[ CAS No. 102-93-2 ] {[proInfo.proName]}

Name: 102-93-2|3-Phenylpropanamide|98%
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3d Animation Molecule Structure of 102-93-2

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Quality Control of [ 102-93-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 102-93-2 ]

SDS Specification

Alternatived Products of [ 102-93-2 ]

Product Citations

Surveying the scope of aromatic decarboxylations catalyzed by prenylated-flavin dependent enzymes

Anushree Mondal ; Pronay Roy ; Jaclyn Carrannatto , et al. Faraday Discuss.,2024. DOI: 10.1039/D4FD00006D PubMed ID: 38837123

Abstract: The prenylated-flavin mononucleotide-dependent decarboxylases (also known as UbiD-like enzymes) are the most recently discovered family of decarboxylases. The modified flavin facilitates the decarboxylation of unsaturated carboxylic acids through a novel mechanism involving 1,3-dipolar cyclo-addition chemistry. UbiD-like enzymes have attracted considerable interest for biocatalysis applications due to their ability to catalyse (de)carboxylation reactions on a broad range of aromatic substrates at otherwise unreactive carbon centres. There are now ∼35[thin space (1/6-em)]000 protein sequences annotated as hypothetical UbiD-like enzymes. Sequence similarity network analyses of the UbiD protein family suggests that there are likely dozens of distinct decarboxylase enzymes represented within this family. Furthermore, many of the enzymes so far characterized can decarboxylate a broad range of substrates. Here we describe a strategy to identify potential substrates of UbiD-like enzymes based on detecting enzyme-catalysed solvent deuterium exchange into potential substrates. Using ferulic acid decarboxylase (FDC) as a model system, we tested a diverse range of aromatic and heterocyclic molecules for their ability to undergo enzyme-catalysed H/D exchange in deuterated buffer. We found that FDC catalyses H/D exchange, albeit at generally very low levels, into a wide range of small, aromatic molecules that have little resemblance to its physiological substrate. In contrast, the sub-set of aromatic carboxylic acids that are substrates for FDC-catalysed decarboxylation is much smaller. We discuss the implications of these findings for screening uncharacterized UbiD-like enzymes for novel (de)carboxylase activity.

Purchased from AmBeed: 27916-43-4 ; 2438-05-3 ; 501-89-3 ; 42287-94-5 ; 776-79-4 ; 53473-36-2 ; 7251-61-8 ; 42287-97-8 ; 1621-91-6 ; 37718-11-9 ; 288-13-1 ; 86-73-7 ; 104-53-0 ; 2018-90-8 ; 87-66-1 ; 135-19-3 ; 1664-57-9 ; 289-80-5 ; 693-95-8 ; 55-22-1 ; 102-93-2 ; 1477-50-5 ; 1632-76-4 ; 4780-79-4 ; 16642-79-8 ; 3581-89-3 ; 501-97-3 ; 771-50-6 ; 98-98-6 ; 619-64-7 ; 100-51-6 ; 402-45-9 ; 59-67-6 ; 93-60-7 ; 273-53-0 ; 2084-13-1 ; 51-17-2 ; 2459-09-8 ; 2459-07-6 ; 95-16-9 ; 459-31-4 ; 90-05-1 ; 150-76-5 ; 103-25-3 ; 271-44-3 ; 6293-56-7 ; 2550-26-7 ; 288-32-4 ; 501-52-0 ; 2001-32-3 ; 1592-38-7 ; 95-15-8 ; 91-19-0 ; 1122-61-8 ; 3724-19-4 ; 20173-24-4 ; 118-31-0 ; 6125-24-2 ; 60-12-8 ; 90-15-3 ; 120-72-9 ; 822-36-6 ; 288-47-1 ; 288-42-6 ; 2038-57-5 ; 38628-51-2 ; 1929-29-9 ; 15009-91-3 ; 1505-50-6 ; 581-40-8 ; 616-47-7 ; 1571-33-1 ...More

Product Details of [ 102-93-2 ]

CAS No. :	102-93-2	MDL No. :	MFCD00025535
Formula :	C₉H₁₁NO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VYIBCOSBNVFEIW-UHFFFAOYSA-N
M.W :	149.19	Pubchem ID :	7625
Synonyms :

Calculated chemistry of [ 102-93-2 ] Expand+

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.22
Num. rotatable bonds :	3
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	43.93
TPSA :	43.09 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.56 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.45
Log Po/w (XLOGP3) :	0.91
Log Po/w (WLOGP) :	1.1
Log Po/w (MLOGP) :	1.58
Log Po/w (SILICOS-IT) :	1.64
Consensus Log Po/w :	1.34

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.54
Solubility :	4.26 mg/ml ; 0.0286 mol/l
Class :	Very soluble
Log S (Ali) :	-1.4
Solubility :	5.93 mg/ml ; 0.0398 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.78
Solubility :	0.249 mg/ml ; 0.00167 mol/l
Class :	Soluble

Medicinal Chemistry

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

Safety of [ 102-93-2 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 102-93-2 ]

* 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.

Upstream synthesis route of [ 102-93-2 ]
Downstream synthetic route of [ 102-93-2 ]

[ 102-93-2 ] Synthesis Path-Upstream 1~1

1
[ 102-93-2 ]
[ 6970-83-8 ]

Reference： [1] Recueil des Travaux Chimiques des Pays-Bas, 1906, vol. 25, p. 243

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Isomers

Technical Information

• 1,4-Addition of an Amine to a Conjugated Enone • 1,4-Addition of an Amine to a Conjugated Enone • Acyl Group Substitution • Amide Hydrolysis • Amide Hydrolysis • Amides Can Be Converted into Aldehydes • Amine Synthesis from Nitriles • Amine Synthesis from Nitriles • Amines Convert Acyl Chlorides into Amides • Amines Convert Esters into Amides • Azide Reduction by LiAlH4 • Azide Reduction by LiAlH4 • Basicity of Amines • Benzylic Oxidation • Birch Reduction • Birch Reduction of Benzene • Blanc Chloromethylation • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chan-Lam Coupling Reaction • Chichibabin Reaction • Complete Benzylic Oxidations of Alkyl Chains • Complete Benzylic Oxidations of Alkyl Chains • Complex Metal Hydride Reductions • Conversion of Amino with Nitro • Deprotonation of Methylbenzene • Diazotization Reaction • DIBAL Attack Nitriles to Give Ketones • Directing Electron-Donating Effects of Alkyl • Electrophilic Chloromethylation of Polystyrene • Enamine Formation • Formation of an Amide from an Amine and a Carboxylic Acid • Formation of an Amide from an Amine and a Carboxylic Acid • Friedel-Crafts Alkylation of Benzene with Acyl Chlorides • Friedel-Crafts Alkylation of Benzene with Carboxylic Anhydrides • Friedel-Crafts Alkylation Using Alkenes • Friedel-Crafts Alkylations of Benzene Using Alkenes • Friedel-Crafts Alkylations Using Alcohols • Friedel-Crafts Reaction • Groups that Withdraw Electrons Inductively Are Deactivating and Meta Directing • Halogenation of Benzene • Hemiaminal Formation from Amines and Aldehydes or Ketones • Hemiaminal Formation from Amines and Aldehydes or Ketones • Hofmann Elimination • Hofmann Rearrangement • Hydride Reductions • Hydrogenation to Cyclohexane • Hydrogenolysis of Benzyl Ether • Hydrolysis of Imines to Aldehydes and Ketones • Imine Formation from Amines and Aldehydes or Ketones • Lawesson's Reagent • Leuckart-Wallach Reaction • Mannich Reaction • Methylation of Ammonia • Methylation of Ammonia • Nitration of Benzene • Nitrosation of Amines • Nucleophilic Aromatic Substitution • Nucleophilic Aromatic Substitution with Amine • Oxidation of Alkyl-substituted Benzenes Gives Aromatic Ketones • Peptide Bond Formation with DCC • Petasis Reaction • Preparation of Alkylbenzene • Preparation of Amines • Preparation of LDA • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reduction of an Amide to an Amine • Reduction of an Amide to an Amine • Reductive Amination • Reductive Amination • Reductive Removal of a Diazonium Group • Reverse Sulfonation——Hydrolysis • Ring Opening of Azacyclopropanes • Ring Opening of Azacyclopropanes • Ring Opening of Oxacyclobutanes • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Specialized Acylation Reagents-Ketenes • Specialized Acylation Reagents-Vilsmeier Reagent • Strecker Synthesis • Sulfonation of Benzene • Synthesis of 2-Amino Nitriles • The Acylium Ion Attack Benzene to Form Phenyl Ketones • The Claisen Rearrangement • The Nitro Group Conver to the Amino Function • Ugi Reaction • Vilsmeier-Haack Reaction

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Yield	Reaction Conditions	Operation in experiment
79%	at 295℃; for 1h;	General procedure: Following the amide intermediate Preparation Example A. The reaction vessel is closed (when the amide intermediate has a boiling point at normal pressure equal to or lower than the reaction temperature TB described below) or the reaction vessel is kept open (when the amide intermediate has a boiling point higher than the normal pressure When the reaction temperature is TB), stirring is continued (600 r/min), the reaction temperature is changed to TB, and after the reaction temperature TB is maintained for TD hours, the reaction is substantially completed. Then, the reaction vessel was sealed and connected to a vacuum pump so that the degree of vacuum in the reaction vessel reached 20-50 mbar (according to the type of nitrile product) and the distillate was used as the nitrile product. The yield of the nitrile product was calculated and sampled for nuclear magnetic resonance and elemental analysis to characterize the nitrile product obtained. Specific reaction conditions and characterization results are shown in Tables A-7, A-8, A-9, A-10, A-11 and A-12 below. These characterization results show that the nitrile product obtained has an extremely high purity (above 99%).In these nitrile product preparation examples, 10 g of phosphorus pentaoxide is preferably added to the reaction vessel as a catalyst at one stage, optionally at the beginning of the reaction.
74%	With triethylamine; ethanaminium,N-(difluoro-lambda4-sulfanylidene)-N-ethyl-,tetrafluoroborate; In ethyl acetate; at 20℃; for 1h;Inert atmosphere;	General procedure: To a solution of the aldoxime or the amide (1.0 mmol) and Et3N (1.5mmol) in EtOAc (1 mL, 1 M) at r.t. was added XtalFluor-E8 (1.1 mmol)portionwise over ca. 2 min. The resulting solution was stirred at r.t.for 1 h. The reaction mixture was quenched with sat. aq Na2CO3 and extracted with CH2Cl2 (2 × 10 mL). The combined organic layers were washed with H2O and brine, dried (MgSO4), and concentrated under vacuum to afford the crude nitrile, which was purified by flash chromatography, if required.

Yield	Reaction Conditions	Operation in experiment
92%	With dibromamine-T; 1,8-diazabicyclo[5.4.0]undec-7-ene; for 0.333333h;Reflux;	General procedure: To a solution of amide (1 mmol) in methanol (10 mL) was added DBU (0.5 mL). To this solution TsNBr2 (1 mmol) was added. The reaction mixture was heated under reflux condition for a period of 10-20 min (TLC). After completion of the reaction (TLC) methanol was evaporated under reduced pressure. The crude mixture was then dissolved in EtOAc. This solution was washed with 5% HCl and then with saturated Na2CO3 solution. The organic extracts were separated and dried over anhydrous Na2SO4. The crude product was purified by flash column chromatography using petroleum ether and ethyl acetate (4:1) as eluent to get the pure carbamate product.
83%	With lithium hydroxide monohydrate; N-bromoacetamide; at 0 - 25℃; for 24h;Darkness;	General procedure: To a solution of a carboxamide 1 (0.6-7 mmol) in MeOH (0.2-0.9 M) was added LiOH·H2O (2-15 equiv), with the flask protected from light and cooled to 0 C with stirring. Solid NBA (1-8 equiv) was added in one portion and the heterogeneous mixture was stirred, while the temperature gradually attained r.t. The reaction progress was monitored by TLC, requiring 24-48 h for completion. The reaction mixture was added to 10% aqueous Na2S2O5 (2 volumes) and concentrated on a rotary evaporator (30 C, 30 min). The liquid residue was diluted with 5% aqueous NaOH (15 volumes) and extracted with CH2Cl2 (3 × 8 volumes). The combined extracts were concentrated on a rotary evaporator and vacuum-dried (0.2 mmHg, 40 C, 1 h). Further purification, when necessary, was achieved by dry-column flash chromatography, using the solvent gradient as indicated. When BnOH was used instead of MeOH, the procedure was modified as follows: After reaction completion, the mixture was diluted with CH2Cl2(25 volumes) and extracted successively with 10% aqueous Na2S2O5 (2 volumes) and 5% aqueous NaOH (15 volumes). The organic layer was concentrated on a rotary evaporator and the excess BnOH was removed under reduced pressure (0.2 mm Hg, 80 C, 45 min). When necessary, the product was purified by dry-column flash chromatography.

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H231	May react explosively even in the absence of air at elevated pressure and/or temperature
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Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 102-93-2 ] {[proInfo.proName]}

Quality Control of [ 102-93-2 ]

Related Doc. of [ 102-93-2 ]

Product Citations

Product Details of [ 102-93-2 ]

Calculated chemistry of [ 102-93-2 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 102-93-2 ]

Application In Synthesis of [ 102-93-2 ]

[ 102-93-2 ] Synthesis Path-Upstream 1~1

[ 102-93-2 ] Synthesis Path-Downstream 1~109

Technical Information

Related Functional Groups of [ 102-93-2 ]

Aryls

Amides

Amines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 102-93-2 ]