33577-98-9

Usage

Uses

Used in Pharmaceutical Research:
4-(3-Hydroxy-3-methylbut-1-ynyl)benzoic acid methyl ester is used as a key intermediate in pharmaceutical research for the synthesis of novel drug candidates. Its unique structure allows for the exploration of new chemical entities with potential therapeutic benefits.
Used in Organic Synthesis:
In the field of organic synthesis, 4-(3-hydroxy-3-methylbut-1-ynyl)benzoic acid methyl ester serves as a versatile building block for the creation of complex organic molecules. Its reactivity and functional groups enable the formation of a wide range of chemical products.
Used in Drug Development:
4-(3-Hydroxy-3-methylbut-1-ynyl)benzoic acid methyl ester is employed in drug development as a potential active pharmaceutical ingredient. Its properties may contribute to the discovery of new therapeutic agents with improved efficacy and safety profiles.
Used in Medicinal Chemistry:
In medicinal chemistry, 4-(3-hydroxy-3-methylbut-1-ynyl)benzoic acid methyl ester is utilized for the study of structure-activity relationships. Understanding how its structure influences biological activity can guide the design of more effective drugs.
Note: The specific applications and industries for 4-(3-hydroxy-3-methylbut-1-ynyl)benzoic acid methyl ester are not explicitly provided in the materials. The uses listed above are inferred based on its role in organic synthesis and pharmaceutical research. Further research and development are required to identify its precise applications and potential in various industries.

InChI:InChI=1/C13H14O3/c1-13(2,15)9-8-10-4-6-11(7-5-10)12(14)16-3/h4-7,15H,1-3H3

Upstream product

• 619-42-1 4-methoxycarbonylphenyl bromide 
• 115-19-5 2-methyl-but-3-yn-2-ol 
• 619-44-3 methyl 4-iodobenzoate 
• 586-76-5 4-Bromobenzoic acid 

Downstream Products

• 10602-00-3 4-Ethynyl-benzoic acid 
• 3034-86-4 4-ethynylbenzoic acid methyl ester 
• 952527-69-4 4-(3-methoxycarbonyloxy-3-methyl-but-1-ynyl)-benzoic acid methyl ester 
• 952527-22-9 4-(1-methoxycarbonyl-3-methyl-buta-1,2-dienyl)-benzoic acid methyl ester 
• 153114-60-4 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 4-ethynylbenzoate 
• 676443-76-8 4-[3-(2,4-diamino-pyrimidin-5-ylmethyl)-4-methoxy-phenylethynyl]-benzoic acid methyl ester 
• 1260183-80-9 pentafluorophenyl 4-ethynylbenzoate 
• 62480-31-3 4-ethynylbenzoyl chloride 
• 144693-66-3 p-Ethynylbenzoic acid potassium salt 
• 1327278-69-2 3-tert-butyl-5-(4-vinylphenyl)-1,2,4-oxadiazole 
• 1327278-72-7 3-tert-butyl-5-(4-ethylphenyl)-1,2,4-oxadiazole 
• 1327278-70-5 3-tert-butyl-5-(4-ethynylphenyl)-1,2,4-oxadiazole 
• 1355320-80-7 methyl 4-[3,5-bis(hydroxymethyl)phenylethynyl]benzoate 
• 1355320-81-8 4-[3,5-bis(hydroxymethyl)phenylethynyl]benzoic acid 

Relevant academic research and scientific papers

Rhodium-Catalyzed Annulation of Phenacyl Ammonium Salts with Propargylic Alcohols via a Sequential Dual C-H and a C-C Bond Activation: Modular Entry to Diverse Isochromenones

Given their omnipresence in natural products and pharmaceuticals, isochromenone congeners are one of the most privileged scaffolds to synthetic chemists. Disclosed herein is a dual (ortho/meta) C-H and C-C activation of phenacyl ammonium salts (acylammonium as traceless directing group) toward annulation with propargylic alcohols to accomplish rapid access for novel isochromenones by means of rhodium catalysis from readily available starting materials. This operationally simple protocol features broad substrate scope and wide functional group tolerance. Importantly, the protocol circumvents the need of any stoichiometric metal oxidants and proceeds under aerobic conditions.

Rhodium-catalyzed oxidative coupling of benzoic acids with propargyl alcohols: An efficient access to isocoumarins

An efficient protocol of Rh(III)-catalyzed oxidative cyclization of benzoic acids with propargyl alcohols to give substituted isocoumarins under mild conditions was reported. A variety of substrates were applied in this reaction in yields up to 89%.

RET INHIBITORS, PHARMACEUTICAL COMPOSITIONS AND USES THEREOF

Provided herein are a RET inhibitor, a pharmaceutical composition thereof and uses thereof. In particular, provided is a compound having Formula (I) or a stereoisomer, a geometric isomer, a tautomer, an N-oxide, a solvate, a metabolite, a pharmaceutically acceptable salt or a prodrug thereof. Provided is a pharmaceutical composition comprising the compound, and uses of the compound and pharmaceutical composition thereof for the preparation of a medicament, in particular for treatment and prevention of RET-related diseases and conditions, including cancer, irritable bowel syndrome, and/or pain associated with irritable bowel syndrome.

Palladium(II)/Lewis acid cocatalyzed oxidative annulation of 2-alkenylanilines and propargylic esters: An access to benzo[ b]azepines

An attractive approach to valuable yet synthetically challenging benzo[b]azepines was established via palladium(II)/Lewis acid cocatalyzed oxidative [5 + 2] annulation of readily available 2-alkenylanilines and propargylic esters. The protocol features mild reaction conditions and good functional group tolerance, constituting an array of benzo[b]azepines in yields of 30-75%.

Hydrotalcite-supported palladium nanoparticles as catalysts for the hydroarylation of carbon-carbon multiple bonds

Palladium nanoparticles supported on Mg/Ca hydrotalcites catalyze the hydroarylation reaction of different alkynes and alkenes with aryl iodides under air in MeCN. The reaction of tertiary propargylic alcohols (1) with aryl iodides (2) yields, stereoselectively, γ,γ-diarylallylic alcohols (3) in moderate to high yields and high selectivity. Also, the HT/Pd hydroarylation reaction with aryl iodides was attempted on norbornene and α,β-unsaturated ketones affording, respectively, exo-aryl bicyclo[2.2.1]heptanes and β-aryl ketones in moderate to high yields. All the reactions described benefit from using a heterogeneous catalyst with evident advantages in terms of reaction purification and recyclability of the catalyst.

Sonogashira-Hagihara and Buchwald-Hartwig cross-coupling reactions with sydnone and sydnone imine derived catalysts

Seven different palladium complexes of sydnones and sydnone imines and a co-catalyst system consisting of lithium sydnone-4-carboxylate and Pd(PPh3)4 catalyzed Sonogashira-Hagihara reactions between (hetero)- aromatic bromides and 2-methylbut-3-yn-2-ol (52 examples, up to 100% yield). The co-catalyst system and a sydnone Pd complex were also tested in Buchwald-Hartwig reactions (9 examples, up to 100% yield). (Equation Presented).

Chemistry and spectroscopy of cross-conjugated and pseudo-cross-conjugated quinolinium-ethynyl-benzoate mesomeric betaines

The three isomers 1-methylquinolinium-2-, 3-, and 4-ethynyl(phenyl-4-carboxylates) belong to two distinct types of heterocyclic mesomeric betaines. The quinolinium substituted in position 3 is a cross-conjugated mesomeric betaine (CCMB), whereas the quinolinium derivatives substituted in positions 2 and 4 are members of the class of pseudo-cross-conjugated mesomeric betaines (PCCMBs). While the charges are strictly separated within the common π-electron system of the CCMB according to the canonical formulae, the charges are effectively but not exclusively delocalized in the PCCMBs because cumulenoid resonance forms including electron sextet structures without external octet stabilization can be formed in accordance with the definition of PCCMBs. As a consequence, despite being closely related structures, the three isomers differ in their chemical and spectroscopic behaviors. Thus, on trying to hydrolyze the ester group of the methyl quinolinium-2-ethynyl-benzoate into the corresponding acid by subsequent treatment with sodium hydroxide in methanol and aqueous hydrochloric acid at pH 3, the acetal methyl 1,1-dimethoxy-2-(quinolinium-ylidene)ethyl]benzoate and the corresponding β-enamino carbonyl compound were formed, respectively. The corresponding acids of the 2- and 4-substituted quinolinium-ethynyl-benzoates were obtained by a modified procedure. On deprotonation, the resulting cross-conjugated quinolinium-3-ethynyl-benzoate betaine proved to be stable, whereas the corresponding pseudo-cross-conjugated quinolinium-2- and -4-ethynyl-benzoate betaines decomposed. Frontier orbital profiles were calculated, and IR and Raman spectra of the starting materials were measured and calculated to analyze the differences of CCMBs and PCCMBs of mesomeric betaines possessing triple bonds. A higher contribution of the cumulenoid resonance forms to the overall structure of the PCCMBs was determined.

Benzophenanthrene benzoyloxy benzene bridged perylene bisimide diester synthetic method

The invention provides a benzophenanthrene benzoyloxy benzene bridged perylene bisimide diester synthetic method. A synthesis route is characterized in that 1) p-acetenyl benzoic acid is synthesized; monohydroxy pentahexyloxy benzophenanthrene is generated; a benzophenanthrene derivative containing terminal alkyne is finally prepared; 2) N-(4-iodophenyl)perylene imine dioctyl phthalate diester is generated; and 3) an intermediate obtained by the above two parts, and a benzophenanthrene benzoyloxy benzene bridged perylene bisimide diester binary compound is obtained through a reaction by a Sonogashira cross-coupling reaction. The benzophenanthrene and its derivative are most widely discotic liquid crystal material in the prior art, have good photoelectric property, and can easily form a cylindrical liquid crystalline phase, a perylene imide derivative has strong electronic capacity, has high electronic affinity, has strong absorption capacity at a visible light zone, and is an excellent n-type organic semiconductor material. The discotic liquid crystal binary compound with an electron donor (D)-bridge (B)-acceptor (A) structure is designed and synthesized, and can be used for molecule devices of an organic photovoltaic material, a liquid crystal material, an organic solar energy cell, and an organic light-emitting diode.

Synthesizing method of benzophenanthrene benzoyloxy alkynylphenyl alkynylphenyl bridged perylene mono-imide dihexyl ester

The invention aims at providing a synthesizing method of benzophenanthrene benzoyloxy alkyne benzyne benzene bridged perylene mono-imide dihexyl ester. A synthesizing path of the synthesizing comprises the first part of synthesizing iodine-containing phenyl ethynyl benzoyloxy penta-hexyloxy benzophenanthrene, the second part of utilizing 3,4,9,10-perylene tetracarboxylic acid anhydride as a raw material and synthesizing alkyne-containing phenyl perylene bisimide diester derivative and the third part of synthesizing intermediates obtained through the first part and the second part into benzophenanthrene oxycarbonyl phenylalkynylphenyl alkynylphenyl bridged perylene mono-imide dihexyl ester binary compound through Sonogashira cross coupling reaction. Benzophenanthrene and derivative of the benzophenanthrene are disc-shaped liquid crystal materials which are most extensively utilized currently, and perylene bisimide derivative is an excellent n type organic semiconductor material. The synthesizing method disclosed by the invention designs and synthesizes disc-shaped liquid crystal binary compound containing an electron donor-bridge-receptor structure, and the compound can be applied to molecular devices of organic solar cells, organic light emitting diodes and the like.

Synthesis method of triphenylene benzoyloxy alkynyl biphenyl alkynyl benzene bridged perylene monoimine dihexyl ester

The invention aims at providing a synthesis method of triphenylene oxycarbonyl phenylacetylenic biphenyl alkyne benzene bridged perylene monoimine dihexyl ester. The synthesis method comprises the synthesis routes: firstly, synthesizing iodine-containing biphenylyl acetenyl benzoyloxy pentaoctoxytriphenylene; secondly, synthesizing an alkyne-containing phenyl perylene imide diester derivative by taking perylene tetracarboxylic anhydride as a raw material; and thirdly, carrying out Sonogashira cross-coupling reaction on an intermediate obtained by the two steps to synthesize a triphenylene oxycarbonyl phenylacetylenic biphenyl alkyne benzene bridged perylene monoimine dihexyl ester binary compound. Triphenylene and a derivative thereof are discoid liquid crystal materials most extensively applied at present, while a perylene imide derivative is a favorable N-type organic semiconductor material. The invention designs and synthesizes a discoid liquid crystal binary compound with an electron donor-bridge-receptor structure, and the compound can be applied to molecular devices such as organic solar cells and organic light-emitting diodes.