(S)-4,7a-Dimethyl-2,3,7,7a-tetrahydro-6H-indene-1,5-dione

Base Information

• Chemical Name: (S)-4,7a-Dimethyl-2,3,7,7a-tetrahydro-6H-indene-1,5-dione
• CAS No.: 33878-96-5
• Molecular Formula: C₁₁H₁₄O₂
• Molecular Weight: 178.231
• Hs Code.: 2914790090
• DSSTox Substance ID: DTXSID401345748
• Nikkaji Number: J184.245E
• Wikidata: Q63409859
• Mol file: 33878-96-5.mol

Synonyms:(S)-4,7a-Dimethyl-2,3,7,7a-tetrahydro-6H-indene-1,5-dione;33878-96-5;SCHEMBL11456003;DTXSID401345748;(7AS)-4,7A-DIMETHYL-2,3,6,7-TETRAHYDROINDENE-1,5-DIONE;AKOS006281664;AB45989;Q63409859;(S)-2,3,7,7A-TETRAHYDRO-4,7A-DIMETHYL-1H-INDENE-1,5(6H)-DIONE

Chemical Property of (S)-4,7a-Dimethyl-2,3,7,7a-tetrahydro-6H-indene-1,5-dione

Chemical Property:

• Vapor Pressure: 0.000606mmHg at 25°C
• Melting Point: 126-128 °C
• Boiling Point: 310.3±31.0 °C(Predicted)
• Density: 1.11±0.1 g/cm3(Predicted)
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 178.099379685
• Heavy Atom Count: 13
• Complexity: 325

Purity/Quality:

98%min ^*data from raw suppliers

(S)-4,7a-Dimethyl-2,3,7,7a-tetrahydro-6H-indene-1,5-dione ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=C2CCC(=O)C2(CCC1=O)C
• Isomeric SMILES: CC1=C2CCC(=O)[C@]2(CCC1=O)C

Technology Process of (S)-4,7a-Dimethyl-2,3,7,7a-tetrahydro-6H-indene-1,5-dione

There total 8 articles about (S)-4,7a-Dimethyl-2,3,7,7a-tetrahydro-6H-indene-1,5-dione which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 78.0%

2-(3-oxopentyl)-2-methylcyclopentane-1,3-diones (34927-37-2) → (7aS)-(+)-4,7a-dimethyl-2,3,7,7a-tetrahydro-1H-indene-1,5(6H)-dione (33878-96-5) + (-)-(7aR)-4,7a-dimethyl-2,3,7,7a-tetrahydro-6H-indene-1,5-dione

Guidance literature:

With hexamethylimidazolium hexafluorophosphate; D-(R)-phenylalanine; (1S)-10-camphorsulfonic acid; In various solvent(s); at 20 - 70 ℃; Title compound not separated from byproducts;

DOI:10.1055/s-2007-970740

Reference yield: 60.0%

2-(3-oxopentyl)-2-methylcyclopentane-1,3-diones (34927-37-2) → (7aS)-(+)-4,7a-dimethyl-2,3,7,7a-tetrahydro-1H-indene-1,5(6H)-dione (33878-96-5)

Guidance literature:

With L-phenylalanine; (1S)-10-camphorsulfonic acid; In acetonitrile; at 25 - 70 ℃; for 120h;

DOI:10.1002/chem.200500513

Reference yield:

2-Methylcyclopentane-1,3-dione (765-69-5) + 4-penten-3-one (1629-58-9) → (7aS)-(+)-4,7a-dimethyl-2,3,7,7a-tetrahydro-1H-indene-1,5(6H)-dione (33878-96-5) + (-)-(7aR)-4,7a-dimethyl-2,3,7,7a-tetrahydro-6H-indene-1,5-dione

Guidance literature:

With perchloric acid; L-valine; toluene-4-sulfonic acid; acetic acid; Multistep reaction. Title compound not separated from byproducts;

DOI:10.1021/ja00104a012

upstream raw materials:

2-Methylcyclopentane-1,3-dione

4-penten-3-one

2-(3-oxopentyl)-2-methylcyclopentane-1,3-diones

Refernces

• 1、 Paquette, Leo A.,Wang, Ting-Zhong,Sivik, Matthew R.. "Total synthesis of (-)-austalide B. A generic solution to elaboration of the Pyran/p-Cresol/Butenolide triad". . p. 11323 - 11334. Retrieved 1994.
• 2、 Clot-Almenara, Lidia,Rodríguez-Escrich, Carles,Pericàs, Miquel A.. "Desymmetrisation of: Meso -diones promoted by a highly recyclable polymer-supported chiral phosphoric acid catalyst". . p. 6910 - 6914. Retrieved 2018/02/23.
• 3、 Tao, Daniel J.,Slutskyy, Yuriy,Overman, Larry E.. "Total Synthesis of (-)-Chromodorolide B". supporting information. p. 2186 - 2189. Retrieved 2016/03/08.