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Chemistry
Organic Building Blocks
Aliphatic Cyclic Hydrocarbons
cyclohexyl
trans-N1,N2-Dimethylcyclohexane-1,2-diamine
Chemistry
Catalysts Ligands
Organic Building Blocks
Catalysis Chemistry Chiral nitrogen ligands
Aliphatic Cyclic Hydrocarbons
DACH or Trost Ligands
cyclohexyl

[ CAS No. 67579-81-1 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
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3d Animation Molecule Structure of 67579-81-1
Chemical Structure| 67579-81-1
Chemical Structure| 67579-81-1
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Quality Control of [ 67579-81-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 67579-81-1 ]

SDS Specification
Alternatived Products of [ 67579-81-1 ]

Product Details of [ 67579-81-1 ]

CAS No. :67579-81-1 MDL No. :MFCD03001702
Formula : C8H18N2 Boiling Point : -
Linear Structure Formula :- InChI Key :JRHPOFJADXHYBR-HTQZYQBOSA-N
M.W : 142.24 Pubchem ID :2733821
Synonyms :

Calculated chemistry of [ 67579-81-1 ]

Physicochemical Properties

Num. heavy atoms : 10
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 : 44.06
TPSA : 24.06 Ų

Pharmacokinetics

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) : -6.67 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.3
Log Po/w (XLOGP3) : 0.7
Log Po/w (WLOGP) : 0.74
Log Po/w (MLOGP) : 0.9
Log Po/w (SILICOS-IT) : 0.87
Consensus Log Po/w : 1.1

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.03
Solubility : 13.2 mg/ml ; 0.0931 mol/l
Class : Very soluble
Log S (Ali) : -0.78
Solubility : 23.5 mg/ml ; 0.165 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.94
Solubility : 1.64 mg/ml ; 0.0115 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.0

Safety of [ 67579-81-1 ]

Signal Word:Danger Class:8
Precautionary Statements:P280-P305+P351+P338-P310 UN#:3259
Hazard Statements:H302-H314 Packing Group:Ⅲ
GHS Pictogram:

Application In Synthesis of [ 67579-81-1 ]

* 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.

  • Downstream synthetic route of [ 67579-81-1 ]

[ 67579-81-1 ] Synthesis Path-Downstream   1~26

  • 1
  • [ 67579-81-1 ]
  • 2-chloro-1,3-dimethyl-octahydro-benzo[1,3,2]diazaphosphole [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N,N-diethylaniline; phosphorus trichloride In chloroform-d1
Reference： [1]Chauvin, Anne-Sophie; Bernardinelli, Gerald; Alexakis, Alexandre [Tetrahedron Asymmetry, 2006, vol. 17, # 15, p. 2203 - 2209]
  • 2
  • [ 67579-81-1 ]
  • 2-(indan-1-yloxy)-1,3-dimethyl-octahydro-benzo[1,3,2]diazaphosphole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N,N-diethylaniline; PCl3 / CDCl3 2: CDCl3
Reference： [1]Chauvin, Anne-Sophie; Bernardinelli, Gerald; Alexakis, Alexandre [Tetrahedron Asymmetry, 2006, vol. 17, # 15, p. 2203 - 2209]
  • 3
  • [ 67579-81-1 ]
  • 2-(2-isopropyl-5-methyl-cyclohexyloxy)-1,3-dimethyl-octahydro-benzo[1,3,2]diazaphosphole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N,N-diethylaniline; PCl3 / CDCl3 2: benzene; benzene-d6
Multi-step reaction with 2 steps 1: N,N-diethylaniline; PCl3 / CDCl3 2: CDCl3
Reference： [1]Chauvin, Anne-Sophie; Bernardinelli, Gerald; Alexakis, Alexandre [Tetrahedron Asymmetry, 2006, vol. 17, # 15, p. 2203 - 2209]
[2]Chauvin, Anne-Sophie; Bernardinelli, Gerald; Alexakis, Alexandre [Tetrahedron Asymmetry, 2006, vol. 17, # 15, p. 2203 - 2209]
  • 4
  • [ 67579-81-1 ]
  • 6-(1,3-dimethyl-octahydro-benzo[1,3,2]diazaphosphol-2-yloxy)-8-methyl-8-aza-bicyclo[3.2.1]octan-3-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N,N-diethylaniline; PCl3 / CDCl3
Reference： [1]Chauvin, Anne-Sophie; Bernardinelli, Gerald; Alexakis, Alexandre [Tetrahedron Asymmetry, 2006, vol. 17, # 15, p. 2203 - 2209]
  • 5
  • [ 67579-81-1 ]
  • 2-(indan-1-yloxy)-1,3-dimethyl-octahydro-benzo[1,3,2]diazaphosphole 2-sulfide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N,N-diethylaniline; PCl3 / CDCl3 2: CDCl3 3: sulfur / CDCl3
Reference： [1]Chauvin, Anne-Sophie; Bernardinelli, Gerald; Alexakis, Alexandre [Tetrahedron Asymmetry, 2006, vol. 17, # 15, p. 2203 - 2209]
  • 6
  • [ 67579-81-1 ]
  • 2-(2-isopropyl-5-methyl-cyclohexyloxy)-1,3-dimethyl-octahydro-benzo[1,3,2]diazaphosphole 2-sulfide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N,N-diethylaniline; PCl3 / CDCl3 2: benzene; benzene-d6 3: sulfur / CDCl3
Multi-step reaction with 3 steps 1: N,N-diethylaniline; PCl3 / CDCl3 2: CDCl3 3: sulfur / CDCl3
Reference： [1]Chauvin, Anne-Sophie; Bernardinelli, Gerald; Alexakis, Alexandre [Tetrahedron Asymmetry, 2006, vol. 17, # 15, p. 2203 - 2209]
[2]Chauvin, Anne-Sophie; Bernardinelli, Gerald; Alexakis, Alexandre [Tetrahedron Asymmetry, 2006, vol. 17, # 15, p. 2203 - 2209]
  • 7
  • [ 67579-81-1 ]
  • 1,3-dimethyl-2-(2-phenyl-cyclohexyloxy)-octahydro-benzo[1,3,2]diazaphosphole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N,N-diethylaniline; PCl3 / CDCl3 2: CDCl3
Reference： [1]Chauvin, Anne-Sophie; Bernardinelli, Gerald; Alexakis, Alexandre [Tetrahedron Asymmetry, 2006, vol. 17, # 15, p. 2203 - 2209]
  • 8
  • [ 67579-81-1 ]
  • 6-(1,3-dimethyl-2-thioxo-octahydro-2λ5-benzo[1,3,2]diazaphosphol-2-yloxy)-8-methyl-8-aza-bicyclo[3.2.1]octan-3-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N,N-diethylaniline; PCl3 / CDCl3 2: sulfur
Reference： [1]Chauvin, Anne-Sophie; Bernardinelli, Gerald; Alexakis, Alexandre [Tetrahedron Asymmetry, 2006, vol. 17, # 15, p. 2203 - 2209]
  • 9
  • [ 67579-81-1 ]
  • 2-(bicyclo[2.2.1]hept-2-yloxy)-1,3-dimethyl-octahydro-benzo[1,3,2]diazaphosphole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N,N-diethylaniline; PCl3 / CDCl3
Reference： [1]Chauvin, Anne-Sophie; Bernardinelli, Gerald; Alexakis, Alexandre [Tetrahedron Asymmetry, 2006, vol. 17, # 15, p. 2203 - 2209]
  • 10
  • [ 67579-81-1 ]
  • 1,3-dimethyl-2-(2-phenyl-cyclohexyloxy)-octahydro-benzo[1,3,2]diazophosphole 2-sulfide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N,N-diethylaniline; PCl3 / CDCl3 2: CDCl3 3: sulfur / CDCl3
Reference： [1]Chauvin, Anne-Sophie; Bernardinelli, Gerald; Alexakis, Alexandre [Tetrahedron Asymmetry, 2006, vol. 17, # 15, p. 2203 - 2209]
  • 11
  • [ 67579-81-1 ]
  • 2-(bicyclo[2.2.1]hept-2-yloxy)-1,3-dimethyl-octahydro-benzo[1,3,2]diazaphosphole 2-sulfide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N,N-diethylaniline; PCl3 / CDCl3 2: sulfur
Reference： [1]Chauvin, Anne-Sophie; Bernardinelli, Gerald; Alexakis, Alexandre [Tetrahedron Asymmetry, 2006, vol. 17, # 15, p. 2203 - 2209]
  • 12
  • [ 67579-81-1 ]
  • 1,3-dimethyl-2-(2-naphthalen-2-yl-cyclohexyloxy)-octahydro-benzo[1,3,2]diazaphosphole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N,N-diethylaniline; PCl3 / CDCl3 2: CDCl3
Reference： [1]Chauvin, Anne-Sophie; Bernardinelli, Gerald; Alexakis, Alexandre [Tetrahedron Asymmetry, 2006, vol. 17, # 15, p. 2203 - 2209]
  • 13
  • [ 67579-81-1 ]
  • 1,3-dimethyl-2-(2-naphthalen-2-yl-cyclohexyloxy)-octahydro-benzo[1,3,2]diazaphosphole 2-sulfide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N,N-diethylaniline; PCl3 / CDCl3 2: CDCl3 3: sulfur / CDCl3
Reference： [1]Chauvin, Anne-Sophie; Bernardinelli, Gerald; Alexakis, Alexandre [Tetrahedron Asymmetry, 2006, vol. 17, # 15, p. 2203 - 2209]
  • 14
  • [ 67579-81-1 ]
  • 17-(1,3-dimethyl-octahydro-benzo[1,3,2]diazaphosphol-2-yloxy)-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[<i>a</i>]phenanthren-3-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N,N-diethylaniline; PCl3 / CDCl3
Reference： [1]Chauvin, Anne-Sophie; Bernardinelli, Gerald; Alexakis, Alexandre [Tetrahedron Asymmetry, 2006, vol. 17, # 15, p. 2203 - 2209]
  • 15
  • [ 67579-81-1 ]
  • 17-(1,3-dimethyl-octahydro-benzo[1,3,2]diazaphosphol-2-yloxy)-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[<i>a</i>]phenanthren-3-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N,N-diethylaniline; PCl3 / CDCl3
Reference： [1]Chauvin, Anne-Sophie; Bernardinelli, Gerald; Alexakis, Alexandre [Tetrahedron Asymmetry, 2006, vol. 17, # 15, p. 2203 - 2209]
  • 16
  • [ 67579-81-1 ]
  • 3-(1,3-dimethyl-octahydro-benzo[1,3,2]diazaphosphol-2-yloxy)-10,13-dimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,16-tetradecahydro-cyclopenta[<i>a</i>]phenanthren-17-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N,N-diethylaniline; PCl3 / CDCl3
Reference： [1]Chauvin, Anne-Sophie; Bernardinelli, Gerald; Alexakis, Alexandre [Tetrahedron Asymmetry, 2006, vol. 17, # 15, p. 2203 - 2209]
  • 17
  • [ 67579-81-1 ]
  • 3-(1,3-dimethyl-octahydro-benzo[1,3,2]diazaphosphol-2-yloxy)-10,13-dimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,16-tetradecahydro-cyclopenta[<i>a</i>]phenanthren-17-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N,N-diethylaniline; PCl3 / CDCl3
Reference： [1]Chauvin, Anne-Sophie; Bernardinelli, Gerald; Alexakis, Alexandre [Tetrahedron Asymmetry, 2006, vol. 17, # 15, p. 2203 - 2209]
  • 18
  • [ 67579-81-1 ]
  • 1,3-dimethyl-2-[5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyloxy]-octahydro-benzo[1,3,2]diazaphosphole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N,N-diethylaniline; PCl3 / CDCl3 2: CDCl3
Reference： [1]Chauvin, Anne-Sophie; Bernardinelli, Gerald; Alexakis, Alexandre [Tetrahedron Asymmetry, 2006, vol. 17, # 15, p. 2203 - 2209]
  • 19
  • [ 67579-81-1 ]
  • 1,3-dimethyl-2-[5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyloxy]-octahydro-benzo[1,3,2]diazaphosphole 2-sulfide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N,N-diethylaniline; PCl3 / CDCl3 2: CDCl3 3: sulfur / CDCl3
Reference： [1]Chauvin, Anne-Sophie; Bernardinelli, Gerald; Alexakis, Alexandre [Tetrahedron Asymmetry, 2006, vol. 17, # 15, p. 2203 - 2209]
  • 20
  • [ 67579-81-1 ]
  • [ 137944-04-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N,N-diethylaniline; PCl3 / CDCl3 2: CDCl3
Reference： [1]Chauvin, Anne-Sophie; Bernardinelli, Gerald; Alexakis, Alexandre [Tetrahedron Asymmetry, 2006, vol. 17, # 15, p. 2203 - 2209]
  • 21
  • [ 67579-81-1 ]
  • [ 138125-60-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N,N-diethylaniline; PCl3 / CDCl3 2: CDCl3 3: sulfur / benzene; benzene-d6
Reference： [1]Chauvin, Anne-Sophie; Bernardinelli, Gerald; Alexakis, Alexandre [Tetrahedron Asymmetry, 2006, vol. 17, # 15, p. 2203 - 2209]
  • 22
  • [ 1415390-39-4 ]
  • [ 67579-81-1 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
In benzene diamine (1.1 mmol) added to soln. of diphenylphosphinoferrocenecarboxaldehyde (1 mmol) in degassed C6H6; stirred (75°C, 12 h); concd. (vac.); chromd. (SiO2 treated with Et3N, 5% EtOAc-hexane);
Reference： [1]Jin, Myung-Jong; Takale, Vijay B.; Sarkar; Kim, Young-Mok [Chemical Communications, 2006, vol. 6, # 6, p. 663 - 664]
  • 23
  • [ 67579-81-1 ]
  • [ 1079-66-9 ]
  • trans-1,2-(N,N'-bisdiphenylphosphino-N,N'-dimethylamino)cyclohexane [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With triethylamine In tetrahydrofuran at 20℃; 2 From this point all operations were carried out in a nitrogen atmosphere using standard Schlenk technique.Diphenylchlorophosphine (2.61 mL, 3.10 g, 14.06 mmol) was added to a stirred solution of triethylamine (3.0 mL, 2.18 g, 21.5 mmol) and trans-1,2-N,N'-dimethylaminocyclohexane (1.0 g, 7.03 mmol) in dry THF (20 mL). The resulting slurry was stirred overnight at ambient temperature and filtered. The filtered solid was washed with dry THF (2×10 mL). The combined filtrate was evaporated under vacuum to ca 5 mL and diluted with dry hexane (20 mL). The formed solid was filtered, washed with dry hexane (2×10 mL) and dried in vacuum to afford trans-1,2-(N,N'-bisdiphenylphosphino-N,N'-dimethylamino)cyclohexane as a snow-white solid. The yield was 2.65 g (74%). 31P{1H} NMR (C6D6, 25° C.), δ: 61.7 (s). The compound was stored under air.
Reference： [1]Current Patent Assignee: LANNETT CO INC - US7399859, 2008, B1 Location in patent: Page/Page column 7
  • 24
  • trans-1,2-bis(ethoxycarbonylamino)cyclohexane [ No CAS ]
  • [ 67579-81-1 ]
YieldReaction ConditionsOperation in experiment
88% Stage #1: trans-1,2-bis(ethoxycarbonylamino)cyclohexane With lithium aluminium tetrahydride In tetrahydrofuran at 5 - 20℃; Heating / reflux; Stage #2: With sodium hydroxide; water In tetrahydrofuran at 20℃; for 1h; Heating / reflux; 2 trans-1,2-bis(ethoxycarbonylamino)cyclohexane (22.0 g, 85.17 mmol) was added as a solid to a stirred mixture of dry THF (200 mL) and lithium aluminium hydride (12.0 g) cooled to 5° C. The resulting slurry was stirred under nitrogen at ambient temperature for 2 hours then heated to reflux overnight. The reaction mixture was cooled to 5° C. and treated carefully with water (24 mL) and then with 15% NaOH (18 mL). The resulting slurry was stirred at ambient temperature for 30 min, heated to reflux for 30 min and filtered while hot. The filtered solid was washed with THF (2×80 mL) and the combined filtrate was evaporated in vacuum. The residue was dissolved in pentane (100 mL), filtered through a short silica column and eluted with pentane (2×40 mL). The combined filtrate was evaporated in vacuum to give 10.3 g (88% yield) of trans-1,2-N,N'-dimethylaminocyclohexane as a colorless oil.
Reference： [1]Current Patent Assignee: LANNETT CO INC - US7399859, 2008, B1 Location in patent: Page/Page column 7-8
  • 25
  • [ 67579-81-1 ]
  • [ 1383705-71-2 ]
  • 1-(4-bromo-phenyl)-2,2,2-trifluoro-ethanol [ No CAS ]
  • [ 1383703-73-8 ]
YieldReaction ConditionsOperation in experiment
26% With sodium azide; D-(-)-isoascorbic acid sodium salt In water; dimethyl sulfoxide at 70℃; for 48h; Sealed vial; 150 Example 150 : 2,2,2-trifluoro-1 -f4-r4-(1 H-indazol-3-yl)-1 H-1 ,2,3-triazol-1 - yllphenvDethanol A mixture of 1-(4-bromophenyl)-2,2,2-trifluoroethan-1-ol (296 mg; 1.16 mmol; 1.1 eq.), 3- EthynyM H-indazole (150 mg; 1.06 mmol; 1.0 eq.), sodium azide (75 mg; 1.16 mmol; 1.1 eq.), D-(-)-isoascorbic acid sodium salt (21 mg; 0.11 mmol; 0.1 eq.), copper iodide (20 mg; 0.1 1 mmol; 0.1 eq.) and trans-1 ,2-bis(methylamino)cyclohexane (22 mg; 0.16 mmol; 0.15 eq.) in DMSO (2.6 ml_) and WATER (0.5 ml_) was heated in a sealed tube at 70°C for 48h. The reaction mixture was poured into a solution of saturated NH4OH and extracted with DCM (twice). Combined organic phases were washed with brine, dried over magnesium sulfate, filtered and concentrated. Purification by preparative HPLC gave the title compound as a beige solid (100 mg, 26%). 1 H NMR (DMSO) δ 13.38 (brs, 1 H), 9.33 (s, 1 H), 8.36 (dt, J= 8.0 Hz, 1.0 Hz, 1 H), 8.12 (d, J= 8.7 Hz, 2H), 7.75 (d, J= 8.7 Hz, 2H), 7.61 (dt, J= 8.4 Hz, 1.0 Hz, 1 H), 7.47-7.42 (m, 1 H), 7.29-7.23 (m, 1 H), 7.05 (bs, 1 H), 5.34 (q, J= 7.2 Hz, 1 H). HPLC (max plot) 100.0%; Rt %3.83min. UPLC/MS: (MS+) 360.4, (MS-) 358.4.
Reference： [1]Current Patent Assignee: MERCK KGAA - WO2012/84704, 2012, A1 Location in patent: Page/Page column 215-216
  • 26
  • [ 67579-81-1 ]
  • [ 727-62-8 ]
  • (±)-2-(((3aR,7aR)-1,3-dimethyloctahydro-2H-benzo[d]imidazol-2-ylidene)amino)-N-phenylbenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With triethylamine In acetonitrile at 150℃; for 2h; Microwave irradiation;
Reference： [1]Yan, Gang; Zekarias, Bereket L.; Li, Xiaoyu; Jaffett, Victor A.; Guzei, Ilia A.; Golden, Jennifer E. [Chemistry - A European Journal, 2020, vol. 26, # 11, p. 2486 - 2492]

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