(3R)-3,4,5,6,6aα,7,8,9-Octahydro-2,2,6α,9β-tetramethyl-3,9aβ-methano-2H-cyclopent[b]oxocin

Base Information

• Chemical Name: (3R)-3,4,5,6,6aα,7,8,9-Octahydro-2,2,6α,9β-tetramethyl-3,9aβ-methano-2H-cyclopent[b]oxocin
• CAS No.: 21764-22-7
• Molecular Formula: C15H26O
• Molecular Weight: 222.37
• Mol file: 21764-22-7.mol

Synonyms:(1S,2R,5R,6S,9R)-2,6,10,10-Tetramethyl-11-oxa-tricyclo[7.2.1.01,5]dodecane;Liguloxid;

Chemical Property of (3R)-3,4,5,6,6aα,7,8,9-Octahydro-2,2,6α,9β-tetramethyl-3,9aβ-methano-2H-cyclopent[b]oxocin

Chemical Property:

• Melting Point: 36 °C
• Boiling Point: 262.9±8.0 °C(Predicted)
• PSA: 9.23000
• Density: 0.97±0.1 g/cm3(Predicted)
• LogP: 4.01630

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (3R)-3,4,5,6,6aα,7,8,9-Octahydro-2,2,6α,9β-tetramethyl-3,9aβ-methano-2H-cyclopent[b]oxocin

There total 24 articles about (3R)-3,4,5,6,6aα,7,8,9-Octahydro-2,2,6α,9β-tetramethyl-3,9aβ-methano-2H-cyclopent[b]oxocin 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:

3,7-dimethyloct-6-en-1-yn-3-ol (29171-20-8) → (+/-)-liguloxide (15415-06-2,18680-77-8,18680-81-4,20149-50-2,21764-22-7,29701-69-7,33784-90-6,59432-93-8,59432-94-9,145512-08-9,145514-33-6)

Guidance literature:

Multi-step reaction with 10 steps

1: 95 percent / phenol / 48 h / 140 °C

2: 92 percent / aq.KOH / tetrahydrofuran / 2 h / 90 °C

3: 1) I₂, aq.NaHCO₃ / 1) ether, 0 deg C, 2) Bu₃SnH, AIBN, benzene, reflux

4: 1) LDA / 1) THF, -78 deg C, 30 min, 2) 20 min

5: SnCl₄, NaHCO₃ / CH₂Cl₂ / 0.5 h / 0 °C

7: Bu₃SnH, AIBN / benzene / 8 h / Heating

8: diethyl ether / 1) 0 deg C, 20 min, 2) r.t., 1 h

9: 62 percent / MsCl, pyridine / 1) 0 deg C, 10 min, 2) r.t., 6 h (procedure repeated)

10: H₂, HOAc / PtO₂ / ethyl acetate / 4 h / Ambient temperature

With pyridine; potassium hydroxide; 2,2'-azobis(isobutyronitrile); hydrogen; iodine; tri-n-butyl-tin hydride; tin(IV) chloride; sodium hydrogencarbonate; acetic acid; methanesulfonyl chloride; lithium diisopropyl amide; phenol; platinum(IV) oxide; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; benzene;

DOI:10.1016/S0040-4039(00)61015-8

Reference yield:

3,7-dimethyloct-6-en-1-yn-3-ol (29171-20-8) → (+/-)-10-epiliguloxide (15415-06-2,18680-77-8,18680-81-4,20149-50-2,21764-22-7,29701-69-7,33784-90-6,59432-93-8,59432-94-9,145512-08-9,145514-33-6)

Guidance literature:

Multi-step reaction with 10 steps

1: 95 percent / phenol / 48 h / 140 °C

2: 92 percent / aq.KOH / tetrahydrofuran / 2 h / 90 °C

3: 1) I₂, aq.NaHCO₃ / 1) ether, 0 deg C, 2) Bu₃SnH, AIBN, benzene, reflux

4: 1) LDA / 1) THF, -78 deg C, 30 min, 2) 20 min

5: SnCl₄, NaHCO₃ / CH₂Cl₂ / 0.5 h / 0 °C

7: Bu₃SnH, AIBN / benzene / 8 h / Heating

8: diethyl ether / 1) 0 deg C, 20 min, 2) r.t., 1 h

9: 62 percent / MsCl, pyridine / 1) 0 deg C, 10 min, 2) r.t., 6 h (procedure repeated)

10: H₂, HOAc / PtO₂ / ethyl acetate / 4 h / Ambient temperature

With pyridine; potassium hydroxide; 2,2'-azobis(isobutyronitrile); hydrogen; iodine; tri-n-butyl-tin hydride; tin(IV) chloride; sodium hydrogencarbonate; acetic acid; methanesulfonyl chloride; lithium diisopropyl amide; phenol; platinum(IV) oxide; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; benzene;

DOI:10.1016/S0040-4039(00)61015-8

Reference yield:

2-(2-carboxyethyl)-3-isopropenyl-1-methyl-cyclopent-1-ene (49748-18-7) → (+/-)-liguloxide (15415-06-2,18680-77-8,18680-81-4,20149-50-2,21764-22-7,29701-69-7,33784-90-6,59432-93-8,59432-94-9,145512-08-9,145514-33-6)

Guidance literature:

Multi-step reaction with 8 steps

1: 1) I₂, aq.NaHCO₃ / 1) ether, 0 deg C, 2) Bu₃SnH, AIBN, benzene, reflux

2: 1) LDA / 1) THF, -78 deg C, 30 min, 2) 20 min

3: SnCl₄, NaHCO₃ / CH₂Cl₂ / 0.5 h / 0 °C

5: Bu₃SnH, AIBN / benzene / 8 h / Heating

6: diethyl ether / 1) 0 deg C, 20 min, 2) r.t., 1 h

7: 62 percent / MsCl, pyridine / 1) 0 deg C, 10 min, 2) r.t., 6 h (procedure repeated)

8: H₂, HOAc / PtO₂ / ethyl acetate / 4 h / Ambient temperature

With pyridine; 2,2'-azobis(isobutyronitrile); hydrogen; iodine; tri-n-butyl-tin hydride; tin(IV) chloride; sodium hydrogencarbonate; acetic acid; methanesulfonyl chloride; lithium diisopropyl amide; platinum(IV) oxide; In diethyl ether; dichloromethane; ethyl acetate; benzene;

DOI:10.1016/S0040-4039(00)61015-8

upstream raw materials:

(1S,2R,5R,9R)-2,10,10-Trimethyl-6-methylene-11-oxa-tricyclo[7.2.1.0^1,5]dodecane

3,7-dimethyloct-6-en-1-yn-3-ol

2-(2-carboxyethyl)-3-isopropenyl-1-methyl-cyclopent-1-ene

6-Isopropenyl-9-methyl-1-oxa-spiro[4.4]nonan-2-one

Refernces

STUDIES ON SESQUITERPENOID OXIDES-XIX: STRUCTURE AND ABSOLUTE CONFIGURATION OF LIGULOXIDE, LIGULOXIDOL AND LIGULOXIDOL ACETATE

10.1016/S0040-4020(01)92870-4

The study focuses on the isolation and structural elucidation of three sesquiterpene oxides, namely liguloxide (III), liguloxidol (IV), and liguloxidol acetate (V), from the aerial parts of Ligularia turczaninowii. The researchers used various chemical reactions and analytical techniques to determine the structure and absolute configuration of these compounds. They employed microbial hydroxylation to introduce hydroxyl groups into the molecule, aiding in structural determination. Liguloxide was found to be a guaiane sesquiterpene with a ditertiary ether bridge, while liguloxidol and liguloxidol acetate were shown to have the same framework with an additional hydroxyl group. The study also involved the preparation of various epimers and the use of osmium tetroxide oxidation, Jones oxidation, and other reactions to confirm the structure and configuration of these compounds. The absolute configuration was clarified by correlating liguloxide with the known compound guaioxide (XIX) through epimerization of the C-4 methyl group and microbial hydroxylation.