3-Methylstyrene

Cat.NO.:A413069 Purity:97% (stabilized with TBC)

Product Details of [ 100-80-1 ]

CAS No. :	100-80-1
Formula :	C₉H₁₀
M.W :	118.18
SMILES Code :	C=CC1=CC(C)=CC=C1
MDL No. :	MFCD00008617
InChI Key :	JZHGRUMIRATHIU-UHFFFAOYSA-N
Pubchem ID :	7529

Safety of [ 100-80-1 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H225-H304-H315-H319-H332-H335
Precautionary Statements:	P261-P301+P310-P305+P351+P338-P331
Class:	3
UN#:	1993
Packing Group:	Ⅲ

Computational Chemistry of [ 100-80-1 ] Show Less

Physicochemical Properties

Num. heavy atoms	9
Num. arom. heavy atoms	6
Fraction Csp3	0.11
Num. rotatable bonds	1
Num. H-bond acceptors	0.0
Num. H-bond donors	0.0
Molar Refractivity	41.5
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	0.0 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.25
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	3.35
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.53
Log P_o/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.	4.08
Log P_o/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	3.12
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	3.07

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.11
Solubility	0.0916 mg/ml ; 0.000775 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.	-3.03
Solubility	0.111 mg/ml ; 0.000939 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	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	-3.18
Solubility	0.0784 mg/ml ; 0.000664 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	Low
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
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.	-4.64 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	2.0
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)	1.21

Application In Synthesis of [ 100-80-1 ]

* 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 [ 100-80-1 ]

[ 100-80-1 ] Synthesis Path-Downstream 1~2

1
[ 943835-77-6 ]
[ 100-80-1 ]
[ 1244036-19-8 ]

References: [1]European Journal of Organic Chemistry,2010,p. 4211 – 4217.

2
[ 100-80-1 ]
[ 51012-64-7 ]

Yield	Reaction Conditions	Operation in experiment
82%	With dibromamine-T; sodium thiosulfate; In water; acetone; at 20℃; for 2h;	General procedure: To a solution of olefin (1mmol) in acetone (3mL) and water (0.1mL), TsNBr2 (2.2mmol) was added at room temperature. After completion of reaction, sodium thiosulfate (200mg approx.) was added and the reaction mixture was stirred for another 10min. The reaction mixture was extracted with ethyl acetate, dried (Na2SO4) and concentrated. Purification of the crude product by flash chromatography on silica gel (230-400 mesh) with petroleum ether-EtOAc as eluent gave the pure product.
	With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; water; In acetone; at 70℃; for 0.138833h;	Dissolve 5mmol (0.59g) of 3-methylstyrene in 10mL 1:1 water/acetone solution (5mL water plus 5mL acetone mixedIn homogeneous), a homogeneous solution A was obtained, which was added to the syringe pump a; 8 mmol (2.29 g) of DBH was dissolved in 10 mL of 1:1 water/acetone solution.In a solution (5 ml of water plus 5 ml of acetone mixed uniformly), a homogeneous solution B was obtained, which was added to a syringe pump b; 6 mmol (0.91 g) of DBU was added.And 6mmol (1.10g) of pentafluorophenol dissolved in 10mL of acetone (acetone) to obtain a homogeneous solution C, added to the syringe pump c; injectionThe injection flow rates of pumps a and b were both 0.3 ml/min, and the injection flow rate of syringe pump c was 0.5 ml/min; the first microchannel reactor was reversed.The volume V=5ml, the reaction time 8.33min, the second microchannel reactor reaction volume V=5ml, the reaction time is 4.55min;First and second microchannel reactor inner diameter = 0.5 mm; first microchannel reactor temperature is 70 C, second microchannel reactorThe temperature is 60 C; after two cycles of the second microchannel reactor reaction, the reaction liquid is collected and calculated by HPLC method.The product yield was 74%.Separation by column chromatography to obtain product 3i

References: [1]Tetrahedron Letters,2015,vol. 56,p. 356 – 358.
[2]Organic and Biomolecular Chemistry,2016,vol. 14,p. 11389 – 11395.
[3]Organic and Biomolecular Chemistry,2017,vol. 15,p. 9889 – 9894.
[4]Patent: CN109824494,2019,A .Location in patent: Paragraph 0052-0053.
[5]Chinese Journal of Chemistry,2020,vol. 38,p. 173 – 177.

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