(S)-Lavandulol

Base Information

• Chemical Name: (S)-Lavandulol
• CAS No.: 50373-53-0
• Molecular Formula: C10H18O
• Molecular Weight: 154.252
• UNII: 8PLA23B8JZ
• DSSTox Substance ID: DTXSID50275701
• Nikkaji Number: J61.799G
• Wikidata: Q27122018
• Metabolomics Workbench ID: 28017
• Mol file: 50373-53-0.mol

Synonyms:(S)-2-Isopropenyl-5-methyl-hex-4-en-1-ol;(+)-(S)-lavandulol;(2S)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-ol;(S)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-ol;(S)-(+)-lavandulol;(+)-lavandulol;(S)-lavandulol;

Chemical Property of (S)-Lavandulol

Chemical Property:

• PSA: 20.23000
• LogP: 2.52730
• XLogP3: 3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 154.135765193
• Heavy Atom Count: 11
• Complexity: 152

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCC(CO)C(=C)C)C
• Isomeric SMILES: CC(=CC[C@H](CO)C(=C)C)C

Technology Process of (S)-Lavandulol

There total 40 articles about (S)-Lavandulol 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: 92.0%

(3S)-3-[(1-ethoxyethoxy)methyl]-2,6-dimethylhepta-1,5-diene (1298063-90-7) → (2S)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-ol (50373-53-0,21090-68-6)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; at 20 ℃; for 3h; Inert atmosphere;

DOI:10.1021/ol200779y

Reference yield: 71.0%

(2S)-Benzoesaeure(2-isopropenyl-5-methyl-4-hexenyl)ester (81757-17-7) → (2S)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-ol (50373-53-0,21090-68-6)

Guidance literature:

With potassium hydroxide; In methanol; for 5h; Ambient temperature;

DOI:10.1002/hlca.19820650132

Reference yield: 63.0%

(S)-4-benzyl-3-((S)-5-methyl-2-(prop-1-en-2-yl)hex-4-enoyl)-oxazolidin-2-one (1570098-81-5) → (2S)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-ol (50373-53-0,21090-68-6)

Guidance literature:

With lithium borohydride; In methanol; diethyl ether; at 0 - 20 ℃; for 1h; Inert atmosphere;

DOI:10.1021/jo500027k

upstream raw materials:

isopropyltriphenylphosphonium iodide

(2RS,4S)-2-hydroxy-4-isopropenyltetrahydrofuran

(4R,5S)-1,5-dimethyl-4-phenyl-3-<2'-(1-propen-2-yl)-5'-methyl-4'-hexenoyl>imidazolidin-2-one

(4S,5R)-1,5-dimethyl-4-phenyl-3-<2'-(1-propen-2-yl)-5'-methyl-4'-hexenoyl>imidazolidin-2-one

Downstream raw materials:

C₃₃H₄₂O₄

Refernces

• 1、 Pepper, Henry P.,Tulip, Stephen J.,Nakano, Yuji,George, Jonathan H.. "Biomimetic total synthesis of (±)-doitunggarcinone A and (+)-garcibracteatone". . p. 2564 - 2573. Retrieved 2014/04/17.
• 2、 Kim, Hee Jin,Su, Liang,Jung, Heejung,Koo, Sangho. "Selective deoxygenation of allylic alcohol: Stereocontrolled synthesis of lavandulol". . p. 2682 - 2685. Retrieved 2011/06/26.