9,9-Dimethyl-3-methylidene-2-oxooctahydro-3a,7-ethanoindene-4-carboxylic acid

Base Information

• Chemical Name: 9,9-Dimethyl-3-methylidene-2-oxooctahydro-3a,7-ethanoindene-4-carboxylic acid
• CAS No.: 83058-94-0
• Molecular Formula: C₁₅H₂₀O₃
• Molecular Weight: 248.322
• DSSTox Substance ID: DTXSID501003101
• Wikidata: Q105178391
• Mol file: 83058-94-0.mol

Synonyms:DTXSID501003101;9,9-Dimethyl-3-methylidene-2-oxooctahydro-3a,7-ethanoindene-4-carboxylic acid

Chemical Property of 9,9-Dimethyl-3-methylidene-2-oxooctahydro-3a,7-ethanoindene-4-carboxylic acid

Chemical Property:

• Vapor Pressure: 5.43E-08mmHg at 25°C
• Boiling Point: 413.4°C at 760 mmHg
• Flash Point: 218°C
• PSA: 85.18000
• Density: 1.18g/cm³
• LogP: 1.58340
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 248.14124450
• Heavy Atom Count: 18
• Complexity: 462

Purity/Quality:

99% ^*data from raw suppliers

TerrecyclicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CC2CCC(C13C2CC(=O)C3=C)C(=O)O)C
• Isomeric SMILES: CC1(C[C@H]2CC[C@H]([C@@]13[C@@H]2CC(=O)C3=C)C(=O)O)C
• Uses: Terrecyclic acid is a sesquiterpene metabolite produced by Aspergillus terreus, first reported by researchers at the Universities of Osaka and Tokyo in 1982. Terrecyclic acid possesses broad spectrum antimicrobial and antitumor activity. Terrecyclic acid induces the heat shock protein response and affects oxidative and inflammatory cellular stress response pathways. No studies of the mode of action of terrecyclic acid have been published. Terrecyclic Acid is an antimicrobial which induces heat shock protein response.

Technology Process of 9,9-Dimethyl-3-methylidene-2-oxooctahydro-3a,7-ethanoindene-4-carboxylic acid

There total 19 articles about 9,9-Dimethyl-3-methylidene-2-oxooctahydro-3a,7-ethanoindene-4-carboxylic acid 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: 94.0%

(3R*,3aR*,7R*,7S*)-octahydro-3-(hydroxymethyl)-8,8-dimethyl-2-oxo-3a,7-ethano-3aH-indene-4-carboxylic acid (78739-66-9,117557-25-2,132831-49-3,132831-50-6) → (3aR*,4S*,7S*,7aS*)-octahydro-8,8-dimethyl-3-methylene-2-oxo-3a,7-ethano-3aH-indene-4-carboxylic acid (78739-67-0,83058-94-0,93219-11-5)

Guidance literature:

With toluene-4-sulfonic acid; In benzene; at 40 - 50 ℃; for 0.333333h;

DOI:10.1021/ja00404a026

Reference yield: 67.0%

(2R,3S,3aS,4S,7S,7aS)-3-Acetoxymethyl-2-hydroxy-8,8-dimethyl-octahydro-3a,7-ethano-indene-4-carboxylic acid (79060-04-1) → (3aR*,4S*,7S*,7aS*)-octahydro-8,8-dimethyl-3-methylene-2-oxo-3a,7-ethano-3aH-indene-4-carboxylic acid (78739-67-0,83058-94-0,93219-11-5)

Guidance literature:

With pyridinium chlorochromate;

DOI:10.1021/ja00405a091

Reference yield:

(1R*,6S*,7S*)-10,10-dimethyl-4-oxotricyclo<4.3.2.02,6>undec-2-en-7-carboxylic acid (78739-64-7,82978-37-8,102849-98-9,117557-24-1,132831-32-4) → (3aR*,4S*,7S*,7aS*)-octahydro-8,8-dimethyl-3-methylene-2-oxo-3a,7-ethano-3aH-indene-4-carboxylic acid (78739-67-0,83058-94-0,93219-11-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) lithium diisopropylamide / 1.) THF, -23 deg C, 1.25 h, 2.) 5 min

2: hydrogen / 5percent Pd-C / methanol / 1 h / Ambient temperature

3: 190 - 195 °C

With hydrogen; lithium diisopropyl amide; palladium on activated charcoal; In methanol;

DOI:10.1021/ja00404a026

upstream raw materials:

sodium acetate

(2R,3S,3aS,4S,7S,7aS)-3-Acetoxymethyl-2-hydroxy-8,8-dimethyl-octahydro-3a,7-ethano-indene-4-carboxylic acid

(3aS,4S,7S,7aS)-3-Hydroxymethyl-8,8-dimethyl-2-oxo-octahydro-3a,7-ethano-indene-4-carboxylic acid

(3R*,3aR*,7R*,7S*)-octahydro-3-(hydroxymethyl)-8,8-dimethyl-2-oxo-3a,7-ethano-3aH-indene-4-carboxylic acid

Downstream raw materials:

(+/-)-quadrone

isoquadrone

Refernces

• 1、 Cane, David E.,Whittle, Yvonne G.,Liang, Tzyy-Chyau. "THE BIOSYNTHESIS OF QUADRONE AND TERRECYCLIC ACID". . p. 1119 - 1122. Retrieved 2007/10/02.
• 2、 Danishefsky, Samuel,Vaughan, Kenward,Gadwood, Robert,Tsuzuki, Kazuo. "The Total Synthesis of dl-Quadrone". . p. 4136 - 4141. Retrieved 2007/10/02.