62251-98-3

Basic information

• Product Name: coronafacic acid
• Synonyms: coronafacic acid;(3aS)-1-Oxo-6α-ethyl-2,3,3aβ,6,7,7aβ-hexahydro-1H-indene-4-carboxylic acid;(3aS)-2,3,3aβ,6,7,7aβ-Hexahydro-1-oxo-6α-ethyl-1H-indene-4-carboxylic acid;(3aS)-6α-Ethyl-2,3,3aβ,6,7,7aβ-hexahydro-1-oxo-1H-indene-4-carboxylic acid
• CAS NO: 62251-98-3
• Molecular Formula: C₁₂H₁₆O₃
• Molecular Weight: 208.25364
• Mol File: 62251-98-3.mol
• Article Data: 24

Chemical Properties

• Boiling Point: 375.4°C at 760 mmHg
• Flash Point: 195°C
• Appearance: /
• Density: 1.168g/cm³
• Vapor Pressure: 1.14E-06mmHg at 25°C
• Refractive Index: 1.525
• CAS DataBase Reference: coronafacic acid(CAS DataBase Reference)
• NIST Chemistry Reference: coronafacic acid(62251-98-3)
• EPA Substance Registry System: coronafacic acid(62251-98-3)

Safety Data

• Hazardous Substances Data: 62251-98-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C12H16O3/c1-2-7-5-9-8(3-4-11(9)13)10(6-7)12(14)15/h6-9H,2-5H2,1H3,(H,14,15)/t7-,8+,9+/m1/s1

Upstream product

• 62251-96-1 (+)-coronatine 
• 92773-18-7 2-carbethoxy-4-ethylbicyclo<4.3.0>non-3-ene-7,9-dione 
• 92773-19-8 5-carbethoxy-9-chloro-3-ethylbicyclo<4.3.0>nona-3,8-dien-7-one 
• 92773-20-1 2-carbethoxy-9-chloro-4-ethylbicyclo<4.3.0>nona-3,8-dien-7-one 
• 92773-21-2 2-carbethoxy-4-ethylbicyclo<4.3.0>non-3-en-7-one 
• 92773-26-7 2-carbethoxy-4-ethylbicyclo<4.3.0>non-3,8-dien-7-one 
• 92773-25-6 2-carboxy-4-ethylbicyclo<4.3.0>nona-3,8-dien-7-one 
• 92773-24-5 4-ethyl-2-hydroxymethylbicyclo<4.3.0>nona-3,8-dien-7-one 
• 930-60-9 maleic anhydride 
• 13369-25-0 ethyl 4-methylene-(2E)-hexenoate 
• 25404-15-3 4-cyclopentene-1,3-dione monoethylene ketal 
• 1187021-54-0 5-ethyl-3-hydroxy-2H-pyran-2-one 

Downstream Products

• 62251-96-1 (+)-coronatine 
• 189506-61-4 coronatine benzyl ester 
• 1187021-48-2 C₁₈H₂₅NO₄ 
• 73344-10-2 coronafacic acid-L-Ile 

Relevant articles and documents

Intramolecular 1,6-conjugate addition approach for construction of the hydrindane framework: Total synthesis of (±)-coronafacic acid

A new approach for the construction of the hydrindane framework has been achieved by intramolecular 1,6-conjugate addition under some basic conditions. The precursors, α, β, γ, δ-unsaturated esters (11a-11d) were synthesized from the ester 8 and acrolein derivatives (6a-6d) via aldol condensation. This methodology was applied to the total synthesis of (±)-coronafacic acid and its analogues.

Stereoselective Route to Functionalized cis-Hydrindanes from Tricyclo2,6>decan-10-ones. A Total Synthesis of (+/-)-Coronafacic Acid

A flexible approach to functionalized cis-hydrindanes via Haller-Bauer type cleavage of endo-tricyclo2,6>decan-10-ones is delineated and its efficacy demonstrated through a concise synthesis of (+/-)-coronafacic acid.

Synthesis of (+/-)-Coronafacic Acid. Efficient Intramolecular Diels-Alder Reaction of Latent Diene-Dienophile Functionality via Thermal Reaction

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Total Synthesis of (+/-)-Coronafacic Acid: Use of Anionic Oxy-Cope Rearrangements on Aromatic Substrates in Synthesis

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A scalable synthesis of (+)-coronafacic acid

A facile, efficient, and scalable synthesis of optically pure coronafacic acid by resolution of racemic coronafacic acid obtained using an improved version of Watson's method has been developed. By optimizing the boron-mediated aldol reaction of Watson, we were able to prepare 2.1 g of racemic coronafacic acid. This was coupled with (S)-4-isopropyl-2-oxazolidinone to give a mixture of diastereomeric coronafacyl oxazolidinones, which were readily separable by silica-gel column chromatography to give 630 mg of optically pure (+)-coronafacic acid.

Azido-coronatine: A useful platform for "click chemistry"- mediated probe synthesis for bioorganic studies

We report on the development of azide-coronatine as a useful platform for azide alkyne cycloaddition ("click chemistry")-mediated synthesis of molecular probes. (p)-Azido-coronatine was synthesized in 10 steps with 11% yield using improved synthesis of coronafacic acid, in which the highly exo-selective Diels-Alder reaction (endo:exo > 1:25) is the key step. Azido coronatine was as effective as the original coronatine in a stomatal opening assay, and was easily modified to a fluorescein isothiocyanate (FITC)-labeled probe with high yield.