3-{(2E)-2-[(2E)-4-(methoxymethyloxy)-2-butenylidene]cyclohexyl}propanal

Base Information

• Chemical Name: 3-{(2E)-2-[(2E)-4-(methoxymethyloxy)-2-butenylidene]cyclohexyl}propanal
• CAS No.: 273936-70-2
• Molecular Formula: C₁₅H₂₄O₃
• Molecular Weight: 252.354
• Mol file: 273936-70-2.mol

Synonyms:3-{(2E)-2-[(2E)-4-(methoxymethyloxy)-2-butenylidene]cyclohexyl}propanal

Chemical Property of 3-{(2E)-2-[(2E)-4-(methoxymethyloxy)-2-butenylidene]cyclohexyl}propanal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-{(2E)-2-[(2E)-4-(methoxymethyloxy)-2-butenylidene]cyclohexyl}propanal

There total 1 articles about 3-{(2E)-2-[(2E)-4-(methoxymethyloxy)-2-butenylidene]cyclohexyl}propanal 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:

2-(3-{2-[(2E)-4-(methoxymethyloxy)-2-butenylidene]cyclohexyl}propoxy)tetrahydro-2H-pyran → 3-{(2E)-2-[(2E)-4-(methoxymethyloxy)-2-butenylidene]cyclohexyl}propanal (273936-70-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / TsOH; MeOH / 3 h / 20 °C

2: 80 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

With methanol; oxalyl dichloride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In dichloromethane; 1: Hydrolysis / 2: Swern oxidation;

DOI:10.1021/ja9939284

Reference yield:

3-{(2E)-2-[(2E)-4-(methoxymethyloxy)-2-butenylidene]cyclohexyl}propanal (273936-70-2) → benzyl (2R*,5R*,6R*)-6-[(3R*)-3-hydroxynonyl]-2-[(methoxymethoxy)methyl]-1-azaspiro[4,5]decane-1-carboxylate

Guidance literature:

Multi-step reaction with 12 steps

1.1: 83 percent / NaClO₂; 2-methyl-2-butene; NaH₂PO₄ / 2-methyl-propan-2-ol; H₂O / 2 h / 20 °C

2.1: 88 percent / diethyl ether / 0.5 h / 0 °C

3.1: 92 percent / NH₂OH*HCl; KOH / methanol / 2 h / 0 °C

4.1: 69 percent / aq. tetrabutylammonium periodate / methanol / 0.33 h / 0 °C

5.1: 95 percent / H₂ / Pd/C / methanol / 2 h / 760.05 Torr

6.1: 90 percent / Na/Hg; Na₂HPO₄; EtOH / 3 h / 0 °C

7.1: 89 percent / Et₃N; DMAP / CH₂Cl₂ / 3 h / 0 °C

8.1: 91 percent / t-BuOK / tetrahydrofuran / 0.5 h / 20 °C

9.1: LiNH₂BH₃ / tetrahydrofuran; hexane / 4 h / 20 °C

10.1: 82.5 mg / aq. Na₂CO₃ / benzene / 12 h / 20 °C

11.1: 81 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

12.1: Mg / diethyl ether

12.2: 56 percent / diethyl ether / 4 h / 0 °C

With dmap; potassium hydroxide; sodium chlorite; disodium hydrogenphosphate; sodium dihydrogenphosphate; sodium amalgam; 2-methyl-but-2-ene; oxalyl dichloride; ethanol; lithium amidotrihydroborate; hydroxylamine hydrochloride; potassium tert-butylate; hydrogen; sodium carbonate; tetrabutylammonium periodite; magnesium; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; tert-butyl alcohol; benzene; 1.1: Oxidation / 2.1: Esterification / 3.1: amidation / 4.1: oxidative Diels-Alder cycloaddition / 5.1: Catalytic hydrogenation / 6.1: Ring cleavage / 7.1: mesylation / 8.1: Cyclization / 9.1: reductive ring-opening / 10.1: Acylation / 11.1: Swern oxidation / 12.1: Grignard reaction / 12.2: Grignard reaction;

DOI:10.1021/ja9939284

Reference yield:

3-{(2E)-2-[(2E)-4-(methoxymethyloxy)-2-butenylidene]cyclohexyl}propanal (273936-70-2) → (3R*,6R*,8aS*,12aS*)-3-(tert-butyldiphenylsilyl)oxy-6-hexyldodecahydropyrido[2,1-j]quinoline

Guidance literature:

Multi-step reaction with 18 steps

1.1: 83 percent / NaClO₂; 2-methyl-2-butene; NaH₂PO₄ / 2-methyl-propan-2-ol; H₂O / 2 h / 20 °C

2.1: 88 percent / diethyl ether / 0.5 h / 0 °C

3.1: 92 percent / NH₂OH*HCl; KOH / methanol / 2 h / 0 °C

4.1: 69 percent / aq. tetrabutylammonium periodate / methanol / 0.33 h / 0 °C

5.1: 95 percent / H₂ / Pd/C / methanol / 2 h / 760.05 Torr

6.1: 92 percent / aq. HCl / methanol / 0.5 h / Heating

7.1: 95 percent / NaH; Bu₄NI / dimethylformamide / 16 h / 20 °C

8.1: 96 percent / Na/Hg; Na₂HPO₄; EtOH / 6 h / 0 °C

9.1: 92 percent / imidazole / dimethylformamide / 16 h / 20 °C

10.1: 95 percent / H₂ / Pd/C / methanol / 4 h

11.1: 86 percent / Et₃N; DMAP / CH₂Cl₂ / 7 h / 0 °C

12.1: 99 percent / NaH / tetrahydrofuran / 1 h / Heating

13.1: LiNH₂BH₃ / tetrahydrofuran; hexane / 2 h / 20 °C

14.1: 34.0 mg / Na₂CO₃ / CHCl₃; tetrahydrofuran; H₂O / 16 h / 20 °C

15.1: 88 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

16.1: Mg / diethyl ether

16.2: diethyl ether / 3 h / 0 °C

17.1: 219 mg / PCC / CH₂Cl₂ / 2 h / 20 °C

18.1: 49 percent / H₂ / Pd/C / methanol / 5 h / 760.05 Torr

With 1H-imidazole; hydrogenchloride; dmap; potassium hydroxide; sodium chlorite; disodium hydrogenphosphate; sodium dihydrogenphosphate; sodium amalgam; 2-methyl-but-2-ene; oxalyl dichloride; ethanol; lithium amidotrihydroborate; hydroxylamine hydrochloride; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium carbonate; tetrabutylammonium periodite; magnesium; dimethyl sulfoxide; triethylamine; pyridinium chlorochromate; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; chloroform; water; N,N-dimethyl-formamide; tert-butyl alcohol; 1.1: Oxidation / 2.1: Esterification / 3.1: amidation / 4.1: oxidative Diels-Alder cycloaddition / 5.1: Catalytic hydrogenation / 6.1: Hydrolysis / 7.1: Etherification / 8.1: Ring cleavage / 9.1: silylation / 10.1: Hydrogenolysis / 11.1: Tosylation / 12.1: Cyclization / 13.1: reductive ring-opening / 14.1: Acylation / 15.1: Swern oxidation / 16.1: Grignard reaction / 16.2: Grignard reaction / 17.1: Oxidation / 18.1: Hydrogenolysis;

DOI:10.1021/ja9939284

Downstream raw materials:

methyl 3-{(2E)-2-[(2E)-4-(methoxymethyloxy)-2-butenylidene]cyclohexyl}propanoate

N-hydroxy-3-{(2E)-2-[(2E)-4-(methoxymethyloxy)-2-butenylidene]cyclohexyl}propanamide