Pseudotsugonal

Base Information

• Chemical Name: Pseudotsugonal
• CAS No.: 42719-55-1
• Molecular Formula: C₁₅H₂₄O₂
• Molecular Weight: 236.354
• Mol file: 42719-55-1.mol

Synonyms:

Chemical Property of Pseudotsugonal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Pseudotsugonal

There total 13 articles about Pseudotsugonal 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: 94.0%

C15H26O2 (935476-11-2) → (4R)-4-((1R)-1,5-dimethyl-3-oxohexyl)cyclohex-1-enecarbaldehyde (42719-55-1)

Guidance literature:

With [bis(acetoxy)iodo]benzene; 1-methyl-2-azaadamantane-N-oxyl; In dichloromethane; at 20 ℃; for 7.5h;

DOI:10.1039/b616641e

Reference yield:

(1R,5R,8S)-8-methoxymethoxybicyclo[3.3.1]non-3-en-2-one (866398-00-7) → (4R)-4-((1R)-1,5-dimethyl-3-oxohexyl)cyclohex-1-enecarbaldehyde (42719-55-1)

Guidance literature:

Multi-step reaction with 11 steps

1: 98 percent / CuI / diethyl ether; tetrahydrofuran / 1.5 h / -40 °C

2: 83 percent / LiBF₄; H₂O / dioxane / 7 h / 50 - 70 °C

3: 91 percent / imidazole / dimethylformamide / 12 h / 20 °C

4: 66 percent / methanol / 1.5 h / 20 °C / Irradiation

5: 81 percent / CeCl₃ / tetrahydrofuran; diethyl ether / 2 h / 0 °C

6: i-Pr₂EtN; TBAI / tetrahydrofuran / 47 h / 20 °C

7: 416 mg / TBAF / tetrahydrofuran / 20 °C

8: 98 percent / Mn₂O / CH₂Cl₂ / 12 h / 20 °C

9: n-BuLi / tetrahydrofuran; hexane / 2 h / -30 °C

10: aq. HCl / tetrahydrofuran / 48 h / 20 °C

11: 94 percent / BAIB / 1-methyl-2-azaadamantane N-oxyl / CH₂Cl₂ / 7.5 h / 20 °C

With 1H-imidazole; hydrogenchloride; copper(l) iodide; lithium tetrafluoroborate; n-butyllithium; cerium(III) chloride; [bis(acetoxy)iodo]benzene; tetrabutyl ammonium fluoride; water; tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine; 1-methyl-2-azaadamantane-N-oxyl; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; 4: Norrish I reaction / 9: Wittig reaction;

DOI:10.1039/b616641e

Reference yield:

(4S)-4-((1R)-3-benzyloxymethoxy-1,5-dimethylhexyl)cyclohex-2-enone (935476-10-1) → (4R)-4-((1R)-1,5-dimethyl-3-oxohexyl)cyclohex-1-enecarbaldehyde (42719-55-1)

Guidance literature:

Multi-step reaction with 3 steps

1: n-BuLi / tetrahydrofuran; hexane / 2 h / -30 °C

2: aq. HCl / tetrahydrofuran / 48 h / 20 °C

3: 94 percent / BAIB / 1-methyl-2-azaadamantane N-oxyl / CH₂Cl₂ / 7.5 h / 20 °C

With hydrogenchloride; n-butyllithium; [bis(acetoxy)iodo]benzene; 1-methyl-2-azaadamantane-N-oxyl; In tetrahydrofuran; hexane; dichloromethane; 1: Wittig reaction;

DOI:10.1039/b616641e

upstream raw materials:

C₁₅H₂₆O₂

(1R,5R,8S)-8-methoxymethoxybicyclo[3.3.1]non-3-en-2-one

(1S,4S)-4-((1R)-3-benzyloxymethoxy-1,5-dimethylhexyl)cyclohex-2-enol

(4S)-4-((1R)-3-benzyloxymethoxy-1,5-dimethylhexyl)cyclohex-2-enone

Downstream raw materials:

(+)-(4R)-[(S)-1,5-dimethyl-3-oxohexyl]cyclohex-1-enecarboxylic acid methyl ester

Juvabion