8-Dodecenol

Base Information

• Chemical Name: 8-Dodecenol
• CAS No.: 42513-42-8
• Molecular Formula: C12H24O
• Molecular Weight: 184.322
• DSSTox Substance ID: DTXSID401015886
• Nikkaji Number: J610.278F
• Wikidata: Q67879656
• Metabolomics Workbench ID: 3238
• Mol file: 42513-42-8.mol

Synonyms:8-Dodecenol;42513-42-8;8-Dodecen-1-ol;8E-Dodecen-1-ol;(E)-dodec-8-en-1-ol;(E)-8-dodecenol;(e)-8-dodecen-1-ol;(8E)-8-Dodecen-1-ol #;8-dodecenol, E;(E)8-Dodecen-1-ol;(8E)-dodec-8-en-1-ol;SCHEMBL811997;SCHEMBL831510;YEQONIQGGSENJQ-SNAWJCMRSA-N;DTXSID401015886;LMFA05000148;AKOS006272403;Q67879656

Chemical Property of 8-Dodecenol

Chemical Property:

• PSA: 46.53000
• LogP: 2.66100
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 9
• Exact Mass: 184.182715385
• Heavy Atom Count: 13
• Complexity: 108

Purity/Quality:

99%,98%, ^*data from raw suppliers

(8E)-Dodecen-1-ol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCC=CCCCCCCCO
• Isomeric SMILES: CCC/C=C/CCCCCCCO
• Uses: (8E)-Dodecen-1-ol is used in the study of the photochemical transformations of biologically active mono- and diene derivatives of pheromones.

Technology Process of 8-Dodecenol

There total 7 articles about 8-Dodecenol 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:

1-penten (109-67-1) + non-8-en-1-ol (13038-21-6) → (Z)-8-dodecenol (40642-40-8) + E8,E10-dodecadien-1-ol (42513-42-8)

Guidance literature:

With C₃₂H₄₃N₃O₄Ru; In tetrahydrofuran; for 4h; Overall yield = 73 %; Overall yield = 0.56 g; diastereoselective reaction;

Reference yield:

8-hydroxyoctyltriphenylphosphine → (Z)-8-dodecenol (40642-40-8) + E8,E10-dodecadien-1-ol (42513-42-8)

Guidance literature:

8-hydroxyoctyltriphenylphosphine; With hydrogen; sodium hydride; In tetrahydrofuran; dimethyl sulfoxide; mineral oil; at 20 ℃; for 0.5h;

With butyraldehyde; In tetrahydrofuran; dimethyl sulfoxide; mineral oil; at 0 - 20 ℃; for 1.5h; Reagent/catalyst; Temperature; Overall yield = 85 %; Overall yield = 200 g;

Reference yield:

1,8-Octanediol (629-41-4) → (Z)-8-dodecenol (40642-40-8) + E8,E10-dodecadien-1-ol (42513-42-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: hydrogen bromide / toluene / 50 h / 110 °C

2.1: acetonitrile / 48 h / 94 °C

3.1: sodium hydride; hydrogen / dimethyl sulfoxide; mineral oil; tetrahydrofuran / 0.5 h / 20 °C

3.2: 1.5 h / 0 - 20 °C

With hydrogen bromide; hydrogen; sodium hydride; In tetrahydrofuran; dimethyl sulfoxide; toluene; acetonitrile; mineral oil;

upstream raw materials:

8-tetrahydropyranyloxyoctanal

n-butyl(triphenyl)phosphonium bromide

8-hydroxy-octyl-triphenyl-phosphonium bromide

butyraldehyde

Downstream raw materials:

(E)-8-dodecenyl acetate

7-Vinyldecyl acetate

Refernces

• 1、 -. "SYNTHESIS OF Z-OLEFIN-CONTAINING LEPIDOPTERAN INSECT PHEROMONES". Paragraph 0193; 0194. . Retrieved 2013/09/12.
• 2、 Vinczer, Peter,Juvanecz, Zoltan,Novak, Lajos,Szantay, Csaba. "SYNTHESIS OF PHEROMONES, III IMPROVED AND STEREOCONTROLLED SYNTHESES OF ISOMERIC MIXTURES OF 8-DODECEN-1-YL ACETATES". . p. 737 - 748. Retrieved 2007/10/02.