(4R,4aS,8aR)-4-(furan-3-yl)-3,4a,8,8-tetramethyl-8a-[(trimethylsilyl)oxy]-4a,5,6,7,8,8a-hexahydro-4H-1,2-benzoxazine 2-oxide

Base Information

• Chemical Name: (4R,4aS,8aR)-4-(furan-3-yl)-3,4a,8,8-tetramethyl-8a-[(trimethylsilyl)oxy]-4a,5,6,7,8,8a-hexahydro-4H-1,2-benzoxazine 2-oxide
• CAS No.: 124070-93-5
• Molecular Formula: C19H31 N O4 Si
• Molecular Weight: 365.5392
• Mol file: 124070-93-5.mol

Synonyms:4H-1,2-Benzoxazine,4-(3-furanyl)-4a,5,6,7,8,8a-hexahydro-3,4a,8,8-tetramethyl-8a-[(trimethylsilyl)oxy]-,2-oxide, (4a,4ab,8ab)- (9CI); 4H-1,2-Benzoxazine,4-(3-furanyl)-4a,5,6,7,8,8a-hexahydro-3,4a,8,8-tetramethyl-8a-[(trimethylsilyl)oxy]-,2-oxide, (4a,4ab,8ab)-(?à)-

Chemical Property of (4R,4aS,8aR)-4-(furan-3-yl)-3,4a,8,8-tetramethyl-8a-[(trimethylsilyl)oxy]-4a,5,6,7,8,8a-hexahydro-4H-1,2-benzoxazine 2-oxide

Chemical Property:

• Vapor Pressure: 1.95E-06mmHg at 25°C
• Boiling Point: 406.2°C at 760 mmHg
• Flash Point: 199.4°C
• Density: 1.08g/cm³

Purity/Quality:

85.0-99.8% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (4R,4aS,8aR)-4-(furan-3-yl)-3,4a,8,8-tetramethyl-8a-[(trimethylsilyl)oxy]-4a,5,6,7,8,8a-hexahydro-4H-1,2-benzoxazine 2-oxide

There total 1 articles about (4R,4aS,8aR)-4-(furan-3-yl)-3,4a,8,8-tetramethyl-8a-[(trimethylsilyl)oxy]-4a,5,6,7,8,8a-hexahydro-4H-1,2-benzoxazine 2-oxide 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: 57.0%

2,6,6-trimethyl-1-trimethylsilyloxycyclohexene (83999-44-4) + (E)-1-(3-furyl)-2-nitro-1-propene (124070-88-8,860003-90-3) → (1'RS,2SR)-2,6,6-trimethyl-2-<1'-(3-furyl)-2-oxopropyl>cyclohexanone (124070-94-6) + (4RS,4aSR)-4-(3-furyl)-3,4a,8,8-tetramethyl-8a-(trimethylsiloxy)-4a,5,6,7,8,8a-hexahydro-4H-1,2-benzoxazine N-oxide (124070-93-5)

Guidance literature:

With titanium tetrachloride; In dichloromethane; at -78 ℃; for 0.25h;

DOI:10.1021/jo00291a048

Reference yield:

(4RS,4aSR)-4-(3-furyl)-3,4a,8,8-tetramethyl-8a-(trimethylsiloxy)-4a,5,6,7,8,8a-hexahydro-4H-1,2-benzoxazine N-oxide (124070-93-5) → (1'RS,2SR)-2,6,6-trimethyl-2-<1'-(3-furyl)-2-oxopropyl>cyclohexanone (124070-94-6)

Guidance literature:

With titanium(III) chloride; In tetrahydrofuran; for 10h; Ambient temperature;

DOI:10.1021/jo00291a048

Reference yield:

(4RS,4aSR)-4-(3-furyl)-3,4a,8,8-tetramethyl-8a-(trimethylsiloxy)-4a,5,6,7,8,8a-hexahydro-4H-1,2-benzoxazine N-oxide (124070-93-5) → (1RS,2RS,3RS,3aSR,7aSR)-1-(3-furyl)-4,4,7a-trimethyl-3,3a-epoxyhexahydroindan-2-ol (124070-97-9)

Guidance literature:

Multi-step reaction with 4 steps

1: aq. TiCl₃ / tetrahydrofuran / 10 h / Ambient temperature

2: 64 percent / KOH / ethanol / 0.67 h / Heating

3: 97 percent / LiAlH₄ / diethyl ether / 3 h / 0 °C

4: 75 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 3 h / -40 °C

With potassium hydroxide; lithium aluminium tetrahydride; titanium(III) chloride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane;

DOI:10.1021/jo00291a048

upstream raw materials:

2,6,6-trimethyl-1-trimethylsilyloxycyclohexene

(E)-1-(3-furyl)-2-nitro-1-propene

Downstream raw materials:

(1'RS,2SR)-2,6,6-trimethyl-2-<1'-(3-furyl)-2-oxopropyl>cyclohexanone

(1RS,3SR,3aSR,7aSR)-1-(3-furyl)-4,4,7a-trimethyl-3,3a-epoxyhexahydro-indan-2-one

(1RS,2RS,3RS,3aSR,7aSR)-1-(3-furyl)-4,4,7a-trimethyl-3,3a-epoxyhexahydroindan-2-ol

(1RS,2RS,7aSR)-1-(3-furyl)-4,4,7a-trimethyl-1,4,5,6,7,7a-hexahydro-2H-inden-2-ol