66251-18-1

Basic information

• Product Name: (1R,3aR,7aR)-7a-Methyl-1-((R)-6-Methylheptan-2-yl)hexahydro-1H-inden-4(2H)-one
• Synonyms: (1R,3aR,7aR)-7a-Methyl-1-((R)-6-Methylheptan-2-yl)hexahydro-1H-inden-4(2H)-one;4H-Inden-4-one,1-[(1R)-1,5-dimethylhexyl]- octahydro-7a-methyl-,(1R,3aR,7aR)-;Grundmann's Ketone
• CAS NO: 66251-18-1
• Molecular Formula: C₁₈H₃₂O
• Molecular Weight: 264.44608
• Mol File: 66251-18-1.mol
• Article Data: 23

Chemical Properties

• Boiling Point: bp0.001 115-120°
• Appearance: /
• Density: 0.921±0.06 g/cm3(Predicted)
• Solubility: DCM, Ethyl Acetate
• CAS DataBase Reference: (1R,3aR,7aR)-7a-Methyl-1-((R)-6-Methylheptan-2-yl)hexahydro-1H-inden-4(2H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,3aR,7aR)-7a-Methyl-1-((R)-6-Methylheptan-2-yl)hexahydro-1H-inden-4(2H)-one(66251-18-1)
• EPA Substance Registry System: (1R,3aR,7aR)-7a-Methyl-1-((R)-6-Methylheptan-2-yl)hexahydro-1H-inden-4(2H)-one(66251-18-1)

Safety Data

• Hazardous Substances Data: 66251-18-1(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 66251-18-1 differently. You can refer to the following data:
1. Intermediate in the synthesis of vitamin D active compounds.
2. Grundmann''s Ketone is an intermediate in synthesizing (7Z)-Calcipotriene (C144225), which is an isomeric impurity of Calcipotriene (1442000), a vitamin D3 analogue with low calcemic activity.

Upstream product

• 33813-99-9 Grundmann's alcohol 
• 156896-63-8 (1R,3aR,4R,7aR)-1-[(R)-1,5-dimethylhexyl]-7a-methyloctahydro-1H-inden-4-ol 
• 1527523-12-1 (1R,3aR,7aR)-7a-methyl-1-((R)-6-methylheptan-2-yl)octahydro-1H-inden-4-ol 
• 434-16-2 7-dehydrocholesterol 
• 96843-42-4 (-)-<1(S)-methyl-2(S)-((phenylsulfonyl)methyl)-5(R)-(1(S)-((tosyloxy)methyl)-5-methylhexyl)cyclopentyl>acetaldehyde ethylene acetal 
• 96700-57-1 Methanesulfonic acid (3R,3aR,7R,7aR)-7-benzenesulfonyl-3-((R)-1,5-dimethyl-hexyl)-3a-methyl-octahydro-inden-5-yl ester 
• 96843-40-2 (+)-6-methyl-2(R)-<2-((2,5-dioxacyclopentyl)methyl)-2(S)-methyl-3(S)-((phenylsulfonyl)methyl)-1(R)-cyclopentyl>heptanoic acid 
• 96862-14-5 (-)-2(S)-methyl-2-<3-(mesyloxy)propyl>-1(S)-<(phenylsulfonyl)methyl>-3(R)-(1(R),5-dimethylhexyl)cyclopentane 
• 96843-41-3 (+)-<1(S)-methyl-2(S)-((phenylsulfonyl)methyl)-5(R)-(1(S)-(hydroxymethyl)-5-methylhexyl)cyclopentyl>acetaldehyde ethylene acetal 
• 105764-33-8 (R)-2-[(1R,2R,3R)-3-Benzenesulfonylmethyl-2-methyl-2-(2-oxo-ethyl)-cyclopentyl]-6-methyl-heptanoic acid 
• 96843-39-9 (-)-(1S,3aR,4R,7aS)-5-acetoxy-1-<(phenylsulfonyl)methyl>-4-(4-methylpentyl)-3a,4,7,7a-tetrahydro-7a-methylindan 
• 96843-43-5 (-)-<1(S)-methyl-2(S)-((phenylsulfonyl)methyl)-5(R)-(1(R),5-dimethylhexyl)cyclopentyl>acetaldehyde ethylene acetal 
• 96843-37-7 C₂₅H₃₆O₄S 
• 96843-38-8 (-)-(1S,3aR,4R,7aS)-1-<(phenylsulfonyl)methyl>-4-(4-methylpentyl)-3a,4,5,6,7,7a-hexahydro-7a-methylindan-5-one 

Downstream Products

• 869101-47-3 (1R,3aR,5R,7aR)-1-((R)-1,5-Dimethyl-hexyl)-7a-methyl-5-[2-(2-methylene-cyclohexyl)-ethyl]-octahydro-inden-4-one 
• 343974-25-4 (1R,3aR,5S,7aR)-5-{2-[(S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-ethyl}-1-((R)-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-4-one 
• 108887-35-0 1α,3β-bis(tert-butyldimethylsilyloxy)-9,10-secocholesta-5,7,10(19)-triene 
• 1527523-54-1 (1R,3aS,4R,5S,7aR)-4-(5-methoxy-2-methylphenethyl)-7a-methyl-1-((R)-6-methylheptan-2-yl)-octahydro-1H-inden-5-ol 
• 328570-91-8 (1R,3aS,4S,5R,7aR)-4-(5-methoxy-2-methylphenethyl)-7a-methyl-1-((R)-6-methylheptan-2-yl)-octahydro-1H-inden-5-ol 
• 104121-92-8 Eldecalcitol 
• 144848-24-8 25-[(triethylsilyl)oxy]de-A,B-cholestan-8-one 
• 1357309-33-1 2-{4-[(1R,3aR,7aR)-1-((R)-1,5-dimethylhexyl)-7a-methyl-2,3,3a,6,7,7a-hexahydro-1H-inden-4-yl]but-3-ynyldisulfanyl}phenylamine 
• 84928-42-7 (3aS)-1c-((R)-1,5-dimethyl-hexyl)-7a-methyl-(3ar,7ac)-octahydro-inden-4-one-(2,4-dinitro-phenylhydrazone) 
• 119569-20-9 (3aR)-1t-((R)-1,5-dimethyl-hexyl)-4t-(3,5-dinitro-benzoyloxy)-7a-methyl-(3ar,7at)-hexahydro-indan 
• 134328-85-1 6,7-Dehydro-1α-hydroxyprevitamin D₃ 
• 133447-48-0 (3S,9S,10S)-(Z,Z)-9,10-secocholesta-5,7,14-triene-3,9-diol 
• 133447-48-0 (3S,9S,10R)-(Z,Z)-9,10-secocholesta-5,7,14-triene-3,9-diol 
• 133447-42-4 9α-(benzoyloxy)-(7E)-vitamin D3 tert-butyldimethylsilyl ether 

Relevant articles and documents

Aminopropylindenes derived from Grundmann's ketone as a novel chemotype of oxidosqualene cyclase inhibitors

A series of aminopropylindenes, designed as mimics of a cationic high energy intermediate in the oxidosqualene cyclase1 (OSC)-mediated cyclization of 2,3-oxidosqualen to lanosterol was prepared from Grundmann's ketone. Screening on OSCs from five different organisms revealed interesting activities and selectivities of some of the compounds. A N,N-dimethylaminopropyl derivative showed promising inhibition of Trypanosoma cruzi OSC in combination with low cytotoxicity, and showed significant reduction of cholesterol biosynthesis in a human cell line.

Large-Scale Synthesis of Eldecalcitol

Industrial-scale synthesis of eldecalcitol is described. AA highly diastereoselective epoxidation of p-methoxybenzyl (PMB) protected dienol at room temperature provides the key epoxide intermediate with a secondary hydroxyl group, which is alkylated with a triflate to set up all of the subunits at the C-1, C-2, and C-3 positions of the A-ring fragment. Selective protecting group manipulation followed by palladium-catalyzed cyclization then provides the A-ring synthon. The C/D-ring fragment is obtained by (1) direct C-H hydroxylation of Grundman's ketone using in situ prepared trifluoropropanone dioxirane and (2) protection. Finally, the coupling of the A-ring with the C/D-ring fragment, global deprotection, and recrystallization provide the highly crystalline eldecalcitol.

Structure–Activity Relationship Studies of Vitamin D3 Analogues Containing an Ether or Thioether Linker as Hedgehog Pathway Inhibitors

The Hedgehog (Hh) signaling pathway is critical for embryonic patterning and postembryonic tissue regeneration. Constitutive pathway activation has also been linked to human malignancies such as basal cell carcinoma (BCC) and medulloblastoma; therefore, multiple small-molecule scaffolds that inhibit Hh signaling are in development. Previously, Grundmann's alcohol, also known as the “northern region” of vitamin D3 (VD3), has been identified as a moderate Hh pathway inhibitor. In this study, isomers of Grundmann's alcohol with different orientations of the C4 hydroxy group and C3α proton were investigated to determine the optimal configuration for this hexahydroindane scaffold with respect to Hh inhibition. A series of analogues containing Grundmann's alcohol linked to a substituted phenyl or benzyl ring through an ether or thioether linker were synthesized and evaluated for their anti-Hh activity. Of these, analogue 17 ((1R,3aR,4R,7aR)-1-[(R)-1,5-dimethylhexyl]-4-(4-aminophenoxy)-7a-methyloctahydro-1H-indene) demonstrated potent anti-Hh activity in Hh-dependent BCC cells and did not activate canonical vitamin D receptor signaling, demonstrating its selective nature for the Hh signaling pathway.