(E)-4-((1R,4R)-4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl)-but-3-en-2-one

Base Information

• Chemical Name: (E)-4-((1R,4R)-4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl)-but-3-en-2-one
• CAS No.: 76739-74-7
• Molecular Formula: C₁₃H₂₀O₂
• Molecular Weight: 208.301
• Mol file: 76739-74-7.mol

Synonyms:(E)-4-((1R,4R)-4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl)-but-3-en-2-one

Chemical Property of (E)-4-((1R,4R)-4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl)-but-3-en-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-4-((1R,4R)-4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl)-but-3-en-2-one

There total 13 articles about (E)-4-((1R,4R)-4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl)-but-3-en-2-one 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: 100.0%

C19H34O2Si (1354005-98-3) → (E)-4-((1R,4R)-4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl)-but-3-en-2-one (76739-74-7)

Guidance literature:

With pyridine; pyridine hydrogenfluoride; In tetrahydrofuran; at 40 ℃; for 5h;

DOI:10.1016/j.tetlet.2011.10.151

Reference yield:

(rac)-(E)-4-(4-hydroxy-2,6,6-trimethyl-2-cyclohexen-1-yl)-2,2-ethylenedioxy-3-butene (1200125-02-5) → (E)-4-((1R,4R)-4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl)-but-3-en-2-one (76739-74-7) + (E)-4-((1S,4R)-4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl)-but-3-en-2-one

Guidance literature:

With hydrogenchloride; In water; acetone; at 20 ℃; for 0.5h; Overall yield = 38 mg;

DOI:10.1021/jo500605c

Reference yield:

C21H30O3 → (E)-4-((1R,4R)-4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl)-but-3-en-2-one (76739-74-7)

Guidance literature:

Multi-step reaction with 8 steps

1.1: Dess-Martin periodane / dichloromethane / 1 h / 0 °C

2.1: borane-THF; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran / 6 h / -40 °C

3.1: sodium bis(2-methoxyethoxy)aluminium dihydride / 4 h / 40 °C

3.2: 12 h / -78 - 0 °C

4.1: 2,6-dimethylpyridine / dichloromethane / 0.17 h / 20 °C

5.1: palladium diacetate; triethylamine; tris-(o-tolyl)phosphine / water; acetonitrile / 1.5 h / 80 °C

6.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1.5 h / 0 °C / pH 7 / aq. phosphate buffer

7.1: manganese(IV) oxide / dichloromethane / 24 h / 40 °C

8.1: pyridine; pyridine hydrogenfluoride / tetrahydrofuran / 5 h / 40 °C

With pyridine; 2,6-dimethylpyridine; manganese(IV) oxide; borane-THF; palladium diacetate; Dess-Martin periodane; pyridine hydrogenfluoride; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; tris-(o-tolyl)phosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; dichloromethane; water; acetonitrile; 5.1: Heck reaction;

DOI:10.1016/j.tetlet.2011.10.151

upstream raw materials:

C₂₇H₄₄O₃Si

C₁₆H₂₄O₃

C₁₉H₃₆O₂Si

C₁₉H₃₄O₂Si

Downstream raw materials:

(2E,4E,6E,8E,10E,12E)-13-(4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-2,7,11-trimethyltrideca-2,4,6,8,10,12-hexaenal

ethyl (2E,4E,6E,8E,10E,12E,14E)-15-(4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-4,9,13-trimethylpentadeca-2,4,6,8,10,12,14-heptaenoate

(2E,4E,6E,8E,10E,12E,14E)-15-(4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-4,9,13-trimethylpentadeca-2,4,6,8,10,12,14-heptaenal

(rac)-(E)-4-(4-hydroxy-2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-one