(3R)-3-Methoxydecan-1-OL

Base Information

• Chemical Name: (3R)-3-Methoxydecan-1-OL
• CAS No.: 185954-75-0
• Molecular Formula: C11H24O2
• Molecular Weight: 188.31
• DSSTox Substance ID: DTXSID20692941
• Wikidata: Q82621974
• Mol file: 185954-75-0.mol

Synonyms:(3R)-3-METHOXYDECAN-1-OL;185954-75-0;1-Decanol, 3-methoxy-, (3R)-;SCHEMBL12371512;DTXSID20692941

Chemical Property of (3R)-3-Methoxydecan-1-OL

Chemical Property:

• PSA: 29.46000
• LogP: 2.74430
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 9
• Exact Mass: 188.177630004
• Heavy Atom Count: 13
• Complexity: 94.1

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCC(CCO)OC
• Isomeric SMILES: CCCCCCC[C@H](CCO)OC

Technology Process of (3R)-3-Methoxydecan-1-OL

There total 6 articles about (3R)-3-Methoxydecan-1-OL 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:

(R)-tert-butyl(3-methoxydecyloxy)dimethylsilane → (R)-3-methoxydecan-1-ol (185954-75-0)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 10h; Inert atmosphere;

DOI:10.1007/s00044-013-0466-y

Reference yield:

(E)-2-decenol (18409-18-2) → (R)-3-methoxydecan-1-ol (185954-75-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: Ti(OPri)4; diethyl (2S,3S)-tartrate; tert.-butylhydroperoxide / 2,2,4-trimethylpentane; dichloromethane / 3 h / -40 - -20 °C / Inert atmosphere; Molecular sieve

2.1: Red-Al / toluene; tetrahydrofuran / 4 h / 0 °C / Inert atmosphere

3.1: dmap; 1H-imidazole / dichloromethane / 10 h / 0 - 20 °C / Inert atmosphere

4.1: sodium hydride / mineral oil; tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

4.2: 10 h / 20 °C / Inert atmosphere

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 10 h / 20 °C / Inert atmosphere

With 1H-imidazole; tert.-butylhydroperoxide; dmap; Red-Al; diethyl (2S,3S)-tartrate; Ti(OPri)4; tetrabutyl ammonium fluoride; sodium hydride; In tetrahydrofuran; 2,2,4-trimethylpentane; dichloromethane; toluene; mineral oil; 1.1: |Sharpless Asymmetric Epoxidation;

DOI:10.1007/s00044-013-0466-y

Reference yield:

Octanal (124-13-0) → (R)-3-methoxydecan-1-ol (185954-75-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.25 h / -78 °C / Inert atmosphere

1.2: 0.5 h / -78 °C / Inert atmosphere

1.3: 0.25 h / -78 °C / Inert atmosphere

2.1: Ti(OPri)4; diethyl (2S,3S)-tartrate; tert.-butylhydroperoxide / 2,2,4-trimethylpentane; dichloromethane / 3 h / -40 - -20 °C / Inert atmosphere; Molecular sieve

3.1: Red-Al / toluene; tetrahydrofuran / 4 h / 0 °C / Inert atmosphere

4.1: dmap; 1H-imidazole / dichloromethane / 10 h / 0 - 20 °C / Inert atmosphere

5.1: sodium hydride / mineral oil; tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

5.2: 10 h / 20 °C / Inert atmosphere

6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 10 h / 20 °C / Inert atmosphere

With 1H-imidazole; tert.-butylhydroperoxide; dmap; n-butyllithium; Red-Al; diethyl (2S,3S)-tartrate; Ti(OPri)4; tetrabutyl ammonium fluoride; sodium hydride; In tetrahydrofuran; 2,2,4-trimethylpentane; hexane; dichloromethane; toluene; mineral oil; 1.1: |Horner-Wadsworth-Emmons Olefination / 2.1: |Sharpless Asymmetric Epoxidation;

DOI:10.1007/s00044-013-0466-y

upstream raw materials:

(E)-2-decenol

Octanal

((2R,3R)-3-heptyloxiran-2-yl)methanol

(R)-decane-1,3-diol

Refernces