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Structure of (S,S)-DACH
CAS No.: 21436-03-3
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
Synonyms: (1S,2S)-(+)-1,2-Diaminocyclohexane
4.5
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Unlocking enhanced gas capture via core scrambling of porous-organic cages
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.
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Keywords: Porous liquids ; Gas capture ; Gas separation ; Porous organic cages
Show More >
| 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 |
| 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: | Ⅲ |
| 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 |
52.04 Ų |
| Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.37 |
| Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
-0.32 |
| Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
0.21 |
| Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.21 |
| Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
0.15 |
| Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.33 |
| Log S (ESOL):? ESOL: Topological method implemented from |
-0.35 |
| Solubility | 51.4 mg/ml ; 0.45 mol/l |
| Class? Solubility class: Log S scale |
Very soluble |
| Log S (Ali)? Ali: Topological method implemented from |
-0.31 |
| Solubility | 55.7 mg/ml ; 0.488 mol/l |
| Class? Solubility class: Log S scale |
Very soluble |
| Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-0.31 |
| Solubility | 55.8 mg/ml ; 0.489 mol/l |
| Class? Solubility class: Log S scale |
Soluble |
| 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) |
No |
| CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
No |
| CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
| CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
| CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
| CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
| Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-7.22 cm/s |
| Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
| Ghose? Ghose filter: implemented from |
None |
| Veber? Veber (GSK) filter: implemented from |
0.0 |
| Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
| Muegge? Muegge (Bayer) filter: implemented from |
1.0 |
| Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
| PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
| Brenk? Structural Alert: implemented from |
0.0 alert: heavy_metal |
| Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
| Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.81 |
* 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 |
|---|---|---|
| 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 |
[ 21436-03-3 ]
[ 34595-26-1 ]
| Yield | Reaction Conditions | Operation 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)+. |
[ 21436-03-3 ]
[ 147702-14-5 ]


| Yield | Reaction Conditions | Operation 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. |
[ 21436-03-3 ]
[ 147702-14-5 ]



| Yield | Reaction Conditions | Operation 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. |

A1079982 [35018-62-3]
(1S,2S)-Cyclohexane-1,2-diamine dihydrochloride
Reason: Free-salt

A1471231 [20439-47-8]
(1R,2R)-Cyclohexane-1,2-diamine
Reason:

A103470 [20439-47-8]
(1R,2R)-Cyclohexane-1,2-diamine
Reason: Optical isomers

A260837 [99363-25-4]
trans-Cyclopentane-1,2-diamine dihydrochloride
Similarity: 0.82