7693-41-6

Usage

Uses

4-Methoxyphenyl Chloroformate is a useful reagent in epoxidation reactions.

Chemical Properties

clear colorless to pale yellow liquid

InChI:InChI=1/C8H7ClO3/c1-11-6-2-4-7(5-3-6)12-8(9)10/h2-5H,1H3

Upstream product

• 75-44-5 phosgene 
• 1122-95-8 sodium 4-methoxyphenolate 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 150-76-5 4-methoxy-phenol 
• 503-38-8 trichloromethyl chloroformate 

Downstream Products

• 35684-14-1 4-n-Butyl-phenyl-4'-anisoyl-carbonat 
• 31364-71-3 (1-Methyl-2-phenyl-ethyl)-carbamic acid 4-methoxy-phenyl ester 
• 57490-68-3 N-(4-Methoxyphenoxycarbonyl)-6-aminohexansaeure 
• 77637-84-4 p-methoxyphenyl 2-pyridylethyl carbonate 
• 122734-37-6 (2-Dimethylamino-ethyl)-methyl-carbamic acid 4-methoxy-phenyl ester 
• 40438-26-4 C₂₆H₂₂NO₃P 
• 31558-44-8 p-Methoxybenzyl-p-methoxyphenyl-carbonat 
• 31594-17-9 3,4-Dimethoxybenzyl-p-methoxyphenyl-carbonat 
• 175023-51-5 4-methoxyphenyl 4-nitrophenyl carbonate 
• 19219-48-8 4-methoxyphenyl N-phenylcarbamate 
• 150-76-5 4-methoxy-phenol 

Relevant academic research and scientific papers

In vitro radical scavenging and cytotoxic activities of novel hybrid selenocarbamates

Novel selenocyanate and diselenide derivatives containing a carbamate moiety were synthesised and evaluated in vitro to determine their cytotoxic and radical scavenging properties. Cytotoxic activity was tested against a panel of human cell lines including CCRF-CEM (lymphoblastic leukaemia), HT-29 (colon carcinoma), HTB-54 (lung carcinoma), PC-3 (prostate carcinoma), MCF-7 (breast adenocarcinoma), 184B5 (non-malignant, mammary gland derived) and BEAS-2B (non-malignant, derived from bronchial epithelium). Most of the compounds displayed high antiproliferative activity with GI50 values below 10 μM in MCF-7, CCRF-CEM and PC-3 cells. Radical scavenging properties of the new selenocompounds were confirmed testing their ability to scavenge DPPH and ABTS radicals. Based on the activity of selenium-based glutathione peroxidases (GPxs), compounds 1a, 2e and 2h were further screened for their capacity to reduce hydrogen peroxide under thiol presence. Results suggest that compound 1a mimics GPxs activity. Cytotoxic parameters, radical scavenging activity and ADME profile point to 1a as promising drug candidate.

Synthesis of C2-symmetric bisphosphine ligands from tartaric acid, and their performance in the Pd-Catalyzed asymmetric o-allylation of a phenol

Starting from tartaric acid derived chiral diols or dicarboxylic acid dichlorides with either a 2,2-dimethyl-1,3-dioxolane (Taddol) or a 2,3-dimethoxy-2,3-dimethyl-1,4-dioxane (Tatrol) core structure, and BH 3-protected ortho-phosphanyl phenols, a set of fourteen new C 2-symmetric diphosphine ligands was synthesized. In addition, three related ligands were obtained from ortho-diphenylphosphino-anilines. The fully characterized ligands were then tested in the Pd-catalyzed enantioselective O-allylation of 4-methoxyphenol using crotyl methyl carbonate as a reagent. In addition, a pseudo-intramolecular variant of the reaction, using crotyl 4-methoxyphenyl carbonate as a substrate, was studied. The so-called Trost ligand was used as a reference. Although the Trost ligand (3 mol-%) gave up to 84% ee, one of the new ligands showed higher activity (50% ee with 0.075 mol-%). Copyright

Synthesis and antiproliferative activity of novel methylselenocarbamates

A series of new aliphatic, aromatic and heteroaromatic carbamate derivatives containing a methylseleno moiety were synthesized and evaluated in vitro for their cytotoxic activity against a panel of human cell lines including CCRF-CEM (lymphoblastic leukaemia), K-562 (lymphocytic leukaemia), HT-29 (colon carcinoma), HTB-54 (lung carcinoma), PC-3 (prostate carcinoma), MCF-7 (breast adenocarcinoma), 184B5 (non-malignant, mammary gland derived) and BEAS-2B (non-malignant, derived from bronchial epithelium). Most of the compounds are highly cytotoxic with GI50 values below 10 μM in every tested tumour cell line. Based on its cytotoxic parameters, selectivity index and ADME profile, the biological activity of compound 2, the propyl derivative, was further analysed in CCRF-CEM and HTB-54 cells. Results showed that this compound is able to induce apoptosis in a time- and dose-dependent manner. Involvement of caspases in cell death induction by 2 was detected. Besides, compound 2 was also able to induce cell cycle arrest at G0/G1 in CCRF-CEM cells and at G2/M in HTB-54 cells.

β-type glycosidic bond formation by palladium-catalyzed decarboxylative allylation

The efficient and stereoselective construction of glycosidic linkages is of great significance in carbohydrate chemistry due to the ubiquitous existence of numerous biologically active natural products and saccharides. Although great efforts have been devoted to stereoselective glycosylations in the past few decades, constructing glycosidic bonds with high efficiency and selectivity remains a challenge and continues to be an important area in carbohydrate research. Phenols are widely used as nucleophiles in palladium-catalyzed allylation. In contrast, the possibility of using aliphatic alcohols as nucleophiles is not as thoroughly explored. The modified reaction conditions were then applied to other substrates. Originating from easily prepared carbonates, various glycosides, such as phenolic Oglycosides, thiophenolic S-glycoside, aliphatic O-glycosides, and even disaccharides, were synthesized in good yields by means of a palladium-catalyzed decarboxylative allylation.

Modulation of thermo-transient receptor potential (thermo-TRP) channels by thymol-based compounds

A series of thirty-three thymol, p-cymene-3-carboxylic acid, and 3-amino-p-cymene derivatives was synthesized and tested on TRPA1, TRPM8, and TRPV3 channels. Most of them acted as strong modulators of TRPA1, TRPM8, and TRPV3 channels with EC50 and/or IC50 values distinctly lower than those of thymol and related monoterpenoids. Some of the compounds examined, that is, 3c, 4e, f, 6b, and 8b exhibited an appreciable subtype-selectivity.

NOVEL VINBLASTINE DERIVATIVES, THEIR PREPARATION, USE AND PHARMACEUTICAL COMPOSITIONS COMPRISING THE SAID DERIVATIVES

The invention provides vinblastine derivatives represented by the following formula 1 or their physiologically acceptable salts, their preparation, use and pharmaceutical compositions comprising the said derivatives. The said vinblastine derivatives show inhibiting activities against tumor cell lines and can be used as medicaments for treating malignant tumors.

New N-arachidonoylserotonin analogues with potential "dual" mechanism of action against pain

N-Arachidonoylserotonin (AA-5-HT, 1a) is an inhibitor of fatty acid amide hydrolase (FAAH) that acts also as an antagonist of transient receptor potential vanilloid-type 1 (TRPV1) channels and is analgesic in rodents. We modified the chemical structure of 1a with the aim of developing "hybrid" FAAH/TRPV1 blockers more potent than the parent compound or obtaining analogues with single activity at either of the two targets to study the mechanism of the analgesic action of 1a. Thirty-eight AA-5-HT analogues, containing a serotonin "head" bound to a variety of lipophilic moieties via amide, urea, or carbamate functionalities, were synthesized. Unlike 1a, most of the new compounds possessed activity at only one of the two considered targets. The amides 1b and 1c of α- and γ-linolenic acid, however, showed "hybrid" activity similar to 1a. The carbamate 3f (OMDM106), although unable to antagonize TRPV1 receptors, was the most potent FAAH inhibitor in this study (IC50 = 0.5 μM). Compounds 3f and 1m (OMDM129), which exhibited activity at only FAAH or TRPV1, respectively, were 10-fold less potent than 1a at preventing formalin-induced hyperalgesia in mice.

A facile synthesis of azidoformate via chloroformate

This work synthesized chloroformates by slowly adding alcohols into a suspension of trichloromethyl chloroformate, instead of phosgene, along with activated charcoal in tetrahydrofuran. This chloroformylation yielded chloroformates in near quantitative yield. The subsequent reaction between chloroformates and sodium azide in dry acetone produced azidoformates in a high yield.

Catalyst for decarbonylation reaction

A catalyst composed of an organic phosphorus compound having a trivalent or pentavalent phosphorus atom and at least one carbon-phosphorus bonding or a combination of the organic phosphorus compound and a halogen atom-containing compound is effective for decarbonylation, that is, for releasing carbon monoxide from a compound containing a moiety of --CO--CO--O-- in its molecular structure.

Catalyst for decarbonylation reaction

A catalyst composed of an organic phosphorus compound having a trivalent or pentavalent phosphorus atom and at least one carbon-phosphorus bonding or a combination of the organic phosphorus compound and a halogen atom-containing compound is effective for decarbonylation, that is, for releasing carbon monoxide from a compound containing a moiety of -CO-CO-O- in its molecular structure.