4242-00-6

Basic information

• Product Name: (4aS,5S)-5-hydroxy-4a-methyl-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one
• Synonyms: 5-hydroxy-4a-methyl-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one
• CAS NO: 4242-00-6
• Molecular Formula: C₁₁H₁₆O₂
• Molecular Weight: 180.2435
• Mol File: 4242-00-6.mol
• Article Data: 30

Chemical Properties

• Boiling Point: 328.2°C at 760 mmHg
• Flash Point: 139.4°C
• Density: 1.11g/cm³
• Vapor Pressure: 1.44E-05mmHg at 25°C
• Refractive Index: 1.533
• CAS DataBase Reference: (4aS,5S)-5-hydroxy-4a-methyl-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: (4aS,5S)-5-hydroxy-4a-methyl-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one(4242-00-6)
• EPA Substance Registry System: (4aS,5S)-5-hydroxy-4a-methyl-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one(4242-00-6)

Safety Data

• Hazardous Substances Data: 4242-00-6(Hazardous Substances Data)

Usage

Description

(4aS,5S)-5-hydroxy-4a-methyl-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one is a synthetic organic compound characterized by its cyclic ketone structure and a hexahydronaphthalene core. It features a molecular formula of C11H16O2 and is distinguished by the presence of a hydroxy and methyl group attached to it. (4aS,5S)-5-hydroxy-4a-methyl-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one is known for its potential applications in various fields due to its unique structural features and functional groups.

Uses

Used in Organic Synthesis and Medicinal Chemistry:
(4aS,5S)-5-hydroxy-4a-methyl-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one is utilized as a building block in the creation of various pharmaceuticals and fine chemicals. Its unique structure and functional groups make it a valuable component in the development of new drugs and other chemical products.
Used in Drug Discovery and Development:
Due to its structural features and functional groups, (4aS,5S)-5-hydroxy-4a-methyl-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one holds promise in the field of drug discovery and development. It can be used to design and synthesize novel compounds with potential therapeutic applications.
Used in Perfumery and Personal Care Products:
(4aS,5S)-5-hydroxy-4a-methyl-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one may also find application as a fragrance ingredient in the perfumery and personal care products industry. Its unique scent profile can contribute to the creation of distinct and appealing fragrances for various consumer products.

Upstream product

• 20007-99-2 Wieland-Miescher ketone 
• 33878-99-8 (S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione 
• 118832-69-2 [(4S,5S)-5-(Hydroxy-diphenyl-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-diphenyl-methanol; compound with (S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione 
• 50302-16-4 (4aS,5S)-5-Hydroxy-4a-methyl-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one 
• 141-75-3 butyryl chloride 
• 32042-78-7 acetic acid (1S*,8aS*)-(+/-)-8a-methyl-6-oxo-1,2,3,4,6,7,8,8a-octahydronaphthalen-1-yl ester 
• 4087-39-2 (S)-(+)-4,4a,5,6,7,8-hexahydro-4a-methyl-2(3H)-naphthalenone 
• 108-05-4 vinyl acetate 
• 13304-34-2 8a-Methyl-1,2,3,4,6,7,8,8a-octahydro-naphthalen-1-ol 
• 100052-83-3 8a-Methyl-1,2,3,4,6,7,8,8a-octahydro-naphthalene-1,6-diol 

Downstream Products

• 878-47-7 (4aS,5S)-4,4a,5,6,7,8-hexahydro-5-hydroxy-4a-methylnaphthalen-2(3H)-one 
• 53662-94-5 (4aS,5S)-5-tert-Butoxy-4a-methyl-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one 
• 32042-79-8 (+)-(4aS,5S)-5-benzoyloxy-4,4a,5,6,7,8-hexahydro-4a-methylnaphthalen-2(3H)-one 
• 61950-53-6 1β-tert-butoxy-8aβ-methyl-1,2,3,4,6,7,8,8a-octahydronaphthalen-6-one 
• 4242-06-2 5-Benzylthio-8-methyl-1,2,3,4-tetrahydro-naphthalin 
• 4242-04-0 5-Benzyloxy-8-methyl-1,2,3,4-tetrahydro-naphthalin 
• 53662-94-5 (4aS,5R)-5-(t-Butoxy)-4a-methyl-4,4a,5,6,7,8-hexahydro-3H-naphthalin-2-on 
• 20007-99-2 Wieland-Miescher ketone 
• 33878-99-8 (S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione 
• 943348-11-6 tert-butyldimethyl-((1S,6S,8aS)-8a-methyl-6-(2-(phenylsulfinyl)ethoxy)-1,2,3,4,6,7,8,8a-octahydronaphthalen-1-yloxy)silane 
• 327968-79-6 (4aS,5S)-4a-Methyl-1-phenylsulfanylmethyl-5-(tetrahydro-pyran-2-yloxy)-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one 
• 155588-13-9 (2aR,4S,4aS,6R,11S,12S,12aR,12bS)-12-benzoyloxy-11-hydroxy-4a,8,13,13-tetramethyl-5-oxo-4-triethylsilyloxy-3,4,4a,5,6,9,10,11,12,12a-decahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxete-6,12b(2aH)diyl diacetate 
• 168421-83-8 (2aR,4S,4aS,8aS,8bS)-8b-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-4a-methyl-octahydro-2-oxa-cyclobuta[a]naphthalen-7-one 
• 168421-62-3 [(1S,2S,3S,4S,6R)-1-Benzyloxy-3-(2,2-dimethoxy-ethyl)-3-methyl-2-vinyl-7-oxa-bicyclo[4.2.0]oct-4-yloxy]-tert-butyl-dimethyl-silane 

Relevant articles and documents

Total syntheses of the sesquiterpenes β-corymbolol and corymbolone

The first total synthesis of racemic corymbolone, an eudesmane sesquiterpene isolated from Cyperus species used in traditional medicine to treat many diseases, is reported. In the developed sequence, the immediate precursor of corymbolone is the diol β-corymbolol, an epimer at C1 of the natural α-corymbolol. Thus, starting from the readily available Wieland-Miescher Ketone, the title compounds were achieved in 11 and 12 steps, respectively, in ca. 3% overall yield.

Biocatalytic Approaches to the Enantiomers of Wieland–Miescher Ketone and its Derivatives

Biocatalytic approaches have been investigated in order to isolate the enantiomers of Wieland–Miescher ketone (1) and of its alcoholic derivatives (cis-2 and trans-3). Specifically, two enzymes from our in-house metagenomic collection of oxidoreductases, IS2-SDR and Dm7α-HSDH, catalyzed the kinetic resolution of the starting racemic ketone 1 or its complete conversion into two diastereomeric products, respectively. Moreover, the kinetic resolution of the racemic cis-alcohol (2) was very efficiently obtained (E?2.000) by lipase PS catalyzed acetylation in dry acetone. All the products were isolated with ee≥95 %. Simple chemical elaborations of some of them allowed to isolate the missing enantiomers.

Total synthesis of JBIR-03 and asporyzin C

The first enantioselective total synthesis of JBIR-03 and asporyzin C, indole diterpenoids of fungal origin exhibiting a range of pharmacologically important biological activities, has been accomplished from a known bicyclic keto alcohol in 13 and 14 steps, respectively. A hydroxy-directed cyclopropanation and Pd(II)-mediated indole ring formation were exploited as the key steps to obtain a pivotal pentacylic intermediate, which was converted into asporyzin C via chain elongation using cross-metathesis and then into JBIR-03 by Pd(II)-catalyzed tetrahydrofuran ring formation in an exclusively diastereoselective manner.

CONTRACEPTIVE AGENTS

The invention provides compounds of formula I, II, III, or IV: wherein R1 to R11, X, and Y have any of the values defined in the specification. The compounds inhibit Na, K-ATPase α4 and are useful as contraceptive agents.