18385-69-8

Basic information

• Product Name: 7-Methyl-2,3-dihydro-4H-1-benzopyran-4-one
• Synonyms: 2,3-Dihydro-7-methyl-4H-1-benzopyran-4-one;7-Methyl-2,3-dihydro-4H-1-benzopyran-4-one;7-Methyl-2,3-dihydrochroMen-4-one
• CAS NO: 18385-69-8
• Molecular Formula: C₁₀H₁₀O₂
• Molecular Weight: 162.19
• Mol File: 18385-69-8.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 138 °C(Press: 13 Torr)
• Appearance: /
• Density: 1.1576 g/cm3(Temp: 21 °C)
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 7-Methyl-2,3-dihydro-4H-1-benzopyran-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 7-Methyl-2,3-dihydro-4H-1-benzopyran-4-one(18385-69-8)
• EPA Substance Registry System: 7-Methyl-2,3-dihydro-4H-1-benzopyran-4-one(18385-69-8)

Safety Data

• Hazardous Substances Data: 18385-69-8(Hazardous Substances Data)

Usage

Description

7-Methyl-2,3-dihydro-4H-1-benzopyran-4-one, also known as 7-Methylchroman-4-one, is an organic compound belonging to the chroman-4-one family. It is characterized by the presence of a methyl group at the 7th position and a 2,3-dihydro-4H-1-benzopyran-4-one structure. 7-Methyl-2,3-dihydro-4H-1-benzopyran-4-one serves as a key intermediate in the synthesis of various pharmaceutical agents and has potential applications in the development of therapeutics.

Uses

Used in Pharmaceutical Industry:
7-Methyl-2,3-dihydro-4H-1-benzopyran-4-one is used as a key intermediate in the preparation of N-substituted 2-oxo-6-(trifluoromethyl)-1,2-dihydropyridine-3-carboxamides. These compounds act as modulators of HSD17B13, an enzyme involved in the metabolism of bile acids and cholesterol. Modulating HSD17B13 activity can have therapeutic benefits in treating liver diseases, metabolic disorders, and other related conditions.
Furthermore, 7-Methylchroman-4-one can be utilized in the development of methods for modulating HSD17B13 activity, which may lead to the discovery of novel therapeutic approaches for various diseases and conditions. 7-Methyl-2,3-dihydro-4H-1-benzopyran-4-one's role in the synthesis of bioactive molecules highlights its importance in the pharmaceutical industry and its potential to contribute to the advancement of medicine.

Upstream product

• 25173-36-8 3-(3-methylphenoxy)propionic acid 
• 5751-51-9 7-methyl-4H-benzopyran-4-one 
• 5751-52-0 7-methoxy-4H-chromen-4-one 
• 94719-81-0 ω-formyl-4'-methoxy-2'-hydroxyacetophenone 
• 13030-21-2 3-(m-methylphenoxy)propan-1-ol 
• 108-39-4 3-methyl-phenol 
• 106-44-5 p-cresol 
• 52449-00-0 3-(4-methylphenoxy)propan-1-ol 
• 25173-37-9 3-(4-methylphenoxy)propionic acid 
• 108-46-3 recorcinol 
• 151884-07-0 2',4'-dihydroxy-3-chloropropiophenone 
• 76240-27-2 7-hydroxy-2,3-dihydro-4H-chromen-4-one 
• 594-27-4 tetramethylstannane 
• 151884-08-1 4-oxochroman-7-yl trifluoromethanesulfonate 

Downstream Products

• 720684-40-2 (4-isocyanato-7-methyl-chroman-4-yl)-phenyl-diazene 
• 828913-34-4 C₁₇H₁₇N₃O₂ 
• 720684-45-7 (4-chloro-phenyl)-(4-isocyanato-7-methyl-chroman-4-yl)-diazene 
• 5751-51-9 7-methyl-4H-benzopyran-4-one 
• 74599-72-7 3-(2-Hydroxy-benzyl)-7-methyl-chroman-4-one 
• 74599-76-1 3-(2-Hydroxy-benzyl)-7-methyl-chroman-4-ol 
• 742679-35-2 7-methylchroman-4-amine 

Relevant articles and documents

MODULATORS OF HSD17B13 AND METHODS OF USE THEREOF

The disclosure relates to compounds and pharmaceutical compositions capable of modulating the hydroxysteroid 17-beta dehydrogenase (HSD17B) family member proteins including inhibiting the HSD17B member proteins, e.g. HSD17B13. The disclosure further relates to methods of treating liver diseases, disorders, or conditions with the compounds and pharmaceutical compositions disclosed herein, in which the HSD17B family member protein plays a role.

Enantioselective halogenative semi-pinacol rearrangement: Extension of substrate scope and mechanistic investigations

The present Full Paper article discloses a survey of our recent results obtained in the context of the enantioselective halogenation-initiated semi-pinacol rearrangement. Commencing with the fluorination/semi-pinacol reaction first and moving to the heavier halogens (bromine and iodine) second, the scope and limitations of the halogenative phase-transfer methodology will be discussed and compared. An extension of the fluorination/semi-pinacol reaction to the ring-expansion of five-membered allylic cyclopentanols will be also described, as well as some preliminary results on substrates prone to desymmetrization will be given. Finally, the present manuscript will culminate with a detailed mechanistic investigation of the canonical fluorination/semi-pinacol reaction. Our mechanistic discussion will be based on in situ reaction progress monitoring, complemented with substituent effect, kinetic isotopic effect and non-linear behaviour studies.

Design and synthesis of HIV-1 protease inhibitors for a long-acting injectable drug application

The design and synthesis of novel HIV-1 protease inhibitors (PIs) (1-22), which display high potency against HIV-1 wild-type and multi-PI-resistant HIV-mutant clinical isolates, is described. Lead optimization was initiated from compound 1, a Phe-Phe hydroxyethylene peptidomimetic PI, and was directed towards the discovery of new PIs suitable for a long-acting (LA) injectable drug application. Introducing a heterocyclic 6-methoxy-3-pyridinyl or a 6-(dimethylamino)-3-pyridinyl moiety (R3) at the para-position of the P1′ benzyl fragment generated compounds with antiviral potency in the low single digit nanomolar range. Halogenation or alkylation of the metabolic hot spots on the various aromatic rings resulted in PIs with high stability against degradation in human liver microsomes and low plasma clearance in rats. Replacing the chromanolamine moiety (R1) in the P2 protease binding site by a cyclopentanolamine or a cyclohexanolamine derivative provided a series of high clearance PIs (16-22) with EC50s on wild-type HIV-1 in the range of 0.8-1.8 nM. PIs 18 and 22, formulated as nanosuspensions, showed gradual but sustained and complete release from the injection site over two months in rats, and were therefore identified as interesting candidates for a LA injectable drug application for treating HIV/AIDS.