(6aS,10aR)-7,9-dimethyl-6,6a,8,10a-tetrahydro-4H-indolo[4,3-fg]quinoline

Base Information

• Chemical Name: (6aS,10aR)-7,9-dimethyl-6,6a,8,10a-tetrahydro-4H-indolo[4,3-fg]quinoline
• CAS No.: 548-42-5
• Molecular Formula: C16H18 N2
• Molecular Weight: 238.332
• Hs Code.: 2933990090
• European Community (EC) Number: 208-947-3
• Nikkaji Number: J359.617F
• Wikipedia: Agroclavine
• Mol file: 548-42-5.mol

Synonyms:AGROCLAVIN;548-42-5;(5alpha)-8,9-Didehydro-6,8-dimethylergoline;194346-16-2

Chemical Property of (6aS,10aR)-7,9-dimethyl-6,6a,8,10a-tetrahydro-4H-indolo[4,3-fg]quinoline

Chemical Property:

• Vapor Pressure: 2.4E-07mmHg at 25°C
• Melting Point: 198-208℃ (decomposition) (ethyl ether )
• Refractive Index: 1.5000 (estimate)
• Boiling Point: 422.5°Cat760mmHg
• PKA: 17.49±0.40(Predicted)
• Flash Point: 209.3°C
• PSA: 19.03000
• Density: 1.161g/cm³
• LogP: 3.00580
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 238.146998583
• Heavy Atom Count: 18
• Complexity: 375

Purity/Quality:

99%min ^*data from raw suppliers

Agroclavine ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC2C(CC3=CNC4=CC=CC2=C34)N(C1)C
• Isomeric SMILES: CC1=C[C@H]2[C@H](CC3=CNC4=CC=CC2=C34)N(C1)C
• Uses: Agroclavine is an ergot alkaloid and a fungal metabolite. It is also an environmental and food contaminant.

Technology Process of (6aS,10aR)-7,9-dimethyl-6,6a,8,10a-tetrahydro-4H-indolo[4,3-fg]quinoline

There total 47 articles about (6aS,10aR)-7,9-dimethyl-6,6a,8,10a-tetrahydro-4H-indolo[4,3-fg]quinoline 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: 90.0%

Isochanoclavin-(I) (1150-44-3,11012-16-1) → agroclavine (548-42-5,194346-16-2)

Guidance literature:

With potassium carbonate; trichlorophosphate; In acetonitrile;

DOI:10.3987/COM-97-7821

Reference yield: 52.0%

HCl salt of N-p-Ts lysergene (120408-46-0) → agroclavine (548-42-5,194346-16-2)

Guidance literature:

ammonia; lithium;

DOI:10.1016/S0040-4039(00)84824-8

Reference yield:

Indole-3-carboxaldehyde (487-89-8,1228547-52-1) → agroclavine (548-42-5,194346-16-2)

Guidance literature:

Multi-step reaction with 12 steps

1: dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver hexafluoroantimonate; copper diacetate / 4 h / 110 °C / Inert atmosphere

2: dmap / acetonitrile / 0.5 h / 40 °C

3: ammonium acetate / 2 h / 70 °C

4: diisobutylaluminium hydride / tetrahydrofuran; hexane / 1 h / -78 °C

5: sodium tetrahydroborate / tetrahydrofuran; methanol / 1 h / 20 °C

6: triethylamine / dichloromethane / 1 h / 0 - 20 °C

7: potassium carbonate; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); palladium diacetate / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere

8: hydrogenchloride; zinc / methanol; water / 1 h

9: potassium carbonate / acetonitrile / 20 h / 20 °C

10: triethylamine / dichloromethane / 24 h / 20 °C

11: 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(iso-propoxy)-5-(N,N-dimethylaminosulfonyl)phenyl]methylene ruthenium(II) dichloride / toluene / 12 h / 80 °C / Inert atmosphere

12: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / Reflux

With hydrogenchloride; dmap; sodium tetrahydroborate; silver hexafluoroantimonate; lithium aluminium tetrahydride; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(iso-propoxy)-5-(N,N-dimethylaminosulfonyl)phenyl]methylene ruthenium(II) dichloride; ammonium acetate; copper diacetate; palladium diacetate; diisobutylaluminium hydride; potassium carbonate; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); triethylamine; zinc; In tetrahydrofuran; methanol; hexane; dichloromethane; water; toluene; acetonitrile;

DOI:10.1021/acs.orglett.7b01681

upstream raw materials:

elymoclavine

L-Tryptophan

Lysergen

HCl salt of N-p-Ts lysergene

Downstream raw materials:

C₃₇H₃₈N₂O₅

C₃₇H₃₈N₂O₅

elymoclavine

1-methyl-agroclavine

Refernces

• 1、 Lv, Jianbo,Wang, Bin,Yuan, Kuo,Wang, Yuan,Jia, Yanxing. "Regioselective Direct C-4 Functionalization of Indole: Total Syntheses of (-)-Agroclavine and (-)-Elymoclavine". . p. 3664 - 3667. Retrieved 2017/07/15.
• 2、 Cheng, Johnathan Z.,Coyle, Christine M.,Panaccione, Daniel G.,O'Connor, Sarah E.. "Controlling a structural branch point in ergot alkaloid biosynthesis". supporting information; experimental part. p. 12835 - 12837. Retrieved 2010/11/05.