200132-54-3 Usage
Description
O-Allyl-N-(9-anthracenylmethyl)cinchonidinium bromide is a cinchona-based chiral phase-transfer catalyst (PTC) derived from N-(9-anthracenylmethyl)cinchonindinium chloride. It is characterized by its ability to facilitate asymmetric synthesis reactions, making it a valuable compound in the field of organic chemistry.
Uses
Used in Asymmetric Synthesis:
O-Allyl-N-(9-anthracenylmethyl)cinchonidinium bromide is used as a catalyst for the asymmetric alkylation of tert-butyl glycinate-benzophenone Schiff base with different arylmethyl bromides in a micellar medium. This application is significant because it allows for the selective formation of chiral molecules, which are crucial in the pharmaceutical industry for the development of enantiomerically pure drugs.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, O-Allyl-N-(9-anthracenylmethyl)cinchonidinium bromide is used as a catalyst for the synthesis of chiral compounds. The ability to produce enantiomerically pure drugs is essential, as the different enantiomers of a drug can have vastly different biological activities and effects. This catalyst aids in the development of more effective and safer medications by ensuring the correct chirality of the synthesized compounds.
Used in Chemical Research:
O-Allyl-N-(9-anthracenylmethyl)cinchonidinium bromide is also utilized in chemical research for studying the mechanisms and optimization of asymmetric synthesis reactions. Its use in this context contributes to the advancement of knowledge in the field of organic chemistry and the development of new synthetic methods and techniques.
Check Digit Verification of cas no
The CAS Registry Mumber 200132-54-3 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 2,0,0,1,3 and 2 respectively; the second part has 2 digits, 5 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 200132-54:
(8*2)+(7*0)+(6*0)+(5*1)+(4*3)+(3*2)+(2*5)+(1*4)=53
53 % 10 = 3
So 200132-54-3 is a valid CAS Registry Number.
InChI:InChI=1/C37H37N2O.BrH/c1-3-21-40-37(33-17-19-38-35-16-10-9-15-32(33)35)36-23-27-18-20-39(36,24-26(27)4-2)25-34-30-13-7-5-11-28(30)22-29-12-6-8-14-31(29)34;/h3-17,19,22,26-27,36-37H,1-2,18,20-21,23-25H2;1H/q+1;/p-1/t26-,27-,36-,37+,39?;/m0./s1
200132-54-3Relevant articles and documents
Bioactive indanes: Proof of concept study for enantioselective synthetic routes to ph46a, a new potential anti-inflammatory agent
Zhang, Tao,Scalabrino, Gaia,Frankish, Neil,Sheridan, Helen
, (2018/07/10)
PH46A is a single enantiomer and a member of the 1,2-indane dimer family. It has two contiguous stereogenic centers with S,S configurations, one of which being a quaternary center, which has been developed as a clinical candidate for the treatment of inflammatory and autoimmune conditions. The current synthetic route to PH46A involves the generation of an unwanted enantiomer (R,R)-7, thus reducing the final yield significantly. Therefore, we have investigated potential alternatives to improve the efficiency of this synthesis. The first phase of the study has demonstrated proof of principle for a chiral alkylation of ketone 3 using phase-transfer catalysis, providing a key intermediate ketone (S)-4. The parent alkaloids required for the synthesis of PH46A, quinine or cinchonidine, have also been identified. Promising enantiomeric excesses of up to 50% have been achieved to date, and the use of an alternative substrate, unsaturated ketone 9, has also opened up further avenues for optimisation in future studies. The second part of the study involved preliminary screening the effects of a panel of hydrolase enzymes on (rac)-4 in order to identify a potential chemo-enzymatic route to optimise the introduction of chirality into PH46A at early stage of the synthesis. The hydrolase module has also yielded positive results; enzyme AH-46 with MtBE providing a selectivity factor of 8.4 with enantiomeric excess of 77%. Overall, positive results were obtained in this proof of concept study described herein. It is believed that conditions of both chiral PTC alkylation and biocatalytic hydrolysis could be optimised to further enhance the selectivity and improve the overall yield. This work is currently ongoing.
