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CAS No. : | 58520-04-0 | MDL No. : | MFCD08460191 |
Formula : | C16H20N2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 272.34 | Pubchem ID : | - |
Synonyms : |
|
Num. heavy atoms : | 20 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.25 |
Num. rotatable bonds : | 5 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 79.1 |
TPSA : | 70.5 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -7.01 cm/s |
Log Po/w (iLOGP) : | 2.33 |
Log Po/w (XLOGP3) : | 1.34 |
Log Po/w (WLOGP) : | 1.75 |
Log Po/w (MLOGP) : | 1.72 |
Log Po/w (SILICOS-IT) : | 2.23 |
Consensus Log Po/w : | 1.88 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.49 |
Solubility : | 0.888 mg/ml ; 0.00326 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.42 |
Solubility : | 1.03 mg/ml ; 0.00378 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.55 |
Solubility : | 0.00769 mg/ml ; 0.0000282 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 2.41 |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
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 |
---|---|---|
With magnesium sulfate In methanol at 50℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With triethylamine In dichloromethane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98 % ee | With dibenzoyltartaric acid In methanol Resolution of racemate; | 1.III.b b) Resolution of diamine 3b. Formation of a salt with ditoluoyltartaric acid in methanol and crystallisation from methanol initially gave (S1S) 4b in 74% ee. It should be possible to increase the ee by further crystallisation. Formation of a salt with dibenzoyltartaric acid in methanol and crystallisation from methanol initially gave 4b in98% ee. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | In triethylamine at 20℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With boron tribromide In dichloromethane for 48h; | |
With boron tribromide In dichloromethane at -78 - 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With boron tribromide In dichloromethane at 20℃; for 48h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With boron tribromide In dichloromethane for 48h; | ||
Multi-step reaction with 2 steps 1: 100 percent / BBr3 / CH2Cl2 / 48 h 2: 99 percent / polymer supported piperazine / methanol / 2 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: BBr3 / CH2Cl2 / -78 - 20 °C 2: 3.43 g / NaHCO3 / tetrahydrofuran; H2O / 20 °C | ||
Multi-step reaction with 2 steps 1: BBr3 / CH2Cl2 / 48 h 2: DIPEA / tetrahydrofuran / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: BBr3 / CH2Cl2 / -78 - 20 °C 2: 3.43 g / NaHCO3 / tetrahydrofuran; H2O / 20 °C 3: 64 percent / K2CO3; 18-crown-6 / dimethylformamide; tetrahydrofuran / 48 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: BBr3 / CH2Cl2 / -78 - 20 °C 2: 3.43 g / NaHCO3 / tetrahydrofuran; H2O / 20 °C 3: 64 percent / K2CO3; 18-crown-6 / dimethylformamide; tetrahydrofuran / 48 h / Heating 4: 100 percent / CH2Cl2 / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: BBr3 / CH2Cl2 / 48 h 2: DIPEA / tetrahydrofuran / 0 - 20 °C 3: 87 percent / K2CO3; 18-crown-6 / acetone / Heating 4: 96 percent / TFA / CH2Cl2 / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: BBr3 / CH2Cl2 / 48 h 2: DIPEA / tetrahydrofuran / 0 - 20 °C 3: 87 percent / K2CO3; 18-crown-6 / acetone / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: BBr3 / CH2Cl2 / 48 h 2: DIPEA / tetrahydrofuran / 0 - 20 °C 3: 78 percent / K2CO3; 18-crown-6 / acetone / Heating 4: 86 percent / TFA / CH2Cl2 / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: BBr3 / CH2Cl2 / 48 h 2: DIPEA / tetrahydrofuran / 0 - 20 °C 3: 78 percent / K2CO3; 18-crown-6 / acetone / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: BBr3 / CH2Cl2 / 48 h / 20 °C 2: 1.1 g / triethylamine / acetonitrile / 0.5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: BBr3 / CH2Cl2 / 48 h / 20 °C 2: 1.1 g / triethylamine / acetonitrile / 0.5 h / 20 °C 3: 89 percent / K2CO3 / dimethylformamide / 50 °C 4: 96 percent / trifluoroacetic acid / CH2Cl2 / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: BBr3 / CH2Cl2 / 48 h / 20 °C 2: 1.1 g / triethylamine / acetonitrile / 0.5 h / 20 °C 3: 89 percent / K2CO3 / dimethylformamide / 50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With triethylamine In dichloromethane at 0 - 20℃; for 1.5 - 26h; | 1.IV.b b) Tosyl-5b (Z = OCH3, B = 4-CH3-C6H4). Triethylamine (190 μl, 1.3 mmol) was added to a solution of the diamine 4b (175 mg, 0.65 mmol) in anhydrous dichloromethane (8 ml) and the solution was cooled to 00C. A solution of the tosyl chloride (p-toluenesulphonyl chloride, 1428 mg, 0.67 mmol) in anhydrous dichloromethane (5 ml) was added slowly. The mixture was stirred at 00C for 30-120 minutes and allowed to warm to room temperature over 1-24 hours. Water was added and the layers separated. The aqueous layer was extracted twice with dichloromethane and the combined organic layers were washed with brine, dried (Na2SO4) and evaporated. The crude mono-sulfonylated diamine could be purified by column chromatography. Purification by column chromatography gave 270 mg (91%) of Ts-5b as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ditoluoyltartaric acid; In methanol;Resolution of racemate;Purification / work up; | b) Resolution of diamine 3b. Formation of a salt with ditoluoyltartaric acid in methanol and crystallisation from methanol initially gave (S1S) 4b in 74% ee. It should be possible to increase the ee by further crystallisation. Formation of a salt with dibenzoyltartaric acid in methanol and crystallisation from methanol initially gave 4b in98% ee. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | In ethanol at 20℃; Reflux; optical yield given as %ee; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: ethanol / 20 °C 2: hydrogenchloride / water; tetrahydrofuran / 3 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride In tetrahydrofuran; water at 20℃; for 3h; | 3 EXAMPLE 3 EXAMPLE 3Hydrolysis of the diimine products formed by either Procedure A or B.[00107] The diimine products from either procedure A or B were dissolved in THF (30 mL) and aqueous HC1 (3 mL, 12 M) was added. The mixture stuffed at room temperature for 3 hours then was partitioned between H20 (100 mL) and CH2C12 (100 mL). The organic phase was removed and the aqueous phase washed with CH2C12 (100 mL). The aqueous phase was made basic by slow addition of 3 M NaOH. The resulting cloudy solution was extracted with CH2C12 (3 x 150 mL). The organic phases were dried over Na2SO4, filtered, and concentrated by rotovap. The resulting diamines are further dried by oil pump vacuum. | |
Stage #1: C30H28N2O4 With hydrogenchloride In tetrahydrofuran; water Stage #2: With sodium hydroxide In dichloromethane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With triethylamine In dichloromethane at 0 - 20℃; for 14h; | |
With triethylamine In dichloromethane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: cobalt(II) diacetate tetrahydrate; (1S,2S)-1,2-bis(4-methoxyphenyl)ethane-1,2-diamine With oxygen; pyrographite In methanol at 20℃; for 16h; Stage #2: hydrogenchloride In water |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: cobalt(II) perchlorate hexahydrate; (1S,2S)-1,2-bis(4-methoxyphenyl)ethane-1,2-diamine With pyrographite In methanol for 16h; Stage #2: hydrogenchloride In methanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
37% | Stage #1: Isophthalaldehyde; (1S,2S)-1,2-bis(4-methoxyphenyl)ethane-1,2-diamine In dichloromethane at 20℃; for 1.5h; Inert atmosphere; Stage #2: With N-Bromosuccinimide In dichloromethane at 0 - 20℃; for 24h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | Stage #1: benzaldehyde; (1S,2S)-1,2-bis(4-methoxyphenyl)ethane-1,2-diamine In dichloromethane at 20℃; for 1.33333h; Inert atmosphere; Stage #2: With N-Bromosuccinimide In dichloromethane at 0 - 20℃; for 17h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: toluene-4-sulfonic acid / para-xylene / 3 h / Reflux 2: water / 12 h / Reflux 3: hydrazine hydrate / ethanol / 6 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: toluene-4-sulfonic acid / para-xylene / 3 h / Reflux 2: water / 12 h / Reflux 3: hydrazine hydrate / ethanol / 6 h / Reflux 4: tetrahydrofuran / 24 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: phthalic anhydride; (1S,2S)-1,2-bis(4-methoxyphenyl)ethane-1,2-diamine With toluene-4-sulfonic acid In para-xylene for 3h; Reflux; Stage #2: With sodium hydrogencarbonate In dichloromethane; water |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid / para-xylene / 3 h / Reflux 2: water / 12 h / Reflux |
A635119[ 58520-03-9 ]
(1R,2R)-1,2-Di(4-methoxyphenyl)-1,2-diaminoethane
Reason: Optical isomers
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