158299-05-9

Basic information

• Product Name: 3-(2-Bromo-1-oxopropyl)-spiro[2H-1,3-benzoxazine-2,1'-cyclohexan]-4(3H)-one
• Synonyms: 3-(2-BROMO-1-OXOPROPYL)-SPIRO[2H-1,3-BENZOXAZINE-2,1'-CYCLOHEXAN]-4(3H)-ONE;BPSBC;BR-Comp;3-isobutyrylspiro[benzo[e][1,3]oxazine-2,1'-cyclohexan]-4(3H)-one;3-(2-Bromo-1-oxopropyl)-spiro[2H-1,3-benzoxazine-2,1'-cyclohexan]-4(3H)-ketone;3-(2-Bromo-1-oxoprop;3-(2-Bromo-1-oxopropyl)-spiro[2H-1,3-benzoxazine-2,1'-cyclohexan]-4(3H)-one (BPSBC);3-(2-broMopropionyl)spiro[2H-1,3-benzoxazine-2,1'-cyclohexane]-4(3H)-one
• CAS NO: 158299-05-9
• Molecular Formula: C₁₆H₁₈BrNO₃
• Molecular Weight: 352.22
• EINECS: 1806241-263-5
• Mol File: 158299-05-9.mol

Chemical Properties

• Melting Point: 74-76 °C
• Boiling Point: 485 °C at 760 mmHg
• Flash Point: 247.1 °C
• Appearance: /
• Density: 1.48 g/cm³
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: -2.33±0.20(Predicted)
• CAS DataBase Reference: 3-(2-Bromo-1-oxopropyl)-spiro[2H-1,3-benzoxazine-2,1'-cyclohexan]-4(3H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(2-Bromo-1-oxopropyl)-spiro[2H-1,3-benzoxazine-2,1'-cyclohexan]-4(3H)-one(158299-05-9)
• EPA Substance Registry System: 3-(2-Bromo-1-oxopropyl)-spiro[2H-1,3-benzoxazine-2,1'-cyclohexan]-4(3H)-one(158299-05-9)

Safety Data

• Hazardous Substances Data: 158299-05-9(Hazardous Substances Data)

Usage

Application

A useful research chemical compound.

storage

Store the container tightly closed in a dry, cool and well-ventilated place. Store apart from foodstuff containers or incompatible materials.

Upstream product

• 40033-95-2 Spiro-<2,3-dihydro-4H-1,3-benzoxazine-1,2'-cyclohexan>-4-one 
• 563-76-8 α-bromopropionyl bromide 
• 108-94-1 cyclohexanone 
• 65-45-2 salicylamide 

Downstream Products

• 40033-95-2 Spiro-<2,3-dihydro-4H-1,3-benzoxazine-1,2'-cyclohexan>-4-one 
• 74632-85-2 trans-3-methyl-1-phenyl-4-[(E)-2-phenylethenyl]azetidin-2-one 
• 17324-17-3 trans-3-methyl-1,4-diphenylazetidin-2-one 

Relevant articles and documents

Preparation method of 3-(2-chloro-1-oxopropyl)-spiro[2H-1,3-benzoxazine-2,1'-cyclohexan]-4(3H)-one as meropenem intermediate

The invention provides a preparation method of 3-(2-chloro-1-oxopropyl)-spiro[2H-1,3-benzoxazine-2,1'-cyclohexan]-4(3H)-one as a meropenem intermediate. According to the preparation method, alpha-chloropropionyl chloride with lower reaction activity is adopted and cooperates with specific raw materials to play a role together, so that the reaction yield is greatly increased instead of being reduced; meanwhile, due to the lower activity of alpha-chloropropionyl chloride, fewer side reactions participate in the reaction, an obtained product contains fewer impurities, and 3-(2-chloro-1-oxopropyl)-spiro[2H-1,3-benzoxazine-2,1'-cyclohexan]-4(3H)-one with higher yield and purity is obtained and can replace 3-(2-bromo-1-oxopropyl)-spiro[2H-1,3-benzoxazine-2,1'-cyclohexan]-4(3H)-one for preparing meropenem. Besides, a synthetic process of 3-(2-chloro-1-oxopropyl)-spiro[2H-1,3-benzoxazine-2,1'-cyclohexan]-4(3H)-one requires no magnetic solid base catalysts, so that the reaction conditions are safer, the reaction path is simple, aftertreatment is convenient, the raw materials and the catalyst are inexpensive and available, and the preparation method is safe, environment-friendly, lower in preparation cost and more suitable for industrial production.

Process development on (3S,4S)-[(R)-1′-((tert-butyldimethylsilyl)oxy)ethyl]-4-[(R)-1- carboxyethyl]-2-azetidinone 1-β-methylcarbapenem key intermediate

The process for the stereoselective synthesis of the 1-β-methylcarbapenem key intermediate 2 via the Reformatsky-type reaction employing a dihydro-oxazinone derivative has been developed for large-scale production. The most difficult problem involved in the development was the exothermic nature of the reaction. Change of acidification order avoided the heat release in the hydrolysis of 5 to 2.

2-Substituted 2,3-dihydro-4H-1,3-benzoxazin-4-ones: Novel auxiliaries for stereoselective synthesis of 1-β-methylcarbapenems

The dihydrobenzoxazone 9e, which is easily prepared from salicylamide 11 and cyclohexanone, serves as an efficient auxiliary in the synthesis of the 1-β-methylcarbapenem key intermediate 10. The stereocontrolled Reformatsky-type reactions of the acetoxyazetidinone 2 with the carboximides 6 gave the intermediates 7 with high diastereoselectivities in high chemical yields. The auxiliary 9e also acts as a good leaving guoup in the TMSCl-promoted Dieckmann-type cyclization leading to a 1-β-methylcarbapenem skeleton. By using this auxiliary, 10 was synthesized in 58% overall yield and four steps from 2.

Efficient synthesis of 1β-methylcarbapenems based on the counter-attack strategy

A seven-step efficient synthesis of 1β-methylcarbapenems 1 from the acetoxyazetidinone 6 is described. The Reformatsky reaction of 3-(2-bromopropionyl)-1,3-benzoxazinone 7 with compound 6 gave an adduct 8 in 96% yield with high β-selectivity (β:α = 92:8). Compound 8 was transformed in three steps into the side-chain thiol esters 12a-e in good yields. The chlorotrimethylsilane-mediated Dieckmann-type cyclisation of thioesters 12b-e followed by counter-attack of the liberated thiolate anion 18 yielded the C-2 alkylthio- or arylthio-substituted 1β-methylcarbapenems 19b-e in a one-pot procedure. The synthesis of 1β-methylcarbapenems 1 was demonstrated by a simple cleavage of the silyl ether and allyl ester of compound 19b to afford target compound 1b in high yield.

Azetidinone compound and process for preparation thereof

There is disclosed an azetidinone compound of the formula [I]: STR1 wherein Ring B is a benzene ring which may have substituent(s), R1 is a hydroxy-substituted lower alkyl group which may have substituent(s), X is oxygen atom and the like, Y is oxygen atom and the like, and Z is a methylene group which may have substituent(s), which is useful as a synthetic intermediate of the 1β-methylcarbapenem-type antibacterial agent.