Hexa-2,4-diensA currencyure

Base Information

• Chemical Name: Hexa-2,4-diensA currencyure
• CAS No.: 22500-92-1
• Molecular Formula: C₆H₈O₂
• Molecular Weight: 112.128
• DSSTox Substance ID: DTXSID20859193
• Wikidata: Q106956351
• Metabolomics Workbench ID: 75590
• ChEMBL ID: CHEMBL4303486
• Mol file: 22500-92-1.mol

Synonyms:(2E,4E)-2,4-Hexenoic acid;2,4 hexadienoic acid;Hexa-2,4-diensA currencyure;CHEMBL4303486;DTXSID20859193;LMFA01031012;AKOS030229959;FT-0645130;FT-0652289;TRANS, TRANS-2,4-HEXADIENOIC ACID, ACIDUM SORBICUM, 2e,4e-hexadienoicacid

Chemical Property of Hexa-2,4-diensA currencyure

Chemical Property:

• PSA: 37.30000
• LogP: 1.20330
• Solubility.: Slightly soluble in water, freely soluble in ethanol (96 per cent).
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 112.052429494
• Heavy Atom Count: 8
• Complexity: 123

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC=CC=CC(=O)O
• Uses: Pharmaceutic aid (antimicrobial agent).

Technology Process of Hexa-2,4-diensA currencyure

There total 17 articles about Hexa-2,4-diensA currencyure 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: 79.0%

(but-2-enylidene)malonic acid (4423-18-1) → (2Z,4E)-hexa-2,4-dienoic acid (110-44-1,5309-56-8,5309-57-9,22500-92-1,30361-30-9,91751-55-2)

Guidance literature:

With quinoline; at 130 ℃; for 3h;

DOI:10.1021/ja020635t

Reference yield: 54.0%

3-butenoic acid 1-methyl-2-propen-1-yl ester → (2Z,4E)-hexa-2,4-dienoic acid (110-44-1,5309-56-8,5309-57-9,22500-92-1,30361-30-9,91751-55-2)

Guidance literature:

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; sodium hydride; In toluene; mineral oil; at 65 ℃; for 4.5h;

DOI:10.1002/anie.202106250

Reference yield: 38.0%

(Z)-3-iodobut-2-enoic acid (34450-60-7) + (E)-propenyl-tri-n-butylstannane (105494-65-3,66680-85-1,66680-84-0) → (2Z,4E)-hexa-2,4-dienoic acid (110-44-1,5309-56-8,5309-57-9,22500-92-1,30361-30-9,91751-55-2)

Guidance literature:

dichloro bis(acetonitrile) palladium(II); In N,N-dimethyl-formamide; at 20 ℃; for 7h;

DOI:10.1021/ol025558l

upstream raw materials:

pyridine

cis-5-Hydroxyhex-2-en-1-saeureethylester

p-toluenesulfonyl chloride

hex-4t-en-2-ynoic acid

Downstream raw materials:

hexa-2c,4t-dienoic acid isobutylamide

(2Z,4E)-Hexa-2,4-dienoic acid [(S)-((2E,8E,10Z,14E)-(1R,5R,13R,17R)-13-hydroxy-3,11-dimethyl-19-methylene-7-oxo-6,21-dioxa-bicyclo[15.3.1]henicosa-2,8,10,14-tetraen-5-yl)-(4-methoxy-benzyloxy)-methyl]-amide

(2Z,4E)-Hexa-2,4-dienoic acid [(S)-((2E,8E,10Z,14E)-(1R,5R,17R)-3,11-dimethyl-19-methylene-7,13-dioxo-6,21-dioxa-bicyclo[15.3.1]henicosa-2,8,10,14-tetraen-5-yl)-(4-methoxy-benzyloxy)-methyl]-amide

(2Z,4E)-Hexa-2,4-dienoic acid [(S)-[(2E,8E,10Z,14E)-(1R,5R,13R,17R)-13-(tert-butyl-dimethyl-silanyloxy)-3,11-dimethyl-19-methylene-7-oxo-6,21-dioxa-bicyclo[15.3.1]henicosa-2,8,10,14-tetraen-5-yl]-(4-methoxy-benzyloxy)-methyl]-amide

Refernces

• 1、 Sun, Chang-Liang,Fuerstner, Alois. "Formal ring-opening/cross-coupling reactions of 2-pyrones: Iron-catalyzed entry into stereodefined dienyl carboxylates". supporting information. p. 13071 - 13075. Retrieved 2014/01/06.
• 2、 Smith III, Amos B.,Safonov, Igor G.,Corbett, R. Michael. "Total syntheses of (+)-zampanolide and (+)-dactylolide exploiting a unified strategy". . p. 11102 - 11113. Retrieved 2007/10/03.