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Chemical Structure| 611-14-3 Chemical Structure| 611-14-3
Chemical Structure| 611-14-3

1-Ethyl-2-methylbenzene

CAS No.: 611-14-3

4.5 *For Research Use Only !

Cat. No.: A373861 Purity: 98%

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Product Citations

Product Citations

Luca Léo Schmermund ;

Abstract: The limited resources on Earth as well as the energy demand of the ever-increasing population urges us to develop new sustainable processes that cover the use of renewable energy and raw materials. In this context, coupling light with biological systems or enzymes for chemical synthesis is one possible way to achieve sustainable processes as light is a powerful and almost ideal source of energy. In recent years, the field of photobiocatalysis has emerged which brought together two sustainable as well as two research-intensive fields: Photocatalysis and biocatalysis. In this thesis, photo(bio)catalytic transformations were investigated employing light-dependent protochlorophyllide oxidoreductases and an unspecific peroxygenase. In the first part of this study, the library of light-dependent protochlorophyllide oxidoreductases (LPORs) was expanded and the potential of LPORs as biocatalysts was explored. LPORs require light for their natural reaction and catalyze the NADPH-dependent reduction of a C=C in an N-heterocycle of protochlorophyllide, a precursor of chlorophyll. Five LPORs were identified by a sequence search and four of them were well expressible in Escherichia coli and displayed activity. Overall, the study showed that LPORs are easily accessible and possess properties that are required for an efficient biocatalyst. In the second part of this thesis, a light-driven in situ generation of hydrogen peroxide by different carbon nitrides (CNs) was linked to stereoselective hydroxylations catalyzed by an unspecific peroxygenase variant from Agrocybe aegerita (AaeUPO). The chromoselective behavior of the CN allowed to create photo-chemo-enzymatic cascades to form either the (S)- or the (R)-enantiomer of 1-phenylethanol starting from ethylbenzene. The combination of chromoselective photocatalysis with biocatalytic transformation was shown for the first time. The novel concept represents a new tool for controlling reactivity and stereoselectivity in organic synthesis leading to excellent stereoselectivities.

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Product Details of [ 611-14-3 ]

CAS No. :611-14-3
Formula : C9H12
M.W : 120.19
SMILES Code : CC1=CC=CC=C1CC
MDL No. :MFCD00009257
InChI Key :HYFLWBNQFMXCPA-UHFFFAOYSA-N
Pubchem ID :11903

Safety of [ 611-14-3 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H225-H304
Precautionary Statements:P301+P310-P331
Class:3
UN#:3295
Packing Group:

Calculated chemistry of [ 611-14-3 ] Show Less

Physicochemical Properties

Num. heavy atoms 9
Num. arom. heavy atoms 6
Fraction Csp3 0.33
Num. rotatable bonds 1
Num. H-bond acceptors 0.0
Num. H-bond donors 0.0
Molar Refractivity 41.18
TPSA ?

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

0.0 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.24
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

3.53
Log Po/w (WLOGP)?

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

2.56
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.

4.17
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

3.13
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

3.13

Water Solubility

Log S (ESOL):?

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

-3.24
Solubility 0.0697 mg/ml ; 0.00058 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.

-3.21
Solubility 0.0734 mg/ml ; 0.000611 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

-3.53
Solubility 0.0357 mg/ml ; 0.000297 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.

-4.53 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

1.0
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<2.0
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)

1.0

Application In Synthesis of [ 611-14-3 ]

* 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 [ 611-14-3 ]

[ 611-14-3 ] Synthesis Path-Downstream   1~28

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  • [ 102879-53-8 ]
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  • [ 611-15-4 ]
  • [ 611-14-3 ]
YieldReaction ConditionsOperation in experiment
67%Spectr. With triethylsilane; fluorotris(pentafluorophenyl)phosphonium tetrakis(pentafluorophenyl)borate; para-thiocresol; at 25℃; for 1h; General procedure: To a solution of silane(1.0 Eq), RH (R = Ar2N, ArS, ArO, ArCO2) (1.0 Eq) and olefin (1.0-1.2 Eq) wasadded the [(C6F5)3PF][B(C6F5)4] (1.5 mol%) in C6D5Br or CD2Cl2 (0.5 M) at 25 C. The reaction was monitored by NMR or TLC until completion. Yieldwas determined by 1H-NMR spectroscopy. For isolated yields, the reactionwas quenched with a diluted solution of NaHCO3 and the mixture wasextracted with CH2Cl2. The organic solution was dried over MgSO4, filtered,and evaporated. The crude was diluted with hexane and filtered over silica gel; products were eluted with hexane and Et2O for dibutyl 2-methylenesuccinate. The quality of the catalyst is again essential for the successful completion of the reaction
  • 13
  • [ 71028-31-4 ]
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  • [ 615-37-2 ]
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  • 16
  • [ 119-65-3 ]
  • [ 91-20-3 ]
  • [ 119-64-2 ]
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  • [ 253185-02-3 ]
  • 17
  • [ 120-72-9 ]
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  • [ 1678-91-7 ]
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  • 18
  • [ 34557-54-5 ]
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  • [ 98-51-1 ]
  • [ 1075-38-3 ]
  • [ 108-88-3 ]
  • 19
  • [ 74-85-1 ]
  • [ 75-28-5 ]
  • [ 620-14-4 ]
  • [ 611-14-3 ]
  • [ 622-96-8 ]
  • 20
  • [ 95-47-6 ]
  • [ 95-65-8 ]
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  • [ 95-63-6 ]
  • [ 526-75-0 ]
  • [ 89-95-2 ]
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  • 21
  • [ 95-47-6 ]
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  • [ 95-63-6 ]
  • [ 526-73-8 ]
  • [ 89-95-2 ]
  • [ 952-80-7 ]
  • 22
  • [ 14531-53-4 ]
  • [ 100-41-4 ]
  • [ 620-14-4 ]
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  • [ 622-96-8 ]
  • 24
  • [ 611-14-3 ]
  • [ 2229-07-4 ]
  • [ 2348-48-3 ]
  • 26
  • [ 611-14-3 ]
  • [ 35106-84-4 ]
YieldReaction ConditionsOperation in experiment
203 g With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; for 2h;Reflux; A stirred mixture of 1-ethyl-2-methylbenzene (commercial, 50 g, 416 mmol), N25 bromosuccinimide (155 g, 874 mmol) and benzoyl peroxide (6.72 g, 20.80 mmol) in carbon tetrachloride Ci .25 L) was heated to reflux. After 2 h, the reaction mixture was allowed to warm to rt, then poured onto an aqueous saturated solution of Na2CO3 (1 L). The organic layer was successively washed with an aqueous saturated solution of Na2003 (0.5 L), brine (0.5 L) and dried over Na2SO4, filtered and concentrated under vacuum to obtain 203 g of 1-(1-bromoethyl)-2-(bromomethyl)benzene a20 as a yellow oil which was used in next step without any further purification.GO-MS (El-positive): 199/201 [M-Br].
  • 27
  • [ 533-18-6 ]
  • [ 292638-84-7 ]
  • [ 611-14-3 ]
  • [ 694-87-1 ]
  • 28
  • [ 201230-82-2 ]
  • [ 611-15-4 ]
  • [ 611-14-3 ]
  • [ 103108-03-8 ]
 

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