(4R)-3,4,4aα,7,8,8aα-Hexahydro-6-methyl-4-isopropyl-1-naphthalenecarbaldehyde

Base Information

• Chemical Name: (4R)-3,4,4aα,7,8,8aα-Hexahydro-6-methyl-4-isopropyl-1-naphthalenecarbaldehyde
• CAS No.: 69394-04-3
• Molecular Formula: C15H22O
• Molecular Weight: 218.33458
• Mol file: 69394-04-3.mol

Synonyms:(-)-sclerosporal;(4R,4aS,8aR)-4-Isopropyl-6-methyl-3,4,4a,7,8,8a-hexahydro-naphthalene-1-carbaldehyde;

Chemical Property of (4R)-3,4,4aα,7,8,8aα-Hexahydro-6-methyl-4-isopropyl-1-naphthalenecarbaldehyde

Chemical Property:

• PSA: 17.07000
• LogP: 3.76010

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (4R)-3,4,4aα,7,8,8aα-Hexahydro-6-methyl-4-isopropyl-1-naphthalenecarbaldehyde

There total 35 articles about (4R)-3,4,4aα,7,8,8aα-Hexahydro-6-methyl-4-isopropyl-1-naphthalenecarbaldehyde 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: 51.0%

(4R,4aS,8aR)-6-methyl-4-(1-methylethyl)-3,4,4a,7,8,8a-hexahydronaphthalene-1-methanol (105661-29-8) → (4R, 9R, 10R)-(-)-sclerosporal (69394-04-3)

Guidance literature:

With chromic acid; In diethyl ether; at 0 ℃; for 0.166667h;

DOI:10.1016/S0040-4020(01)91347-X

Reference yield:

(1S,4R,4aS,8aR)-4-Isopropyl-6-methyl-1-phenylsulfanyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalene-1-carbaldehyde (87141-42-2) → sclerosporal (69394-04-3,97286-74-3,105595-13-9)

Guidance literature:

With sodium periodate; In 1,4-dioxane; methanol; water; at 60 ℃;

DOI:10.1016/S0040-4039(00)81749-9

Reference yield:

(R)-Carvone (6485-40-1,2244-16-8) → (+)-sclerosporal (69394-04-3,97286-74-3,105595-13-9)

Guidance literature:

Multi-step reaction with 15 steps

1: H₂ / PtO₂ / aq. ethanol / 20 °C

3: 98.8 percent / LiAlH₄ / diethyl ether / 1 h / 5 - 10 °C

4: 71.9 percent / NaOAc, PCC / CH₂Cl₂ / 2 h / Ambient temperature

5: Mg, I₂ / tetrahydrofuran / Ambient temperature

6: Et₃N / CH₂Cl₂ / 0.08 h / -10 °C

7: 54.3 percent / i-Pr₂NEt / hexamethylphosphoric acid triamide / 0.17 h / 140 °C

8: 64.9 percent / BHT / 8.5 h / 120 °C

9: LiAlH₄ / diethyl ether / 1 h / Ambient temperature

10: pyridine / 0 - 5 °C

11: 1.88 g / dimethylsulfoxide / 24 h / 60 - 70 °C

12: 0.683 g / 1.DIBAL 2.tartaric acid / hexane / 0.67 h / 0 - 45 °C

13: 0.875 g / ZnCl₂, Et₃N / benzene / 50 - 60 °C

14: 0.700 g / Ti(Oi-Pr)4, TiCl₄ / CH₂Cl₂ / 0.83 h / -78 °C

15: 0.174 g / pTsOH / xylene / 1.25 h / Heating

With titanium(IV) isopropylate; lithium aluminium tetrahydride; 2,6-di-tert-butyl-4-methyl-phenol; hydrogen; iodine; sodium acetate; titanium tetrachloride; diisobutylaluminium hydride; toluene-4-sulfonic acid; magnesium; tartaric acid; triethylamine; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; zinc(II) chloride; platinum(IV) oxide; In tetrahydrofuran; pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; ethanol; hexane; dichloromethane; dimethyl sulfoxide; xylene; benzene;

DOI:10.1016/S0040-4020(01)91347-X

upstream raw materials:

(1S,4R,4aS,8aR)-4-Isopropyl-6-methyl-1-phenylsulfanyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalene-1-carbaldehyde

6-isopropyl-9-methyl-deca-1,7t,9-trien-3-ol

(4S,4aR,8aS)-4-Isopropyl-1-(methoxy-phenylsulfanyl-methyl)-6-methyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-ol

6-methyl-4-(1'-methylethyl)-3,4,4a,7,8,8a-hexahydro-1(2H)-naphthalenone

Downstream raw materials:

sclerosporin

(4R, 9R, 10R)-(+)-sclerosporin

(4R,4aS,8aS)-4-Isopropyl-6-methyl-3,4,4a,7,8,8a-hexahydro-naphthalene-1-carboxylic acid

(-)-sclerosporin

Refernces

Synthesis of the enantiomers of sclerosporin and sclerosporal to determine the absolute configuration of the natural products

10.1016/S0040-4039(01)91234-1

The study focused on the synthesis of sclerostin and enantiomers of sclerostin to determine their absolute configurations. The researchers synthesized both enantiomers from (-)-carvone using intermolecular and intramolecular Diels-Alder reactions. The key chemicals involved included (-)-carvone as a starting material, PCC-NaOAc for oxidation to form the aldehyde, methylallylmagnesium bromide for allylation, and methacrylate for the Diels-Alder reaction. The study identified (4R, 9R, 10R)-(+)-sclerostin and (4R, 9R, 10R)-(-)-sclerostin as natural enantiomers by bioassay and CD spectral comparison. The spectral data of the synthesized sclerostin and sclerostin were exactly the same as those of the authentic samples, and the study found that (+)-sclerostin had strong sporulation activity, while (-)-sclerostin only showed weak activity.

SYNTHESIS OF COMPOUNDS RELATED TO SCLEROSPORAL

10.1246/cl.1982.1715

The research aimed at synthesizing compounds related to sclerosporal, a metabolite of Sclerotinia flucticola, to confirm its proposed guaianoid structure. The researchers synthesized two optically active aldehydes, 3 and 4, which were thought to possess the planar structure for sclerosporal. Starting from (-)-carvone, various chemicals were used in the process, including 1,3-dibromo-2-pentene for alkylation, Hg(OAc)2 and HCO2H for treatment to yield diones and formates, DDQ for dehydrogenation, and Li-NH3 for reduction. The study concluded that the proposed structures for sclerosporal and sclerosporin were erroneous, as the synthetic aldehydes 3 and 4 did not match the spectral data of natural sclerosporal, necessitating a revision of the structures. The research also highlighted the importance of further studies to confirm the suggested mechanisms of the reactions involved.