diisocyanoadociane

Base Information

• Chemical Name: diisocyanoadociane
• CAS No.: 60197-58-2
• Molecular Formula: C₂₂H₃₂N₂
• Molecular Weight: 324.509
• Mol file: 60197-58-2.mol

Synonyms:diisocyanoadociane

Chemical Property of diisocyanoadociane

Chemical Property:

• PSA: 0.00000
• LogP: 4.16820

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of diisocyanoadociane

There total 12 articles about diisocyanoadociane 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:

trimethylsilyl cyanide (7677-24-9) + C24H32F6O4 → 7,20-diisocyanoadociane + (+)-7,20-diisocyanoadociane (60197-58-2,84788-24-9)

Guidance literature:

With scandium tris(trifluoromethanesulfonate); In neat (no solvent); at 20 ℃; for 7h; Overall yield = 4.7 mg; diastereoselective reaction; Inert atmosphere;

DOI:10.1021/jacs.6b03899

Reference yield:

methyl (R)-2-methyl-3-(1-methyl-4,7-dioxo-2,3a1,4,5,6,6a,7,8,9,9adecahydro-1H-phenalen-3-yl)propanoate → 7,20-diisocyanoadociane + (+)-7,20-diisocyanoadociane (60197-58-2,84788-24-9)

Guidance literature:

Multi-step reaction with 11 steps

1.1: methoxybenzene / toluene; dichloromethane; 2-methyltetrahydrofuran / -78 - -40 °C / Inert atmosphere

2.1: manganese(III) (Z)-2,2,6,6-tetramethyl-5-oxohept-3-en-3-olate; tert.-butylhydroperoxide; phenylsilane / isopropyl alcohol / 8 h / 20 °C / Inert atmosphere

3.1: diisobutylaluminium hydride / hexane; tetrahydrofuran / 2 h / -78 - 0 °C / Inert atmosphere

4.1: Dess-Martin periodane / dichloromethane / 0.75 h / 22 °C / Inert atmosphere

5.1: 2-pentafluorophenyl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate; caesium carbonate / 1,2-dichloro-ethane / 24 h / 80 °C / Inert atmosphere

6.1: samarium diiodide / tetrahydrofuran; methanol / 0.25 h / 22 °C / Inert atmosphere

7.1: cerium(III) chloride / tetrahydrofuran; pentane / -78 °C / Inert atmosphere

7.2: 1.17 h / -78 - 0 °C / Inert atmosphere

7.3: 0.25 h / -78 °C / Inert atmosphere

8.1: hydrogen fluoride / water; acetonitrile / 2 h / 20 °C / Inert atmosphere

9.1: mercury(II) diacetate / tetrahydrofuran; water / 0.33 h / 20 °C / Inert atmosphere

9.2: 20 °C / Inert atmosphere

10.1: pyridine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

11.1: scandium tris(trifluoromethanesulfonate) / neat (no solvent) / 7 h / 20 °C / Inert atmosphere

With 2-pentafluorophenyl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate; pyridine; tert.-butylhydroperoxide; samarium diiodide; cerium(III) chloride; manganese(III) (Z)-2,2,6,6-tetramethyl-5-oxohept-3-en-3-olate; phenylsilane; hydrogen fluoride; mercury(II) diacetate; diisobutylaluminium hydride; caesium carbonate; Dess-Martin periodane; methoxybenzene; scandium tris(trifluoromethanesulfonate); In tetrahydrofuran; 2-methyltetrahydrofuran; methanol; hexane; dichloromethane; water; 1,2-dichloro-ethane; isopropyl alcohol; toluene; acetonitrile; pentane;

DOI:10.1021/jacs.6b03899

Reference yield:

methyl (R)-3-((1S,6aS,7R,9aR,9bR)-7-hydroxy-1,7-dimethyl-4-oxo-2,3a1,4,5,6,6a,7,8,9,9a-decahydro-1H-phenalen-3-yl)-2-methylpropanoate → 7,20-diisocyanoadociane + (+)-7,20-diisocyanoadociane (60197-58-2,84788-24-9)

Guidance literature:

Multi-step reaction with 10 steps

1.1: manganese(III) (Z)-2,2,6,6-tetramethyl-5-oxohept-3-en-3-olate; tert.-butylhydroperoxide; phenylsilane / isopropyl alcohol / 8 h / 20 °C / Inert atmosphere

2.1: diisobutylaluminium hydride / hexane; tetrahydrofuran / 2 h / -78 - 0 °C / Inert atmosphere

3.1: Dess-Martin periodane / dichloromethane / 0.75 h / 22 °C / Inert atmosphere

4.1: 2-pentafluorophenyl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate; caesium carbonate / 1,2-dichloro-ethane / 24 h / 80 °C / Inert atmosphere

5.1: samarium diiodide / tetrahydrofuran; methanol / 0.25 h / 22 °C / Inert atmosphere

6.1: cerium(III) chloride / tetrahydrofuran; pentane / -78 °C / Inert atmosphere

6.2: 1.17 h / -78 - 0 °C / Inert atmosphere

6.3: 0.25 h / -78 °C / Inert atmosphere

7.1: hydrogen fluoride / water; acetonitrile / 2 h / 20 °C / Inert atmosphere

8.1: mercury(II) diacetate / tetrahydrofuran; water / 0.33 h / 20 °C / Inert atmosphere

8.2: 20 °C / Inert atmosphere

9.1: pyridine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

10.1: scandium tris(trifluoromethanesulfonate) / neat (no solvent) / 7 h / 20 °C / Inert atmosphere

With 2-pentafluorophenyl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate; pyridine; tert.-butylhydroperoxide; samarium diiodide; cerium(III) chloride; manganese(III) (Z)-2,2,6,6-tetramethyl-5-oxohept-3-en-3-olate; phenylsilane; hydrogen fluoride; mercury(II) diacetate; diisobutylaluminium hydride; caesium carbonate; Dess-Martin periodane; scandium tris(trifluoromethanesulfonate); In tetrahydrofuran; methanol; hexane; dichloromethane; water; 1,2-dichloro-ethane; isopropyl alcohol; acetonitrile; pentane;

DOI:10.1021/jacs.6b03899

upstream raw materials:

trimethylsilyl cyanide

Downstream raw materials:

1-(3-Chloro-phenyl)-3-{(1R,2R,3aS,5S,5aR,8S,8aS,10aS,10bS,10cS)-8-[3-(3-chloro-phenyl)-ureido]-1,2,5,8-tetramethyl-hexadecahydro-pyren-1-yl}-urea

N-{(1R,2R,3aS,5S,5aR,8S,8aS,10aS,10bS,10cS)-8-[3-(4-Bromo-phenyl)-thioureido]-1,2,5,8-tetramethyl-hexadecahydro-pyren-1-yl}-formamide

N-{(1R,2R,3aS,5S,5aR,8S,8aS,10aS,10bS,10cS)-8-[3-(3-Chloro-phenyl)-ureido]-1,2,5,8-tetramethyl-hexadecahydro-pyren-1-yl}-formamide

4-Bromo-N-((1S,3aR,4S,5aS,7R,8R,8aS,10aS,10bS,10cS)-8-formylamino-1,4,7,8-tetramethyl-hexadecahydro-pyren-1-yl)-benzamide

Refernces

• 1、 Lu, Hai-Hua,Pronin, Sergey V.,Antonova-Koch, Yevgeniya,Meister, Stephan,Winzeler, Elizabeth A.,Shenvi, Ryan A.. "Synthesis of (+)-7,20-Diisocyanoadociane and Liver-Stage Antiplasmodial Activity of the Isocyanoterpene Class". . p. 7268 - 7271. Retrieved 2016.