(-)-trans-Clavicipitic acid

Base Information

• Chemical Name: (-)-trans-Clavicipitic acid
• CAS No.: 33062-26-9
• Molecular Formula: C₁₆H₁₈N₂O₂
• Molecular Weight: 270.331
• UNII: 374VHV303R,34R1382X09
• Nikkaji Number: J19.297J
• Wikidata: Q27121118
• Metabolomics Workbench ID: 56921
• Mol file: 33062-26-9.mol

Synonyms:(-)-trans-clavicipitic acid;Clavicipitic-acid;(+/-)-Clavicipitic acid I;Clavicipitic acid I;33062-26-9;trans-Clavicipitic acid;374VHV303R;Clavicipitic acid, trans-(+/-)-;(4S,6R)-clavicipitic acid;UNII-374VHV303R;Clavicipitic acid, trans-(-)-;34R1382X09;1H-Pyrrolo(4,3,2-ef)(2)benzazepine-4-carboxylic acid, 3,4,5,6-tetrahydro-6-(2-methyl-1-propen-1-yl)-, (4R,6S)-rel-;84986-03-8;Rel-(4R,6S)-3,4,5,6-tetrahydro-6-(2-methyl-1-propen-1-yl)-1H-pyrrolo(4,3,2-ef)(2)benzazepine-4-carboxylic acid;(4S,6R)-3,4,5,6-Tetrahydro-6-(2-methyl-1-propen-1-yl)-1H-pyrrolo(4,3,2-ef)(2)benzazepine-4-carboxylic acid;(4S,6R)-6-(2-methylprop-1-en-1-yl)-3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd]indole-4-carboxylic acid;(9R,11S)-9-(2-methylprop-1-enyl)-3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraene-11-carboxylic acid;1H-Azepino(5,4,3-cd)indole-4-carboxylic acid, 3,4,5,6-tetrahydro-6-(2-methyl-1-propenyl)-, (4S-trans)-;1H-Pyrrolo(4,3,2-ef)(2)benzazepine-4-carboxylic acid, 3,4,5,6-tetrahydro-6-(2-methyl-1-propen-1-yl)-, (4S,6R)-;trans-(+/-)-clavicipitic acid;CHEBI:48270;UNII-34R1382X09;Q27121118

Chemical Property of (-)-trans-Clavicipitic acid

Chemical Property:

• PSA: 61.69000
• LogP: 2.20700
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 270.136827821
• Heavy Atom Count: 20
• Complexity: 417

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CC1C2=C3C(=CNC3=CC=C2)CC(N1)C(=O)O)C
• Isomeric SMILES: CC(=C[C@@H]1C2=C3C(=CNC3=CC=C2)C[C@H](N1)C(=O)O)C

Technology Process of (-)-trans-Clavicipitic acid

There total 96 articles about (-)-trans-Clavicipitic 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%

methyl (4S,6R)-1-(t-butoxycarbonyl)-3,4,5,6-tetrahydro-6-(2-methyl-1-propenyl)azepino[5,4,3-cd]indole-4-carboxylate (250333-39-2) → (-)-trans-clavicipitic acid (33062-26-9)

Guidance literature:

With water; potassium carbonate; In methanol; for 48h; Reflux;

DOI:10.1021/jo9012755

Reference yield: 90.0%

6-(2-methyl-propenyl)-3,4,5,6-tetrahydro-azepino[5.4.3-cd]indole-1,4-dicarboxylic acid di-tert-butyl ester (956469-23-1) → (-)-trans-clavicipitic acid (33062-26-9)

Guidance literature:

With zinc dibromide; In dichloromethane; at 20 ℃; for 6h;

DOI:10.1021/jo071162h

Reference yield: 81.0%

cis-methyl 1-(2-methylprop-1-enyl)-2,3,4,6-tetrahydro-1H-azepino[5,4,3-cd]indole-3-carboxylate (65600-90-0,88315-34-8,88315-35-9) → (+/-)-4,6-cis-clavicipitic acid (33062-26-9,72690-85-8,84986-03-8,84986-04-9)

Guidance literature:

With potassium hydroxide; In methanol; water; at 20 ℃; for 0.75h;

DOI:10.1021/jo500245s

upstream raw materials:

dimethyl 1-carbethoxy-3,4,5,6-tetrahydro-6-(2-methyl-1-propenyl)azepino<5,4,3-cd>indole-4,4-dicarboxylate

methyl (4S,6R)-3,4,5,6-tetrahydro-6-(2-methyl-1-propenyl)-1H-azepino[5,4,3-cd]indole-4-carboxylate

6-(2-methyl-propenyl)-3,4,5,6-tetrahydro-azepino[5.4.3-cd]indole-1,4-dicarboxylic acid di-tert-butyl ester

(S,E)-tert-butyl 3-(2-amino-3-tert-butoxy-3-oxopropyl)-4-(3-hydroxy-3-methylbut-1-enyl)-1H-indole-1-carboxylate

Downstream raw materials:

(-)-aurantioclavine

Refernces

• 1、 Xu, Zhengren,Li, Qingjiang,Zhang, Lihe,Jia, Yanxing. "Efficient total synthesis of (-)-cis-clavicipitic acid". . p. 6859 - 6862. Retrieved 2009.
• 2、 Chein, Rong-Jie,Chen, Kuan-Lin,Lai, Chen-Yu,Lin, Hsiao-Ching,Pham, Mai-Truc,Tang, Yi. "Enzyme-Catalyzed Azepinoindole Formation in Clavine Alkaloid Biosynthesis". . . Retrieved 2020.
• 3、 Bartoccini, Francesca,Casoli, Mariangela,Mari, Michele,Piersanti, Giovanni. "Synthesis of (±)- cis -clavicipitic acid by a Rh(I)-catalyzed intramolecular imine reaction". . p. 3255 - 3259. Retrieved 2014/05/06.