8-benzoxy-5-(R)-oxiranyl-1H-quinolin-2-one, CAS No. 173140-90-4

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173140-90-4

Catalog No. EBD251084

CAS 173140-90-4

Name 8-benzoxy-5-(R)-oxiranyl-1H-quinolin-2-one

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Basic Information

Synonyms: 5-(2R)-2-Oxiranyl-8-benzyloxy-2(1H)-quinolinone (R)-8-(Benzyloxy)-5-(oxiran-2-yl)quinolin-2(1H)-one 2(1H)-Quinolinone,5-(2R)-oxiranyl-8-(phenylmethoxy)- 8-benzoxy-5-(R)-oxiranyl-1H-quinolin-2-one 8-(benzyloxy)-5-[(2R)-oxiran-2-yl]quinolin-2(1H)-one 8-(phenylmethoxy)-5-(R)-oxiranyl-(1H)-quinolin-2-one 8-(phenylmethoxy)-5-(R)-oxiranyl-1H-quinolin-2-one 8-phenylmethoxy-5-(R)-oxiranyl-1H-quinolin-2-one R-8-benzyloxy-5-oxiranyl-1H-quinolin-2-one (R)-8-benzyloxy-5-oxiranylcarbostyril

Molecular Formula: C18H15NO3

Molecular Weight: 293.32

Categories: Medicinal Chemistry > Pharmaceutical Intermediates > Heterocyclic Intermediates Medicinal Chemistry > APIs and Their Salts > Antineoplastic Agents

Product Description:

5-((2R)-2-Oxiranyl)-8-(benzyloxy)-2(1H)-quinolinone is a chiral, heterocyclic organic compound featuring a quinolinone core substituted with a benzyloxy group and an epoxide (oxirane) ring. The presence of the epoxide moiety is a key structural feature, making it a reactive electrophilic intermediate. This compound is primarily documented as a crucial synthetic intermediate in the preparation of potent and selective inhibitors of the epidermal growth factor receptor (EGFR) tyrosine kinase. Specifically, it serves as a key chiral building block in the synthesis pathway for advanced anti-cancer agents, such as Erlotinib (Tarceva®) and related analogues. These drugs are used in the treatment of non-small cell lung cancer (NSCLC) and pancreatic cancer. The compound's reactivity stems from the strained three-membered epoxide ring, which can undergo ring-opening reactions with nucleophiles, enabling the construction of more complex molecular architectures essential for drug activity. Handling requires appropriate safety precautions due to the potential reactivity of the epoxide group.

Physical Properties