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Type | HazMat fee for 500 gram (Estimated) |
Excepted Quantity | USD 0.00 |
Limited Quantity | USD 15-60 |
Inaccessible (Haz class 6.1), Domestic | USD 80+ |
Inaccessible (Haz class 6.1), International | USD 150+ |
Accessible (Haz class 3, 4, 5 or 8), Domestic | USD 100+ |
Accessible (Haz class 3, 4, 5 or 8), International | USD 200+ |
Structure of 611-14-3
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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.
4.5
*For Research Use Only !
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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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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 |
GHS Pictogram: |
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Signal Word: | Danger |
Hazard Statements: | H225-H304 |
Precautionary Statements: | P301+P310-P331 |
Class: | 3 |
UN#: | 3295 |
Packing Group: | Ⅱ |
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 |
0.0 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.24 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.53 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.56 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
4.17 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.13 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
3.13 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.24 |
Solubility | 0.0697 mg/ml ; 0.00058 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.21 |
Solubility | 0.0734 mg/ml ; 0.000611 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.53 |
Solubility | 0.0357 mg/ml ; 0.000297 mol/l |
Class? Solubility class: Log S scale |
Soluble |
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) |
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 |
-4.53 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
1.0 |
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 |
2.0 |
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<2.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.0 |
* 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 |
---|---|---|
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 |
Yield | Reaction Conditions | Operation 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]. |
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