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Chemical Structure| 21436-03-3 Chemical Structure| 21436-03-3

Structure of (S,S)-DACH
CAS No.: 21436-03-3

Chemical Structure| 21436-03-3

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Synonyms: (1S,2S)-(+)-1,2-Diaminocyclohexane

4.5 *For Research Use Only !

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Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

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Product Citations

Product Citations

Root, Harrison D ; Hurlock, Matthew J ; Bays, Nathan R ; Addison, Brianna M ; Rimsza, Jessica M ;

Abstract: The demand for low-cost, low-energy, and highly selective gas capture and separations is an ongoing driver of porous material development. Porous liquids have been identified as a promising gas separation material by creating permanent porosity in inorganic solvents through inclusion of nanoporous materials that sterically exclude solvent from their internal porosity. Among the nanoporous materials that can be used to form porous liquids, porous-organic cages (POCs) have been one of the most popular due to the inherent tunability of POCs. “Scrambled” POCs with varying functionalities on the POC vertices have been developed and incorporated into porous liquid compositions, increasing their gas adsorption capacity. An unexplored avenue to tailor the properties of porous liquids is through scrambling the functionality of the core of the POC. Therefore, we have synthesized a new POC, a CC3-OH derivative with scrambled hydroxides on the core and evaluated the impact on the CO2 uptake capacity in silicon oil-based porous liquids. Core scrambling of the POC resulted in a twofold increase CO2 adsorption capacity in the porous liquid, an emergent property that is a dramatic increase beyond a linear combination of the gas adsorption capacity of the neat solvent and the POC. Density functional theory modeling of the CC3 POC and its hydroxide-based derivatives identified that free rotation of the linker hydroxide allowed for forced interaction between the CO2 molecule and the hydroxide in the pore window. Solvation of the POC may release scrambled core hydroxides from intramolecular bonding with a neighboring imine, allowing for increased gas uptake in the porous liquid over the neat POC. These results identify a key structural relationship of POCs that enables emergent properties in porous liquids and can guide future development of liquid phase gas capture and separation materials for environmental and industrial applications.

Keywords: Porous liquids ; Gas capture ; Gas separation ; Porous organic cages

Purchased from AmBeed: ; ;

Alternative Products

Product Details of [ 21436-03-3 ]

CAS No. :21436-03-3
Formula : C6H14N2
M.W : 114.19
SMILES Code : N[C@@H]1[C@@H](N)CCCC1
Synonyms :
(1S,2S)-(+)-1,2-Diaminocyclohexane
MDL No. :MFCD00062986
InChI Key :SSJXIUAHEKJCMH-WDSKDSINSA-N
Pubchem ID :479307

Safety of [ 21436-03-3 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H227-H303-H314-H335
Precautionary Statements:P210-P261-P264-P271-P280-P301+P330+P331-P303+P361+P353-P304+P340+P310-P305+P351+P338+P310-P312-P363-P370+P378-P403+P233-P403+P235-P405-P501
Class:8
UN#:2735
Packing Group:

Computational Chemistry of [ 21436-03-3 ] Show Less

Physicochemical Properties

Num. heavy atoms 8
Num. arom. heavy atoms 0
Fraction Csp3 1.0
Num. rotatable bonds 0
Num. H-bond acceptors 2.0
Num. H-bond donors 2.0
Molar Refractivity 34.26
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

52.04 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

1.37
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

-0.32
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

0.21
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

0.21
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

0.15
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.33

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-0.35
Solubility 51.4 mg/ml ; 0.45 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-0.31
Solubility 55.7 mg/ml ; 0.488 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-0.31
Solubility 55.8 mg/ml ; 0.489 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

No
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-7.22 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

1.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

0.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

1.81

Application In Synthesis of [ 21436-03-3 ]

* 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 [ 21436-03-3 ]

[ 21436-03-3 ] Synthesis Path-Downstream   1~17

  • 1
  • [ 24424-99-5 ]
  • [ 21436-03-3 ]
  • [ 180683-64-1 ]
YieldReaction ConditionsOperation in experiment
34% With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 24h;Inert atmosphere; General procedure: A mixture of piperazine (500mg, 5.8mmol, 1.0eq.), N,N-diisopropylethylamine (DIPEA) (1.5mL, 8.7mmol, 1.5eq.), and di-tert-butyl dicarbonate (Boc2O) (500mg, 2.3mmol, 0.4eq.) in dry dichloromethane (15mL) was stirred at room temperature for 24h under nitrogen atmosphere. The reaction mixture was diluted with dichloromethane and washed with saturated aqueous NaHCO3 and brine. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The titled compound (4a) as a colorless solid was afforded after purification by column chromatography on silica gel (chloroform/methanol=50/1). The same procedure was performed to obtain compounds 4b and 4c
  • 2
  • [ 7089-68-1 ]
  • [ 21436-03-3 ]
  • SS-N,N'-bis(phenanthrolin-2-yl)-1,2-cyclohexanediamine [ No CAS ]
  • 3
  • [ 21436-03-3 ]
  • [ 34595-26-1 ]
  • (1S,2S)-N1,N2-bis(2-(piperidin-1-yl)benzylidene)cyclohexane-1,2-diamine [ No CAS ]
  • 4
  • [ 21436-03-3 ]
  • [ 7310-97-6 ]
  • (2S,3S,12S,13S,22S,23S)-1,4,11,14,21,24-hexaaza-(2,3:12,13:22,23)-tributano-7,8',17,18',27,28'-hexamethoxy-(6,9:16,19:26,29)-trietheno-2H,3H,12H,13H,22H,23H-hexahydro-(30)-annulene [ No CAS ]
  • 5
  • [ 37942-07-7 ]
  • [ 21436-03-3 ]
  • [ 135616-40-9 ]
  • 6
  • [ 21436-03-3 ]
  • [ 21286-54-4 ]
  • [ 609810-67-5 ]
  • 7
  • [ 21436-03-3 ]
  • [ 180683-64-1 ]
YieldReaction ConditionsOperation in experiment
[Referential Example 39] (+-)-trans-N-tert-Butoxycarbonyl-1,2-cyclohexanediamine: The title compound was obtained from (+-)-trans-1,2-cyclohexanediamine in a similar manner to Referential Example 34. mp 79-81C. 1H-NMR (CDCl3) delta: 1.05-1.34(4H,m), 1.45(9H,s), 1.68-1.75(2H,m), 1.92-2.02(2H,m), 2.32(1H,dt,J=10.3,3.9Hz), 3.08-3.20(1H,m), 4.50(1H,br.s). MS (FAB) m/z: 215(M+H)+.
  • 8
  • [ 58632-95-4 ]
  • [ 21436-03-3 ]
  • [ 180683-64-1 ]
  • 9
  • [ 3328-69-6 ]
  • [ 21436-03-3 ]
  • C42H48N6O3 [ No CAS ]
  • 10
  • [ 21436-03-3 ]
  • [ 147702-14-5 ]
  • (2R)-(+)-3,3'-diphenyl-[2,2'-dinaphthalene]-1,1'-diol [ No CAS ]
  • C32H22O2*C6H14N2 [ No CAS ]
  • (2S)-(-)-3,3'-diphenyl-(2,2'-binaphthalene)-1,1'-diol [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% In benzene;Reflux; Resolution of racemate; 1S,2S)-(+)-Diaminocyclohexane 2 (0.68g, 6mmol) was added to a solution of rac-<strong>[147702-14-5]VANOL</strong> 1 (4.38g, 10mmol) in benzene (30mL), and the resulting mixture was heated at reflux for 24h. The mixture was then cooled to room temperature and the resulting colorless crystals were isolated from the solution by filtration and washed with toluene (3×5mL). The process of refluxing and crystallizing was repeated twice, and the resulting crystals were combined, dried, and quantified, with 2.43g (88% yield) of the desired material being isolated; mp 204.1-211.5C; 1H NMR (CDCl3): δ 8.37 (m, 2H), 7.78 (m, 2H), 7.56 (m, 4H), 7.36 (s, 4H), 7.31 (s, 2H), 7.07 (t, 2H), 6.96 (t, 4H), 1.80 (m, 2H), 1.66 (m, 2H), 1.25 (m, 2H), 1.05 (m, 2H). 13C NMR (CDCl3): δ 151.0, 140.9, 140.4, 134.4, 128.9, 127.6, 127.3, 126.4, 125.4, 122.9, 121.5, 57.3, 35.2, 25.3. FTIR (KBr, cm-1): 3590, 3435, 3010, 2925, 2855, 1560, 1400, 1140.
  • 11
  • [ 21436-03-3 ]
  • [ 147702-14-5 ]
  • (2R)-(+)-3,3'-diphenyl-[2,2'-dinaphthalene]-1,1'-diol [ No CAS ]
  • C32H22O2*C6H14N2 [ No CAS ]
  • C32H22O2*C6H14N2 [ No CAS ]
  • (2S)-(-)-3,3'-diphenyl-(2,2'-binaphthalene)-1,1'-diol [ No CAS ]
  • 12
  • [ 24424-99-5 ]
  • [ 21436-03-3 ]
  • bis-BOC-(S, S)-cyclohexane diamine [ No CAS ]
  • [ 180683-64-1 ]
YieldReaction ConditionsOperation in experiment
In dichloromethane; at 20℃; for 12h;Inert atmosphere; To an ice cold solutionof (1S, 2S)-diaminocylohexane (570 mg, 5 mmol) in 3 ml ofdichloromethane was added a solution of di-t-butyldicarbonate (362.29 mg, 1.66 mmol) in dichloromethane over a period of 30 min. After complete addition of BOC anhydride, the reaction was allowed to stir for 12h at room temperature. The resultant precipitate was dissolved in 12 ml of water/ dichloromethane (1:1), after separation of two phases, the dichloromethane phase was concentrated under reduced pressure and the residue was dissolved in 12 ml of ether/water (1:1). The mixture was acidified to pH 5 using 4M hydrochloric acid solutions, and the bis-protected diamine was extracted with ether (3 X 50 ml). The combined ether extracts were washed thoroughly with water (2 X 100 ml) to take care of possible monoprotected diamine. Theether layer was then dried over anhydrous sodium sulphate and was concentrated under reduced pressure to yield bisprotected diamine. The aqueous phase was adjusted to pH 10 using 2M sodium hydroxide solution and was extracted with ethyl acetate (3 X 100 ml) and the combined organic extracts were driedover anhydrous sodium sulphate, then concentrated under reduced pressure to yield monoprotected diamine.
  • 13
  • [ 34619-03-9 ]
  • [ 21436-03-3 ]
  • [ 180683-64-1 ]
  • 14
  • [ 34374-88-4 ]
  • [ 21436-03-3 ]
  • C36H42N6O6 [ No CAS ]
  • 15
  • [ 51300-90-4 ]
  • [ 21436-03-3 ]
  • [ 180683-64-1 ]
  • 16
  • [ 180683-64-1 ]
  • [ 21436-03-3 ]
  • 17
  • [ 32608-29-0 ]
  • [ 21436-03-3 ]
  • (1S,2S)-N1,N2-bis(4-chloro-8-methoxyquinolin-2-yl)cyclohexane-1,2-diamine [ No CAS ]
 

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