(2S,3S,4S)-2-methoxy-3-[(2E)-6-methylhept-2-en-2-yl]-4-(trifluoroacetyl)cyclohexanone

Base Information

• Chemical Name: (2S,3S,4S)-2-methoxy-3-[(2E)-6-methylhept-2-en-2-yl]-4-(trifluoroacetyl)cyclohexanone
• CAS No.: 849676-39-7
• Molecular Formula: C17H25F3O3
• Molecular Weight: 334.379
• DSSTox Substance ID: DTXSID301117938
• Wikidata: Q27121193
• Metabolomics Workbench ID: 56976
• Mol file: 849676-39-7.mol

Synonyms:(2S,3S,4S)-2-methoxy-3-[(2E)-6-methylhept-2-en-2-yl]-4-(trifluoroacetyl)cyclohexanone;2(S)-3(S)-4(S)-3-(1,5-dimethyl-hex-1-enyl)-2-methoxy-4-(2,2,2-trifluoroacetyl)-cyclohexanone;SCHEMBL8268518;CHEBI:48412;MUKXQNBCKOXHTO-HRYNPVEISA-N;DTXSID301117938;Q27121193;(2S,3S,4S)-2-methoxy-3-[(E)-6-methylhept-2-en-2-yl]-4-(2,2,2-trifluoroacetyl)cyclohexan-1-one;(2S,3S,4S)-3-[(1E)-1,5-Dimethyl-1-hexen-1-yl]-2-methoxy-4-(2,2,2-trifluoroacetyl)cyclohexanone;849676-39-7

Chemical Property of (2S,3S,4S)-2-methoxy-3-[(2E)-6-methylhept-2-en-2-yl]-4-(trifluoroacetyl)cyclohexanone

Chemical Property:

• XLogP3: 4.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 334.17557914
• Heavy Atom Count: 23
• Complexity: 466

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)CCC=C(C)C1C(CCC(=O)C1OC)C(=O)C(F)(F)F
• Isomeric SMILES: CC(C)CC/C=C(\C)/[C@@H]1[C@H](CCC(=O)[C@H]1OC)C(=O)C(F)(F)F

Technology Process of (2S,3S,4S)-2-methoxy-3-[(2E)-6-methylhept-2-en-2-yl]-4-(trifluoroacetyl)cyclohexanone

There total 13 articles about (2S,3S,4S)-2-methoxy-3-[(2E)-6-methylhept-2-en-2-yl]-4-(trifluoroacetyl)cyclohexanone 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: 40.0%

(trifluoromethyl)trimethylsilane (81290-20-2) + 1(S)-2(S)-3(S)-2-(1,5-dimethyl-hex-1-enyl)-3-methoxy-4-oxo-cyclohexanecarbaldehyde (849676-38-6) → 2(S)-3(S)-4(S)-3-(1,5-dimethyl-hex-1-enyl)-2-methoxy-4-(2,2,2-trifluoro-acetyl)-cyclohexanone (849676-39-7)

Guidance literature:

(trifluoromethyl)trimethylsilane; 1(S)-2(S)-3(S)-2-(1,5-dimethyl-hex-1-enyl)-3-methoxy-4-oxo-cyclohexanecarbaldehyde; With tetrabutyl ammonium fluoride; In tetrahydrofuran;

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 0.5h;

With Dess-Martin periodane; In dichloromethane; at 0 ℃;

Reference yield:

(2S,3S,4S)-3-((E)-1,5-Dimethyl-hex-1-enyl)-2-methoxy-4-(2,2,2-trifluoro-1-hydroxy-ethyl)-cyclohexanone → 2(S)-3(S)-4(S)-3-(1,5-dimethyl-hex-1-enyl)-2-methoxy-4-(2,2,2-trifluoro-acetyl)-cyclohexanone (849676-39-7)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 0 ℃; for 16h;

DOI:10.1021/jo047858h

Reference yield:

4-hydroxymethyl-cyclohexanone (38580-68-6) → 2(S)-3(S)-4(S)-3-(1,5-dimethyl-hex-1-enyl)-2-methoxy-4-(2,2,2-trifluoro-acetyl)-cyclohexanone (849676-39-7)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 75 percent / imidazole / dimethylformamide; tetrahydrofuran / 2 h / 20 °C

2.1: (+)-bis(α-methylbenzylamine) hydrochloride; BuLi / tetrahydrofuran / 2 h / -100 - -95 °C

3.1: 1.37 g / O₂ / Pd(OAc)2 / dimethylsulfoxide / 16 h / 20 °C

4.1: t-BuLi; lithium 2-thienylcyanocuprate / pentane; tetrahydrofuran / 0.5 h / -78 °C

4.2: pentane; tetrahydrofuran / 0.5 h

5.1: KHCO₃; mCPBA / CH₂Cl₂ / 1 h / 0 °C

5.2: 1.04 g / TFA / methanol; tetrahydrofuran

6.1: 96 percent / Ag₂O / diethyl ether / 3 h / 40 °C

7.1: 84 percent / TBAF / tetrahydrofuran / 4 h / 20 °C

8.1: 83 percent / Dess-Martin periodinate / CH₂Cl₂; H₂O / 2 h / 20 °C

9.1: TBAF / tetrahydrofuran / 1 h / 0 °C

9.2: TBAF / tetrahydrofuran / 0.5 h

10.1: 25 mg / Dess-Martin periodinate / CH₂Cl₂ / 16 h / 0 °C

With 1H-imidazole; n-butyllithium; tetrabutyl ammonium fluoride; (R,R)-(+)-bis[alpha-methylbenzyl]amine hydrochloride; tert.-butyl lithium; oxygen; potassium hydrogencarbonate; Dess-Martin periodane; thien-2-yl(cyano)copper lithium; 3-chloro-benzenecarboperoxoic acid; silver(l) oxide; palladium diacetate; In tetrahydrofuran; diethyl ether; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; pentane; 8.1: Dess-Martin oxidation / 10.1: Dess-Martin oxidation;

DOI:10.1021/jo047858h

upstream raw materials:

isopentyl iodide

4-hydroxymethyl-cyclohexanone

(E)-2-bromo-6-methylhept-2-ene

4(S)-4-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohex-2-enone