132547-64-9

Basic information

• Product Name: Carbamic acid, (3-butenyl)-, phenylmethyl ester
• CAS NO: 132547-64-9
• Molecular Formula: C12H15NO2
• Molecular Weight: 205.257
• Mol File: 132547-64-9.mol
• Article Data: 12

Chemical Properties

• CAS DataBase Reference: Carbamic acid, (3-butenyl)-, phenylmethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, (3-butenyl)-, phenylmethyl ester(132547-64-9)
• EPA Substance Registry System: Carbamic acid, (3-butenyl)-, phenylmethyl ester(132547-64-9)

Safety Data

• Hazardous Substances Data: 132547-64-9(Hazardous Substances Data)

Upstream product

• 2524-49-4 3-butene-1-amine 
• 100-51-6 benzyl alcohol 
• 1138-80-3 N-(Benzyloxycarbonyl)glycine 
• 96921-56-1 Allyl N-(benzyloxycarbonyl)glycinate 
• 1029033-63-3 but-3-ene-1-amine hydrobromide 
• 501-53-1 benzyl chloroformate 
• 17875-18-2 but-3-en-1-amine hydrochloride 

Downstream Products

• 1333401-24-3 C₁₃H₁₅NO₅ 
• 1072792-94-9 {2-[(rac)-3-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-2-oxo-oxazolidin-5-yl]-ethyl}-carbamic acid benzyl ester 
• 1072792-93-8 [(rac)-4-(2,3-dihydro-benzo[1,4]dioxin-6-ylamino)-3-hydroxy-butyl]-carbamic acid benzyl ester 
• 1072792-91-6 toluene-4-sulfonic acid (rac)-4-benzyloxycarbonylamino-2-hydroxy-butyl ester 
• 1072792-92-7 benzyl (2-(oxiran-2-yl)ethyl)carbamate 
• 916982-50-8 benzyl N-(but-3-enyl)-N-(trimethylsilylethynyl)carbamate 
• 946659-01-4 [(rac)-3,4-dihydroxy-butyl]-carbamic acid benzyl ester 
• 882529-61-5 benzyl but-3-en-1-yl[2-oxo-3-(triphenyl-λ⁵-phosphoranylidene)prop-1-yl]carbamate 
• 882529-65-9 benzyl but-3-en-1-yl(2-oxopent-3-en-1-yl)carbamate 

Relevant articles and documents

New insights into structure–activity relationship of ipomoeassin F from its bioisosteric 5-oxa/aza analogues

Ipomoeassin F, a plant-derived macrolide, exhibited single-digit nanomolar growth inhibition activity against many cancer cell lines. In this report, a series of 5-oxa/aza analogues was prepared and screened for cytotoxicity. Replacement of 5-CH2 with O/NH simplified the synthesis and led to only a small activity loss. N-methylation almost completely restored the potency. Further studies with additional 5-oxa analogues suggested, for the first time, that size and flexibility of the ring also significantly influence the bioactivity of ipomoeassin F.

Carbamate Synthesis Using a Shelf-Stable and Renewable C1 Reactant

4-Propylcatechol carbonate is a shelf-stable, renewable C1 reactant. It is easily prepared from renewable 4-propylcatechol (derived from wood) and dimethyl carbonate (derived from CO2) using a reactive distillation system. In this work, the 4-propylcatechol carbonate is used for the two-step synthesis of carbamates under mild reaction conditions. In the first step, 4-propylcatechol carbonate is treated with an alcohol at 50–80 °C in the presence of a Lewis acid catalyst, such as Zn(OAc)2?2 H2O. With liquid alcohols, no solvent is used and with solid alcohols 2-methyltetrahydrofuran is used as solvent. In the second step, the alkyl 2-hydroxy-propylphenyl carbonate intermediates obtained react with amines at room temperature in 2-methyltetrahydrofuran, forming the target carbamates and the byproduct 4-propylcatechol, which can be recycled into a carbonate reactant.

Dual Catalytic Decarboxylative Allylations of α-Amino Acids and Their Divergent Mechanisms

The room temperature radical decarboxylative allylation of N-protected α-amino acids and esters has been accomplished via a combination of palladium and photoredox catalysis to provide homoallylic amines. Mechanistic investigations revealed that the stability of the α-amino radical, which is formed by decarboxylation, dictates the predominant reaction pathway between competing mechanisms.