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Chemical Structure| 1191-67-9 Chemical Structure| 1191-67-9

Structure of Decane-1,10-dithiol
CAS No.: 1191-67-9

Chemical Structure| 1191-67-9

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Product Citations

Product Citations

Alfarhan, Saleh ; Chen, Mengdi ; Huish, Jackson ; Jin, Kailong ;

Abstract: Current photopolymers are mainly produced by (meth)acrylate-based photoresins, possessing permanently cross-linked structures that prohibit their chemical recycling. This study reports a one-step, scalable synthesis of dynamically cross-linked semicrystalline thiol–ene photopolymers comprising exchangeable disulfide bonds with excellent material performance, shape memory/adaptive characteristics, and chemical recyclability. These photopolymers are synthesized via stoichiometric thiol–ene click reactions using commercial reagents, including difunctional ene, alkyl dithiol giving rise to crystallinity, thiol-terminated oligomer comprising dynamic disulfide bonds, and trithiol cross-linker. Cross-link density is systematically controlled by varying trithiol cross-linker content to tune degrees of crystallinity and mechanical properties over a wide range, e.g., Young’s modulus from 4 to 138 MPa, elongation-at-break from 40 to 370%, and toughness from 0.3 to 32 MJ m−3. Importantly, these dynamically cross-linked photopolymers undergo complete decross-linking via thiol-disulfide exchange reactions with small-molecule thiols at 120 °C in a solvent- and catalyst-free manner, yielding liquid thiolterminated oligomers. These recycled thiol-terminated oligomers are used to synthesize next-generation dynamically cross-linked thiol–ene photopolymers with identical material composition and full property retention, demonstrating closed-loop recycling. Promisingly, these new thiol–ene photoresins demonstrate excellent feasibility for Digital Light Processing (DLP)-based 3D printing of high-resolution objects with complex geometries, preserved crystallinity and recyclability, and unique shape memory/adaptive characteristics.

Keywords: 3D printing ; chemical recycling ; cross-linked semicrystalline thiol–ene photopolymer ; dynamic covalent bonds ; shape-memory materials

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Product Details of [ 1191-67-9 ]

CAS No. :1191-67-9
Formula : C10H22S2
M.W : 206.41
SMILES Code : SCCCCCCCCCCS
MDL No. :MFCD00022095
InChI Key :UOQACRNTVQWTFF-UHFFFAOYSA-N
Pubchem ID :14494

Safety of [ 1191-67-9 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H315-H319-H413-H372
Precautionary Statements:P501-P273-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313
Class:9
UN#:3335
Packing Group:

Computational Chemistry of [ 1191-67-9 ] Show Less

Physicochemical Properties

Num. heavy atoms 12
Num. arom. heavy atoms 0
Fraction Csp3 1.0
Num. rotatable bonds 9
Num. H-bond acceptors 0.0
Num. H-bond donors 0.0
Molar Refractivity 66.04
TPSA ?

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

77.6 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

3.19
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

4.4
Log Po/w (WLOGP)?

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

3.97
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.

3.91
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

4.0
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

3.89

Water Solubility

Log S (ESOL):?

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

-3.3
Solubility 0.104 mg/ml ; 0.000504 mol/l
Class?

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

Soluble
Log S (Ali)?

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

-5.75
Solubility 0.00037 mg/ml ; 0.00000179 mol/l
Class?

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

Moderately 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

-4.16
Solubility 0.0144 mg/ml ; 0.00007 mol/l
Class?

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

Moderately 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

Yes
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

Yes
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.

-4.44 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

0.0
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

1.0 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<3.0
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)

2.56
 

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