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[ CAS No. 611-14-3 ] {[proInfo.proName]}

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Chemical Structure| 611-14-3
Chemical Structure| 611-14-3
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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 MDL No. :MFCD00009257
Formula : C9H12 Boiling Point : -
Linear Structure Formula :- InChI Key :HYFLWBNQFMXCPA-UHFFFAOYSA-N
M.W : 120.19 Pubchem ID :11903
Synonyms :

Calculated chemistry of [ 611-14-3 ]      Expand+

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 : 0.0 ?2

Pharmacokinetics

GI absorption : Low
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.53 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.24
Log Po/w (XLOGP3) : 3.53
Log Po/w (WLOGP) : 2.56
Log Po/w (MLOGP) : 4.17
Log Po/w (SILICOS-IT) : 3.13
Consensus Log Po/w : 3.13

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.24
Solubility : 0.0697 mg/ml ; 0.00058 mol/l
Class : Soluble
Log S (Ali) : -3.21
Solubility : 0.0734 mg/ml ; 0.000611 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.53
Solubility : 0.0357 mg/ml ; 0.000297 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 1.0

Safety of [ 611-14-3 ]

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

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   1~12

  • 1
  • [ 932-31-0 ]
  • [ 64-67-5 ]
  • [ 611-14-3 ]
  • 2
  • [ 74-96-4 ]
  • [ 95-46-5 ]
  • [ 611-14-3 ]
  • 3
  • [ 111-84-2 ]
  • [ 611-14-3 ]
  • 6
  • [ 611-14-3 ]
  • [ 102879-53-8 ]
  • [ 102877-99-6 ]
  • 10
  • [ 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
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