17553-86-5

Basic information

• Product Name: (S)-(+)-2,3,7,7A-TETRAHYDRO-7A-METHYL-1H
• Synonyms: (S)-(+)-2,3,7,7A-TETRAHYDRO-7A-METHYL-1H;(S)-(+)-2,3,7,7ALPHA-TETRAHYDRO-7ALPHA-METHYL-1H- INDENE-1,5(6H)-DIONE 90%;(+)-5,6,7,8-Tetrahydro-8-methylindan-1,5-dione, (S)-(+)-Hajos-Parrish diketone, (S)-Hajos dione, (S)-Hajos ketone, (S)-Hajos-Wiechert ketone, (+)-7,7a-Dihydro-7α, β-methyl-1,5(6H)-indandione;(S)-(+)-2,3,7,7a-Ttetrahydro-7a-methyl-1H- indene-1,5(6H)-dione, 90%;(S)-(+)-2,3,7,7a-Tetrahydro-7a-methyl-1H-indene-1,5(6H)-dione,90%;(+)-7,7a-Dihydro-7α, β-methyl-1,5(6H)-indandione;(S)-(+)-5,6,7,8-Tetrahydro-8-Methylindan-1,5-dione;(+)-7,7a-Dihydro-7aβ-Methyl-1,5(6H)-indandione
• CAS NO: 17553-86-5
• Molecular Formula: C₁₀H₁₂O₂
• Molecular Weight: 164.203
• Product Categories: Aromatics;Intermediate
• Mol File: 17553-86-5.mol
• Article Data: 46

Chemical Properties

• Melting Point: 57-64 °C
• Boiling Point: 231.67°C (rough estimate)
• Flash Point: 116.192 °C
• Appearance: White to yellow to beige/Crystalline Powder, Crystals and/or Chunks
• Density: 1.0041 (rough estimate)
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.5480 (estimate)
• Storage Temp.: Refrigerator
• Solubility: Chloroform, Methanol
• BRN: 1619112
• CAS DataBase Reference: (S)-(+)-2,3,7,7A-TETRAHYDRO-7A-METHYL-1H(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(+)-2,3,7,7A-TETRAHYDRO-7A-METHYL-1H(17553-86-5)
• EPA Substance Registry System: (S)-(+)-2,3,7,7A-TETRAHYDRO-7A-METHYL-1H(17553-86-5)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38-43
• Safety Statements: 26-36/37-39
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 1
• Hazardous Substances Data: 17553-86-5(Hazardous Substances Data)

Usage

Chemical Properties

White to beige crystalline powder

Uses

Different sources of media describe the Uses of 17553-86-5 differently. You can refer to the following data:
1. An intermediate in the Indenedione preparation.
2. (S)-(+)-Hajos-Parrish diketone can be used as a reactant in: The total synthesis of steroidal alkaloids cortistatins. The stereoselective preparation of hydroanthracenol and related polycyclic compounds via Ti(Oi-Pr)4-promoted photoenolization Diels-Alder reaction. The synthesis of γ,γ-disubstituted allyldiboron compounds by reacting with allylic 1,1-diboronate reagents via Cu-catalyzed borylation and 1,2-addition reaction.

InChI:InChI=1/C10H12O2/c1-10-5-4-8(11)6-7(10)2-3-9(10)12/h6H,2-5H2,1H3/t10-/m0/s1

Upstream product

• 35544-95-7 (3aR,7aR)-3a-hydroxy-7a-methylperhydroindene-1,5-dione 
• 33879-04-8 (+)-(3aS,7aS)-2,3,3a,4,7,7a-hexahydro-3a-hydroxy-7a-methyl-1H-indene-1,5(6H)-dione 
• 25112-78-1 2-methyl-2-(3-oxobutyl)-1,3-cyclopentanedione 
• 5870-63-3 3-hydroxy-2-methyl-2-cyclopenten-1-one 
• 99780-84-4 (7aR)-1t-hydroxy-7a-methyl-(7ar)-1,2,3,6,7,7a-hexahydro-inden-5-one 
• 765-69-5 2-Methylcyclopentane-1,3-dione 
• 78-94-4 methyl vinyl ketone 
• 16271-49-1 (1S,7aS)-1-hydroxy-7a-methyl-2,3,7,7a-tetrahydro-1H-inden-5(6H)-one 
• 16271-45-7 rac.-7,7a-Dihydro-1β-hydroxy-7aβ-methyl-5(6H)-indanon-hydrogenphthalat 
• 16271-49-1 1β-hydroxy-7aβ-methyl-2,3,7,7a-tetrahydro-1H-inden-5(6H)-one 
• 1120-72-5 2-Methylcyclopentanone 
• 4326-84-5 2-Methyl-2-(3-oxobutyl)cyclopentanone 
• 5817-26-5 ethyl (2S)-pyrrolidine-2-carboxylate 
• 308278-25-3 methyl (S)-9-diethoxyphosphoryl-5-methoxycarbonyl-5-methyl-4,8-dioxononanoate 

Downstream Products

• 1944-63-4 3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione 
• 5173-46-6 4,9-Androstadiene-3,17-dione 
• 6218-29-7 17β-hydroxyestra-4,9-dien-3-one 
• 126971-22-0 (1R,3aS,7aS)-7a-Methyl-1-phenyl-1,4,5,6,7,7a-hexahydro-1,3a-etheno-indene-9-carbaldehyde 
• 149790-00-1 Toluene-4-sulfonic acid (1R,3aS,4S,5R,7aR)-1-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-7a-methyl-4-(2-trimethylsilanyl-ethoxymethoxy)-octahydro-inden-4-ylmethyl ester 
• 149789-96-8 (1R,3aS,4S,5R,7aR)-5-Benzyloxy-4-benzyloxymethyl-1-(tert-butyl-dimethyl-silanyloxy)-7a-methyl-4-(2-trimethylsilanyl-ethoxymethoxy)-octahydro-indene 
• 64675-08-7 dinordrin 
• 161489-22-1 C₂₁H₂₂O₄ 
• 126971-20-8 (9S)-1-Hydroxy-9-methyl-1-phenylbicyclo<4.3.0>nona-4(5)-ene 
• 126971-23-1 C₂₀H₂₀O₃ 
• 126971-21-9 (9S)-9-Methyl-1-phenylbicyclo<4.3.0>nona-1(2),3(4)-diene 

Relevant articles and documents

β-Homoamino acids as catalysts in enantioselective intra- and intermolecular aldol reactions

β3-Homoamino acids catalyze the intra- (cf. the Hajos-Parrish-Eder-Sauer-Wiechert reaction) as well as the intermolecular aldol reaction. The stereochemical outcome with selectivities of up to 83% ee is reversed in the intramolecular reaction,

Protecting-group-free total synthesis of aplykurodinone-1

A concise, stereoselective, and protecting-group-free total synthesis of aplykurodinone-1 from Hajos-Parrish ketone was described. The synthetic approach features a sequence of aerobic allylic oxidation and elimination of alcohol 9. The key intermediate for this synthesis was formed by a stereoselective intramolecular radical cyclization.

Inotropic activity of hydroindene amidinohydrazones

Several hydroindenic derivatives (7a-methyl-2,3,5,6,7,7a-hexahydro-1H-indenes), bearing an amidinohydrazone at C-5 and different moieties at C-1, have been synthesized and evaluated for their inotropic and chronotropic effects on right- and left-guinea-pig-atria activity. Three of them showed the same profile as digoxin, although with lower potency. The effect on Na+,K+ ATPase (NKA) was also evaluated for these three compounds, observing that two of them, with the same absolute configuration as natural cardenolides, are also NKA inhibitors, while the compound with the opposite configuration lacks such an effect. More interestingly, both active compounds act without affecting the cardiac rhythm. This could be related to the selective inhibition of the human α2β1 isozyme (associated with the inotropic effect) with respect to the α1β1 isozyme (associated with the maintenance of basal ionic levels in the cell and the toxic effect of cardenolides).

Construction of key building blocks towards the synthesis of cortistatins

This work reports the construction of key building blocks towards the synthesis of cortistatins; a family of steroidal alkaloids. Cortistatin A, being a primary target due to its superior biological properties over other congeners, has been prepared by two different synthetic routes. Synthesis of the precursor to the heavily substituted A-ring starting from d-glucose and construction of the DE-ring junction employing a Hajos-Parrish ketone as a chiral pool have been demonstrated. Efforts are underway to assemble these key fragments and build towards the total synthesis of cortistatin A.

A Highly Active Polymer-Supported Catalyst for Asymmetric Robinson Annulations in Continuous Flow

The preparation through Robinson annulation of enantiopure building blocks with both academic and industrial relevance, such as the Wieland-Miescher and Hajos-Parrish ketones, has suffered from important drawbacks, such as the need for high catalyst loading or extremely long reaction times. Here we report a heterogenized organocatalyst based on Luo's diamine for fast and broad-scope enantioselective Robinson annulation reactions. The polystyrene-supported diamine 19a enables the high-yield, highly enantioselective preparation of a wide range of chiral bicyclic enones under mild conditions, with reaction times as short as 60 min (batch) or residence times of 10 min (flow). In contrast with its homogeneous counterpart 19b, the catalytic resin 19a experiences a notable increase in catalytic activity with temperature in 2-MeTHF (a 10-fold decrease in reaction times without erosion in enantioselectivity is observed from room temperature to 55 °C). The scope of the transformation in batch mode has been illustrated with 14 examples, including examples only reported in poorly enantioenriched (22n) or in racemic form (22k). Enantiopure 22k has been used as the starting material for a straightforward formal synthesis of the antibiotic and antifeedant sesquiterpene (-)-isovelleral (24). The heterogenized catalyst 19a admits extended recycling (10 cycles) and has been used to develop the first asymmetric Robinson annulations in continuous flow. The potential of the flow process is illustrated by the large-scale preparation of the Wieland-Miescher ketone (65 mmol in 24 h of operation, TON of 117) and by a sequential flow experiment leading to a library of eight enantioenriched diketone compounds.

Pyrimidine-derived prolinamides as recoverable bifunctional organocatalysts for enantioselective inter- and intramolecular aldol reactions under solvent-free conditions

Chiral L-prolinamides 2 containing the (R,R)- and (S,S)-trans-cyclohexane-1,2-diamine scaffold and a 2-pyrimidinyl unit are synthesized and used as general organocatalysts for intermolecular and intramolecular aldol reactions with 1,6-hexanedioic acid as a co-catalyst under solvent-free conditions. The intermolecular reaction between ketone-aldehyde and aldehyde-aldehyde must be performed under wet conditions with catalyst (S,S)-2b at 10 °C, which affords anti-aldols with high regio-, diastereo-, and enantioselectivities. For the Hajos-Parrish-Eder-Sauer-Wiechert reaction, both diastereomers of catalyst 2 give similar results at room temperature in the absence of water to give the corresponding Wieland-Miescher ketone and derivatives. Both types of reactions were scaled up to 1 g, and the organocatalysts were recovered by extractive workup and reused without any appreciable loss in activity. DFT calculations support the stereochemical results of the intermolecular process and the bifunctional role played by the organocatalyst by providing a computational comparison of the H-bonding networks occurring with catalysts 2a and 2b. The intermolecular ketone-aldehyde and aldehyde-aldehyde aldol reactions and the Hajos-Parrish-Eder-Sauer-Wiechert versions with the employment of chiral L-prolinamides containing the (R,R)- and (S,S)-trans-cyclohexane-1,2-diamine scaffold and a 2-pyrimidinyl unit are successfully performed under solvent-free conditions; WMK = Wieland-Miescher ketone.