33388-19-1

Usage

Uses

Used in Pharmaceutical and Agrochemical Synthesis:
2(3H)-Benzoxazolone,3-(1-oxopropyl)is utilized as a key intermediate in the synthesis of various pharmaceuticals and agrochemicals. Its unique structure and reactivity make it a valuable component in the development of new drugs and pesticides, contributing to advancements in healthcare and agriculture.
Used in Dyes and Pigments Production:
2(3H)-Benzoxazolone,3-(1-oxopropyl)is employed in the production of dyes and pigments, where its chemical properties allow for the creation of a wide range of colors and hues. Its use in this industry contributes to the development of new and improved colorants for various applications, including textiles, plastics, and printing inks.
Used in Material Science:
2(3H)-Benzoxazolone,3-(1-oxopropyl)has potential applications in the field of material science, where its properties can be harnessed to develop new materials with unique characteristics. Its use in this field can lead to innovations in areas such as polymers, coatings, and advanced materials for various industries.
Used as a Building Block for Organic Synthesis:
Due to its versatile nature, 2(3H)-Benzoxazolone,3-(1-oxopropyl)serves as a building block for organic synthesis, enabling the creation of a variety of complex organic compounds. Its use in this capacity can facilitate the development of new chemical entities with potential applications in various fields, including pharmaceuticals, agrochemicals, and materials science.

InChI:InChI=1/C10H9NO3/c1-2-9(12)11-7-5-3-4-6-8(7)14-10(11)13/h3-6H,2H2,1H3

Upstream product

• 59-49-4 2-Benzoxazolinone 
• 123-62-6 propionic acid anhydride 
• 79-03-8 propionyl chloride 

Downstream Products

• 54903-11-6 6-propanoyl-3H-1,3-benzoxazol-2-one 
• 1356851-23-4 (S)-3-(2-(3-((tert-butyldiphenylsilyl)oxy)propyl)-4-(trimethylsilyl)pent-4-enoyl)benzo[d]oxazol-2(3H)-one 
• 1356851-22-3 (S)-3-(2-(3-((tert-butyldiphenylsilyl)oxy)propyl)-4-methylpent-4-enoyl)benzo[d]oxazol-2(3H)-one 
• 1356851-19-8 (R,E)-3-(2-cyclohexyl-5-phenylpent-4-enoyl)benzo[d]oxazol-2(3H)-one 
• 1356851-18-7 (R)-3-(2-cyclohexylpent-4-enoyl)benzo[d]oxazol-2(3H)-one 
• 1356851-17-6 (R)-3-(2-benzyl-4-methylpent-4-enoyl)benzo[d]oxazol-2(3H)-one 
• 1356851-34-7 3-(2-cyclohexylacetyl)benzo[d]oxazol-2(3H)-one 
• 1356851-15-4 (S,E)-3-(5-phenyl-2-propylpent-4-enoyl)benzo[d]oxazol-2(3H)-one 
• 1356851-11-0 (S,E)-3-(2-methyl-5-phenylpent-4-enoyl)benzo[d]oxazol-2(3H)-one 
• 1356851-10-9 3-((2S)-2-(cyclohex-2-en-1-yl)propanoyl)benzo[d]oxazol-2(3H)-one 
• 1356851-04-1 (Z)-5-((tert-butyldiphenylsilyl)oxy)-1-(2-oxobenzo[d]oxazol-3(2H)-yl)pent-1-en-1-yl (2-(trimethylsilyl)allyl) carbonate 
• 1356851-03-0 (Z)-5-((tert-butyldiphenylsilyl)oxy)-1-(2-oxobenzo[d]oxazol-3(2H)-yl)pent-1-en-1-yl (2-methylallyl) carbonate 
• 1356851-00-7 cinnamyl ((Z)-2-cyclohexyl-1-(2-oxobenzo[d]oxazol-3(2H)-yl)vinyl) carbonate 
• 1356850-99-1 (Z)-allyl (2-cyclohexyl-1-(2-oxobenzo[d]oxazol-3(2H)-yl)vinyl) carbonate 

Relevant academic research and scientific papers

Producing 3-hydroxycarboxylic acid and ketone using polyketide synthases

The present invention provides for a polyketide synthase (PKS) capable of synthesizing a 3-hydroxycarboxylic acid or ketone. The present invention also provides for a host cell comprising the PKS and when cultured produces the 3-hydroxycarboxylic acid or ketone.

BENZOXAZOLONE DERIVATIVES AS ACID CERAMIDASE INHIBITORS, AND THEIR USE AS MEDICAMENTS

The present invention relates to benzoxazolone derivatives as acid ceramidase inhibitors, pharmaceutical compositions containing these inhibitors and methods of inhibiting acid ceramidase for the treatment of disorders in which modulation of the levels of ceramide is clinically relevant. The invention also provides benzoxazolone derivatives for use as a medicament in the treatment of cancer, inflammation, pain, inflammatory pain or pulmonary diseases.

Palladium-catalyzed allylic alkylation of carboxylic acid derivatives: N-acyloxazolinones as ester enolate equivalents

Triple A: A general asymmetric allylic alkylation of ester enolate equivalents at the carboxylic acid oxidation state is reported. N-Acylbenzoxazolinone-derived enol carbonates were synthesized and employed in the palladium-catalyzed alkylation reaction. The imide products were readily converted into a series of carboxylic acid derivatives without loss of enantiopurity.

Design and synthesis of 3-acyl-2(3H)-benzoxazolone and 3-acyl-2(3H)- benzothiazolone derivatives

A simpler and efficient "green" method using solid sodium hydroxide in a solvent mixture of acetone/water was found to catalyze N-acylation of 2(3H)-benzoxazolones and 2(3H)-benzothiazolones for facile and rapid synthesis of N-acyl derivatives in excellent yields. This method was applied to the synthesis of a series of 132 compounds employing a variety of acyl chlorides. Graphical abstract: [Figure not available: see fulltext.]

Electrogenerated N-heterocyclic carbenes: N-functionalization of benzoxazolones

A simple electrochemical procedure for the N-acylation and N-alkylation of benzoxazol-2(3H)-ones has been set up via electrolysis of an ionic liquid containing a benzoxazolone followed by addition of saturated or unsaturated anhydrides or alkyl halides. The electrochemically induced N-functionalization of benzoxazol-2(3H)-ones works very well in all tested ionic liquids, avoiding the use of volatile organic solvents. The N-acyl and N-alkyl derivatives of benzoxazol-2(3H)-ones were isolated in good to excellent yields; moreover, the ionic liquid has been reused fivefold maintaining the high yield of the products.

N-Acyl-2-benzoxazolinones in titanium-mediated aldol reactions

N-Acyl-2-benzoxazolinones readily form trichlorotitanium enolates that react rapidly with aldehydes to provide crystalline syn-aldol adducts in high yield. The resulting products are simply converted to amides, esters, and thioesters. A simple, economical

Racemic thioesters for production of polyketides

Facile methods for preparing diketide and triketide thioesters are disclosed. The resulting thioesters may be used as intermediates in the synthesis of desired polyketides, and may contain functional groups which ultimately reside in side chains on the resulting polyketide and thus can be used further to manipulate the polyketide so as form derivatives. The polyketides produced may also be tailored by glycosylation, hydroxylation and the like. New polyketides and their derivatives and tailored forms are thereby produced.

'Fries like' rearrangement: A novel and efficient method for the synthesis of 6-acyl-2(3H)-benzoxazolones and 6-acyl-2(3H)-benzothiazolones

6-Acyl-2(3H)-benzoxazolone and 6-acyl-2(3H)-benzothiazolone derivatives have particularly interesting anti-inflammatory, antiepileptic, analgesic and antiviral properties. In this study, we report an original method of acylation on the 6-position of 2(3H)-banzoxazolone and 2(3H)benzothiazolone which consists in a two-step procedure involving migration of the acyl group from the N-position to the 6-position of the hetexocycle, at 165 °C and catalyzed by AlCl3. This new procedure was found to be more efficient with regard to the consumption of AICI3 and the yield (76-90%) than other acylation methods previously described.

Synthesis and anticonvulsant activity of 2(3H)-benzoxazolone and 2(3H)- benzothiazolone derivatives

A series of 2(3H)-benzoxazolone and 2(3H)-benzothiazolone derivatives were synthesized and evaluated for anticonvulsant activity. The compounds were assayed, intraperitoneally in mice and per os in rats, against seizures induced by maximal electroshock (MES) and pentylene-tetrazole (scMet). Neurologic deficity was evaluated by the rotarod test. The compounds were prepared to determine the relationship between the 2(3H)-benzoxazolone and 2(3H)-benzothiazolone derivatives' structures and anticonvulsant activity. Several of these compounds showed significant anticonvulsant activity. Compounds 43 and 45 were the most active of the series against MES-induced seizures with ED50 values of 8.7 and 7.6 mg/kg, respectively. Compound 45 displayed good protection against MES-induced seizures and low toxicity in rats with an oral ED50 of 18.6 mg/kg and a protective index (PI = TD50/ED50) of 1 receptors with nanomolar affinities.