Coronafacic acid

Base Information

• Chemical Name: Coronafacic acid
• CAS No.: 62251-98-3
• Molecular Formula: C12H16O3
• Molecular Weight: 208.25364
• Hs Code.: 2918300090
• DSSTox Substance ID: DTXSID80977827
• Nikkaji Number: J53.003D
• Wikidata: Q27149241
• Metabolomics Workbench ID: 105550
• Mol file: 62251-98-3.mol

Synonyms:coronafacic acid

Chemical Property of Coronafacic acid

Chemical Property:

• Vapor Pressure: 1.14E-06mmHg at 25°C
• Boiling Point: 375.4°C at 760 mmHg
• Flash Point: 195°C
• PSA: 54.37000
• Density: 1.168g/cm³
• LogP: 2.02260
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 208.109944368
• Heavy Atom Count: 15
• Complexity: 330

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1CC2C(CCC2=O)C(=C1)C(=O)O
• Isomeric SMILES: CC[C@@H]1C[C@H]2[C@H](CCC2=O)C(=C1)C(=O)O

Technology Process of Coronafacic acid

There total 191 articles about Coronafacic 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: 100.0%

(3aS,6R,7aS)-methyl 6-ethyl-1-oxo-2,3,3a,6,7,7a-hexahydro-1H-indene-4-carboxylate (87335-70-4) → (+)-coronafacic acid (62251-98-3)

Guidance literature:

With hydrogenchloride; water; for 6h; Reflux;

DOI:10.1002/open.202000210

Reference yield: 99.0%

methyl rel-(1S,4R,6S)-4-ethyl-7-oxo-bicyclo[4.3.0]-non-2-ene-2-carboxylate (62252-00-0,73961-72-5,87335-70-4) → (+/-)-(3a,6-trans; 3a,7a-cis)-6-ethyl-4-(hydroxymethyl)-2,3,3a,6,7,7a-hexahydro-1H-indene-4-carboxylate (62251-98-3,62251-99-4,66322-23-4,87335-74-8,92843-35-1)

Guidance literature:

With hydrogenchloride; water; for 10h; Reflux;

DOI:10.1039/b905159g

Reference yield: 95.0%

ethyl 6-ethyl-1-oxo-2,3,3a,6,7,7a-hexahydro-1H-indene-4-carboxylate (79405-48-4,79405-49-5) → (+/-)-(3a,6-trans; 3a,7a-cis)-6-ethyl-4-(hydroxymethyl)-2,3,3a,6,7,7a-hexahydro-1H-indene-4-carboxylate (62251-98-3,62251-99-4,66322-23-4,87335-74-8,92843-35-1)

Guidance literature:

With hydrogenchloride; for 4h; Heating;

DOI:10.1016/S0040-4020(97)00614-5

upstream raw materials:

(3aS,6R,7aS)-methyl 6-ethyl-1-oxo-2,3,3a,6,7,7a-hexahydro-1H-indene-4-carboxylate

(+)-coronatine

(3aS,6R,7aS)-ethyl 6-ethyl-1-oxo-2,3,3a,6,7,7a-hexahydro-1H-indene-4-carboxylate

Methyl (1S,4R,6S)-4-ethylspiro(bicyclo[4.3.0]non-2-ene-7,2'-[1,3]dioxolane)-2-carboxylate

Downstream raw materials:

coronatine benzyl ester

(+)-coronatine

C₁₈H₂₅NO₄

coronafacic acid-L-Ile

Refernces

• 1、 Toshima, Hiroaki,Nara, Shinji,Ichihara, Akitami,Koda, Yasunori,Kikuta, Yoshio. "Syntheses and Potato Tuber-inducing Activity of Coronafacic Acid Analogues". . p. 681 - 688. Retrieved 1998.
• 2、 Liu,Llinas-Brunet. "Total synthesis of d,l-coronafacic acid by an intermolecular Diels-Alder approach". . p. 1747 - 1750. Retrieved 1984.
• 3、 Hayashi, Kengo,Kato, Nobuki,Kuwahara, Shigefumi,Ogura, Yusuke,Tozawa, Sho,Ueda, Minoru,Watanabe, Raku. "Stereoselective Syntheses of all the Possible Stereoisomers of Coronafacic Acid". . p. 1008 - 1017. Retrieved 2020.
• 4、 Cai, Quan,Chen, Xiangyang,Houk, K. N.,Lu, Qi-Tao,Tan, Kui,Xu, Meng-Meng,Yang, Limin. "An enantioselective ambimodal cross-Diels–Alder reaction and applications in synthesis". . p. 892 - 900. Retrieved 2021/10/20.
• 5、 Kosaki, Yusuke,Ogawa, Narihito,Wang, Qian,Kobayashi, Yuichi. "Synthesis of coronafacic acid via TBAF-assisted elimination of the mesylate and its conversion to the isoleucine conjugate". supporting information; experimental part. p. 4232 - 4235. Retrieved 2011/10/09.