: Red-Al / tetrahydrofuran; toluene / 5 h / Inert atmosphere; Reflux View Scheme | |
Multi-step reaction with 3 steps 1: (R)-1-phenyl-ethyl-amine / 5 °C 2: sulfuric acid / 4 h / Reflux 3: sodium tetrahydroborate; methanol / tetrahydrofuran / 3 h / 40 °C / Reflux View Scheme | |
Multi-step reaction with 3 steps 1.1: diisopropylamine / ethanol / 3 h / -72 - 20 °C 2.1: sulfuric acid / 20 h / 10 - 50 °C 3.1: diisobutylaluminium hydride / toluene / 4 h / 0 - 20 °C / Inert atmosphere 3.2: 18 h / 0 - 40 °C View Scheme |
(+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: sulfuric acid / 20 h / 10 - 50 °C 2.1: diisobutylaluminium hydride / toluene / 4 h / 0 - 20 °C / Inert atmosphere 2.2: 18 h / 0 - 40 °C View Scheme |
dimethyl cis-1,2-cyclohexanedicarboxylate
(+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: sodium methylate / methanol / 4 h / Inert atmosphere; Reflux 1.2: 4 h / 75 °C / Inert atmosphere 1.3: 0 - 5 °C / pH 2 / Inert atmosphere 2.1: Red-Al / tetrahydrofuran; toluene / 5 h / Inert atmosphere; Reflux View Scheme |
(+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: tetrahydrofuran / 45 - 50 °C 2: sodium tetrahydroborate; water / tetrahydrofuran / 1 h View Scheme |
(+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane
Conditions | Yield |
---|---|
With sodium tetrahydroborate; water In tetrahydrofuran for 1h; | 15.5 g |
(+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane
tert-butyldimethylsilyl chloride
((1R,2R)-2-(((tert-butyldimethylsilyl)oxy)methyl)cyclohexyl)methanol
Conditions | Yield |
---|---|
Stage #1: (+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane With n-butyllithium In tetrahydrofuran; cyclohexane at 0 - 20℃; for 3.25h; Inert atmosphere; Stage #2: tert-butyldimethylsilyl chloride In tetrahydrofuran; cyclohexane at 20℃; for 1h; Inert atmosphere; | 99% |
(+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane
8-oxabicyclo[4,3,0]nonane-7-one
Conditions | Yield |
---|---|
With (CH3)5C5*Ir(-OCH2C(C6H5)2NH-) In acetone at 20℃; for 36h; | 98% |
(+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane
p-methoxybenzyl chloride
Conditions | Yield |
---|---|
Stage #1: (+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane With sodium hydride In N,N-dimethyl-formamide; mineral oil at -20℃; for 0.5h; Inert atmosphere; Stage #2: p-methoxybenzyl chloride In N,N-dimethyl-formamide; mineral oil at 20℃; for 1h; Inert atmosphere; | A 97% B 2% |
(+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane
Conditions | Yield |
---|---|
Stage #1: (+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane With oxalyl dichloride; dimethyl sulfoxide In dichloromethane at -60℃; Inert atmosphere; Stage #2: With triethylamine In dichloromethane at -50 - 20℃; Inert atmosphere; | 94% |
(+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane
methanesulfonyl chloride
(1R,2R)-(-)-trans-cyclohexane-1,2-diylbis(methylene)dimethanesulfonate
Conditions | Yield |
---|---|
With triethylamine at 0 - 5℃; Industrial scale; | 92.6% |
With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere; | 92% |
With triethylamine In chloroform at 0 - 20℃; for 5h; | 90.8% |
(+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane
p-toluenesulfonyl chloride
(R)-trans-1,2-bis-(toluene-4-sulfonyloxymethyl)-cyclohexane
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at -10 - 0℃; for 3h; Concentration; | 92.5% |
Conditions | Yield |
---|---|
Stage #1: (+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane With sodium hydroxide In tetrahydrofuran Stage #2: C18H17N3O2S In tetrahydrofuran at 70℃; for 2h; Reagent/catalyst; Solvent; Temperature; | 74% |
Conditions | Yield |
---|---|
Stage #1: (+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane With sodium hydroxide In tetrahydrofuran Stage #2: C18H17N3O2S In tetrahydrofuran at -10℃; | 32% |
(+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane
Conditions | Yield |
---|---|
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In water; dimethyl sulfoxide at 23℃; for 2h; |
(+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: o-iodoxybenzoic acid / dimethylsulfoxide; H2O / 2 h / 23 °C 2: benzene / 16 h / Heating View Scheme |
(+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: o-iodoxybenzoic acid / dimethylsulfoxide; H2O / 2 h / 23 °C 2: benzene / 16 h / Heating 3: 94 percent / triethylamine / CH2Cl2 / 0 °C 4: 84 percent / sodium iodide / acetone / 14 h / Heating View Scheme |
(+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: o-iodoxybenzoic acid / dimethylsulfoxide; H2O / 2 h / 23 °C 2: benzene / 16 h / Heating 3: 94 percent / triethylamine / CH2Cl2 / 0 °C View Scheme |
(+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: o-iodoxybenzoic acid / dimethylsulfoxide; H2O / 2 h / 23 °C 2: benzene / 16 h / Heating 3: 94 percent / triethylamine / CH2Cl2 / 0 °C 4: 84 percent / sodium iodide / acetone / 14 h / Heating 5: 97 percent / ethanol / 120 h / Heating 6: 75 percent / potassium hydroxide; water / 8 h / Heating View Scheme |
(+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: o-iodoxybenzoic acid / dimethylsulfoxide; H2O / 2 h / 23 °C 2: benzene / 16 h / Heating 3: 94 percent / triethylamine / CH2Cl2 / 0 °C 4: 84 percent / sodium iodide / acetone / 14 h / Heating 5: 97 percent / ethanol / 120 h / Heating 6: 10 percent Chromat. / potassium hydroxide; water / 8 h / Heating View Scheme |
(+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: o-iodoxybenzoic acid / dimethylsulfoxide; H2O / 2 h / 23 °C 2: benzene / 16 h / Heating 3: 94 percent / triethylamine / CH2Cl2 / 0 °C 4: 84 percent / sodium iodide / acetone / 14 h / Heating 5: 70 percent / triethylamine / 120 h / Heating View Scheme |
(+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: o-iodoxybenzoic acid / dimethylsulfoxide; H2O / 2 h / 23 °C 2: benzene / 16 h / Heating 3: 94 percent / triethylamine / CH2Cl2 / 0 °C 4: 84 percent / sodium iodide / acetone / 14 h / Heating 5: 97 percent / ethanol / 120 h / Heating View Scheme |
(+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane
(3aR)-trans-octahydro-isobenzofuran
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: pyridine 2: aqueous KOH-solution View Scheme |
The (1R,2R)-1,2-Cyclohexanedimethanol, with the CAS registry number of 65376-05-8, is also known as (1R,2R)-1,2-Bis(hydroxymethyl)cyclohexane. The molecular formula of this chemical is C8H16O2 and its molecular weight is 144.21144. What's more, its systematic name is (1R,2R)-Cyclohexane-1,2-diyldimethanol.
Physical properties about (1R,2R)-1,2-Cyclohexanedimethanol are: (1)ACD/LogP: 0.53; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.53; (4)ACD/LogD (pH 7.4): 0.53; (5)ACD/BCF (pH 5.5): 1.48; (6)ACD/BCF (pH 7.4): 1.48; (7)ACD/KOC (pH 5.5): 46.15; (8)ACD/KOC (pH 7.4): 46.15; (9)#H bond acceptors: 2; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 18.46 Å2; (13)Index of Refraction: 1.47; (14)Molar Refractivity: 40.12 cm3; (15)Molar Volume: 143.5 cm3; (16)Polarizability: 15.9×10-24 cm3; (17)Surface Tension: 40.5 dyne/cm; (18)Density: 1.004 g/cm3; (19)Flash Point: 129 °C; (20)Enthalpy of Vaporization: 59.01 kJ/mol; (21)Boiling Point: 270.1 °C at 760 mmHg; (22)Vapour Pressure: 0.000923 mmHg at 25 °C.
You can still convert the following datas into molecular structure:
(1) SMILES: OC[C@@H]1CCCC[C@H]1CO
(2) InChI: InChI=1/C8H16O2/c9-5-7-3-1-2-4-8(7)6-10/h7-10H,1-6H2/t7-,8-/m0/s1
(3) InChIKey: XDODWINGEHBYRT-YUMQZZPRBI
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