(4R,5S,6R)-3-methyl-4-phenyl-5-(2-propenyl)-6-[(1R,2S)-(2-phenylcyclohexyl)oxy]-5,6-dihydro-4H-[1,2]-oxazine 2-oxide

Base Information

• Chemical Name: (4R,5S,6R)-3-methyl-4-phenyl-5-(2-propenyl)-6-[(1R,2S)-(2-phenylcyclohexyl)oxy]-5,6-dihydro-4H-[1,2]-oxazine 2-oxide
• CAS No.: 213695-92-2
• Molecular Formula: C₂₆H₃₁NO₃
• Molecular Weight: 405.537

Synonyms:(4R,5S,6R)-3-methyl-4-phenyl-5-(2-propenyl)-6-[(1R,2S)-(2-phenylcyclohexyl)oxy]-5,6-dihydro-4H-[1,2]-oxazine 2-oxide

Chemical Property of (4R,5S,6R)-3-methyl-4-phenyl-5-(2-propenyl)-6-[(1R,2S)-(2-phenylcyclohexyl)oxy]-5,6-dihydro-4H-[1,2]-oxazine 2-oxide

Chemical Property:

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Technology Process of (4R,5S,6R)-3-methyl-4-phenyl-5-(2-propenyl)-6-[(1R,2S)-(2-phenylcyclohexyl)oxy]-5,6-dihydro-4H-[1,2]-oxazine 2-oxide

There total 4 articles about (4R,5S,6R)-3-methyl-4-phenyl-5-(2-propenyl)-6-[(1R,2S)-(2-phenylcyclohexyl)oxy]-5,6-dihydro-4H-[1,2]-oxazine 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: 0.047%

1-phenyl-2-nitroprop-1-ene (705-60-2,18315-84-9,58321-79-2) + {(1S,2R)-2-[((Z)-Penta-1,4-dienyl)oxy]-cyclohexyl}-benzene (213695-86-4) → (4S,5R,6S)-3-methyl-4-phenyl-5-(2-propenyl)-6-[(1R,2S)-(2-phenylcyclohexyl)oxy]-5,6-dihydro-4H-[1,2]-oxazine 2-oxide (213696-16-3) + (4R,5S,6R)-3-methyl-4-phenyl-5-(2-propenyl)-6-[(1R,2S)-(2-phenylcyclohexyl)oxy]-5,6-dihydro-4H-[1,2]-oxazine 2-oxide (213695-92-2)

Guidance literature:

With (1,1';3',1''-terphenyl)-2'-ol; trimethylaluminum; Yield given. Multistep reaction. Yields of byproduct given; 1.) toluene, room temperature, 40 min, 2.) CH₂Cl₂, -78 deg C to -35 deg C, 30 min; -35 deg C, 6 h;

DOI:10.1021/jo9802170

Reference yield:

1-phenyl-2-nitroprop-1-ene (705-60-2,18315-84-9,58321-79-2) + {(1S,2R)-2-[((E)-Penta-1,4-dienyl)oxy]-cyclohexyl}-benzene (197578-80-6) → (4S,5S,6S)-3-methyl-4-phenyl-5-(2-propenyl)-6-[(1R,2S)-(2-phenylcyclohexyl)oxy]-5,6-dihydro-4H-[1,2]-oxazine 2-oxide + (4R,5R,6R)-3-methyl-4-phenyl-5-(2-propenyl)-6-[(1R,2S)-(2-phenylcyclohexyl)oxy]-5,6-dihydro-4H-[1,2]-oxazine 2-oxide (197578-81-7) + (4R,5S,6S)-5-Allyl-3-methyl-4-phenyl-6-((1R,2S)-2-phenyl-cyclohexyloxy)-5,6-dihydro-4H-[1,2]oxazine 2-oxide + (4R,5S,6R)-3-methyl-4-phenyl-5-(2-propenyl)-6-[(1R,2S)-(2-phenylcyclohexyl)oxy]-5,6-dihydro-4H-[1,2]-oxazine 2-oxide (213695-92-2)

Guidance literature:

With (1,1';3',1''-terphenyl)-2'-ol; trimethylaluminum; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; 1.) toluene, room temperature, 40 min, 2.) CH₂Cl₂, -78 deg C to -25 deg C, 1 h; -25 deg C, 4 h;

DOI:10.1021/jo9802170

Reference yield:

(1R,2S)-trans-2-phenylcyclohexanol (98919-68-7) → (4R,5S,6R)-3-methyl-4-phenyl-5-(2-propenyl)-6-[(1R,2S)-(2-phenylcyclohexyl)oxy]-5,6-dihydro-4H-[1,2]-oxazine 2-oxide (213695-92-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) KH, 3.) n-BuLi / 1.) THF, room temperature, 3 h, 2.) THF, -78 deg C; room temperature, 13 h, 3.) -78 deg C, -78 deg C to 0 deg C, 2.5 h; 0 deg C, 30 min, 4.) HMPA, -70 deg C to -50 deg C, 1 h; 0 deg C, 3 h

2: 85 percent / LiAlH₄ / tetrahydrofuran / 1.5 h / Heating

3: SnCl₄ / CH₂Cl₂ / 0.17 h / -78 °C

With lithium aluminium tetrahydride; n-butyllithium; tin(IV) chloride; potassium hydride; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo9802170

upstream raw materials:

1-phenyl-2-nitroprop-1-ene

{(1S,2R)-2-[((E)-Penta-1,4-dienyl)oxy]-cyclohexyl}-benzene

{(1S,2R)-2-[((Z)-Penta-1,4-dienyl)oxy]-cyclohexyl}-benzene

(1R,2S)-trans-2-phenylcyclohexanol

Downstream raw materials:

((1S,2R,3S,4R)-3-Amino-4-hydroxymethyl-3-methyl-2-phenyl-cyclopentyl)-methanol

(1R,6R,7S,8R,9S)-9-methyl-8-phenyl-6-[(1R,2S)-(2-phenylcyclohexyl)oxy]-4-aza-3,5-dioxatricyclo[5.2.1.0^4,9]decane

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