(S)-4-Dodecanolide

Base Information

• Chemical Name: (S)-4-Dodecanolide
• CAS No.: 69830-92-8
• Molecular Formula: C12H22O2
• Molecular Weight: 198.30188
• UNII: K3LQN723IF
• ChEMBL ID: CHEMBL1269378
• Nikkaji Number: J324.776G
• Wikidata: Q27281912
• Mol file: 69830-92-8.mol

Synonyms:(s)-gamma-dodecalactone;(S)-4-DODECANOLIDE;69830-92-8;(S)-4-N-Octylbutyrolactone;(5S)-5-octyloxolan-2-one;(S)-gamma-Dodecanolide;UNII-K3LQN723IF;gamma-Dodecalactone, (S)-;K3LQN723IF;2(3H)-Furanone, dihydro-5-octyl-, (S)-;2(3H)-Furanone, dihydro-5-octyl-, (5S)-;(S)-4-DODECANOLIDE STANDARD FOR GC;(R)-.gamma.-dodecalactone;SCHEMBL2077607;CHEMBL1269378;(S)-.GAMMA.-DODECANOLIDE;CHEBI:143727;(S)-.GAMMA.-DODECALACTONE;MFCD01863028;(S)-5-Octyldihydrofuran-2(3H)-one;.GAMMA.-DODECALACTONE, (S)-;AKOS006279063;(5S)-dihydro-5-octyl-2(3H)-furanone;Q27281912

Chemical Property of (S)-4-Dodecanolide

Chemical Property:

• PSA: 26.30000
• LogP: 3.44260
• Storage Temp.: ?20°C
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 7
• Exact Mass: 198.161979940
• Heavy Atom Count: 14
• Complexity: 166

Purity/Quality:

95% ^*data from raw suppliers

(S)-4-DODECANOLIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCC1CCC(=O)O1
• Isomeric SMILES: CCCCCCCC[C@H]1CCC(=O)O1

Technology Process of (S)-4-Dodecanolide

There total 59 articles about (S)-4-Dodecanolide 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: 99.0%

(S)-4-Hydroxy-dodecanoic acid benzylamide → 5(S)-octyl-2(3H)-dihydrofuranone (69830-92-8,2305-05-7)

Guidance literature:

(S)-4-Hydroxy-dodecanoic acid benzylamide; With methanol; sodium hydroxide; for 3h; Reflux;

With hydrogenchloride; In water; at 20 ℃; for 1h;

DOI:10.1080/00397910903134618

Reference yield: 88.0%

4-hydroxy-dodecanoic acid benzylamide (125751-43-1) → 5(S)-octyl-2(3H)-dihydrofuranone (69830-92-8,2305-05-7)

Guidance literature:

4-hydroxy-dodecanoic acid benzylamide; With vinyl acetate; Novozym 435; In diethyl ether; at 20 ℃; Enzymatic reaction;

With di-isopropyl azodicarboxylate; triphenylphosphine; 4-nitro-benzoic acid; In benzene; at 20 ℃; for 48h; optical yield given as %ee; Further stages;

DOI:10.1080/00397910802546177

Reference yield: 66.0%

(4R,5S)-5-Octyl-4-phenylsulfanyl-dihydro-furan-2-one → 5(S)-octyl-2(3H)-dihydrofuranone (69830-92-8,2305-05-7)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 90 ℃;

DOI:10.1021/jo960078r

upstream raw materials:

(±)-4-hydroxydodecanoic acid

n-heptyllithium

(R)-(-)-γ-<(tosyloxy)methyl>-γ-butyrolactone

2-(1-Bromo-octyl)-tetrahydro-furan

Refernces

• 1、 Miura, Tomoya,Oku, Naoki,Murakami, Masahiro. "Diastereo- and Enantioselective Synthesis of (E)-δ-Boryl-Substituted anti-Homoallylic Alcohols in Two Steps from Terminal Alkynes". supporting information. p. 14620 - 14624. Retrieved 2019/09/06.
• 2、 Matsumoto, Kazutsugu,Usuda, Kazumasa,Okabe, Hirokazu,Hashimoto, Manabu,Shimada, Yasutaka. "Synthesis of optically active heterocyclic compounds via deracemization of 1,2-diol monotosylate derivatives bearing a long aliphatic chain by a combination of enzymatic hydrolysis with Mitsunobu inversion". . p. 108 - 115. Retrieved 2013/04/23.