(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