160678-57-9

Basic information

• Product Name: (R)-3-(4-bromophenyl)cyclopentan-1-one
• Synonyms: (R)-3-(4-bromophenyl)cyclopentan-1-one
• CAS NO: 160678-57-9
• Molecular Weight: 239.112
• Mol File: 160678-57-9.mol
• Article Data: 17

Chemical Properties

• CAS DataBase Reference: (R)-3-(4-bromophenyl)cyclopentan-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-3-(4-bromophenyl)cyclopentan-1-one(160678-57-9)
• EPA Substance Registry System: (R)-3-(4-bromophenyl)cyclopentan-1-one(160678-57-9)

Safety Data

• Hazardous Substances Data: 160678-57-9(Hazardous Substances Data)

Upstream product

• 930-30-3 cyclopent-2-enone 
• 5467-74-3 4-Bromophenylboronic acid 
• 108-86-1 bromobenzene 
• 14320-38-8 cyclopent-3-enol 
• 673-40-5 4-bromobenzenediazonium tetrafluoroborate 

Downstream Products

• 1476776-44-9 (S)-5-(4-bromophenyl)piperidin-2-one 
• 1335523-82-4 4-(3S-piperidine-3-yl)bromobenzene 
• 1036070-23-1 (1R,3R)-methyl 1-amino-3-(4-bromophenyl)cyclopentanecarboxylate 
• 1669432-63-6 2-(4-((5R,7R)-2-oxo-3-oxa-1-azaspiro[4.4]nonan-7-yl)phenyl)acetic acid 
• 1622180-60-2 tert-butyl 2-(4-((5R,7R)-2-oxo-3-oxa-1-azaspiro[4.4]nonan-7-yl)phenyl)acetate 
• 1240464-41-8 ((1R,3R)-1-amino-3-(4-bromophenyl)cyclopentyl)methanol 
• 1622180-54-4 (5R,7R)-7-(4-bromophenyl)-3-oxa-1-azaspiro[4.4]nonan-2-one 
• 1622180-52-2 (3R)-1-amino-3-(4-bromophenyl)cyclopentanecarboxylic acid 
• 1211472-99-9 N-{4-[(1R,3S)-3-{[(1R)-1-(Naphthalen-1-yl)ethyl]amino}cyclopentyl]benzoyl}glycine ethyl ester 
• 1211472-97-7 4-[(1R,3S)-3-{[(1R)-1-(naphthalen-1-yl)ethyl]amino}cyclopentyl]benzoic acid hydrochloride 
• 1211472-94-4 4-[(1R,3S)-3-{[(1R)-1-(Naphthalen-1-yl)ethyl]amino}cyclopentyl]benzoic acid ethyl ester 
• 1211471-80-5 N-{4-[(1R,3S)-3-{[(1R)-1-(Naphthalen-1-yl)ethyl]amino}cyclopentyl]benzoyl}glycine hydrochloride 
• 1211472-82-0 (1S,3R)-3-(4-bromophenyl)-N-[(1R)-1-(naphthalen-1-yl)ethyl]cyclopentanamine 

Relevant articles and documents

Fine-Tuning the Bicyclo[3.3.1]nona-2,6-diene Ligands: Second Generation 4,8-Substituted Dienes for Rh-Catalyzed Asymmetric 1,4-Addition Reactions

Design and synthesis of the second generation C2-symmetric 4,8-endo,endo-bis(alkoxy) bicyclo[3.3.1]nona-2,6-diene ligands possessing additional 4,8-exo,exo substituents is reported. The 4,8-exo,exo groups provide a further element for fine-tuning of the ligand structure by enforcing conformational rigidity of the 4,8-endo,endo side chains. Such tetrasubstituted bicyclo[3.3.1]nona-2,6-dienes were employed as steering ligands in the rhodium-catalyzed arylation of cyclic enones with arylboronic acids, providing the corresponding 1,4-addition products in good to excellent yields (69–99 %) and enantioselectivities up to 99 % ee.

Preparation method of niraparib intermediate 4-(3S-piperidine-3-yl)bromobenzene

The invention discloses a preparation method of niraparib intermediate 4-(3S-piperidine-3-yl)bromobenzene. The preparation method is characterized by comprising steps as follows: 1) a compound shown in a formula I and hydroxylammonium chloride are subjected to a contact reaction to produce a compound shown in a formula II; 2) the compound shown in the formula II and phenyl dichlorophosphate are subjected to a catalytic reaction to produce a compound shown in a formula III; 3) the compound shown in the formula III is subjected to a reduction reaction to produce niraparib intermediate 4-(3S-piperidine-3-yl)bromobenzene shown in a formula X, and the specific reaction process is shown in the specification. A new synthesis way is provided for the niraparib intermediate 4-(3S-piperidine-3-yl)bromobenzene, metal catalysts, expensive transaminase and the like are not used in the reaction process, the production cost is low, and the product has the good yield and stereoselectivity.

4,8-disubstituted bicyclo[3.3.1]nona-2,6-dienes as chiral ligands for rh-catalyzed asymmetric 1,4-addition reactions

C2-symmetric chiral diene ligands based on 4,8-endo,endo-disubstituted bicyclo[3.3.1]nona-2,6-diene framework have been designed and synthesized. The rhodium complexes of the dienes, which were obtained in a few straightforward steps from enantiomerically pure bicyclo[3.3.1]nonane-2,6-dione, exhibited excellent catalytic activity and high enantioselectivity (up to 96% ee) in the conjugate addition reaction of arylboronic acids to cyclic enones under mild reaction conditions with high atom efficiency. Chiral C2-symmetric 4,8-endo,endo-disubstituted bicyclo[3.3.1]nona-2,6-diene ligands were synthesized from easily available bicyclo[3.3.1]nonane-2,6-dione and utilized in the asymmetric 1,4-addition reaction of arylboronic acids to cyclic enones. The catalyst prepared in situ from ligand 4b and [RhCl(C2H4)2]2 exhibited excellent catalytic activity and high enantioselectivity (up to 96% ee) under mild reaction conditions with high atom efficiency.