1-((3,5-Dichloro)-2,6-dihydroxy-4-methoxyphenyl)-1-hexanone

Base Information

• Chemical Name: 1-((3,5-Dichloro)-2,6-dihydroxy-4-methoxyphenyl)-1-hexanone
• CAS No.: 111050-72-7
• Molecular Formula: C13H16Cl2O4
• Molecular Weight: 307.174
• DSSTox Substance ID: DTXSID10149474
• Nikkaji Number: J632.607B
• Wikidata: Q27133348
• Metabolomics Workbench ID: 63438
• ChEMBL ID: CHEMBL2409648
• Mol file: 111050-72-7.mol

Synonyms:1-((3,5-dichloro)-2,6-dihydroxy-4-methoxyphenyl)-1-hexanone;1-DIF (Dictyostelium);DIF factor;DIF-1 (Dictyostelium);differentiation inducing factor;morphogen differentiation inducing factor (Dictyostelium)

Chemical Property of 1-((3,5-Dichloro)-2,6-dihydroxy-4-methoxyphenyl)-1-hexanone

Chemical Property:

• Vapor Pressure: 3.77E-08mmHg at 25°C
• Boiling Point: 434.3°Cat760mmHg
• Flash Point: 216.5°C
• PSA: 66.76000
• Density: 1.325g/cm³
• LogP: 4.17620
• Storage Temp.: 2-8°C
• Solubility.: DMSO: soluble20mg/mL, clear
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 306.0425644
• Heavy Atom Count: 19
• Complexity: 284

Purity/Quality:

99% ^*data from raw suppliers

DIF-1 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC(=O)C1=C(C(=C(C(=C1O)Cl)OC)Cl)O
• Uses: DIF-1 is a cell growth suppressor that promotes differentiation in HL-60 cells.

Technology Process of 1-((3,5-Dichloro)-2,6-dihydroxy-4-methoxyphenyl)-1-hexanone

There total 3 articles about 1-((3,5-Dichloro)-2,6-dihydroxy-4-methoxyphenyl)-1-hexanone 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: 100.0%

1-(2,6-dihydroxy-4-methoxyphenyl)hexan-1-one (142234-79-5) → 1-(3,5-dichloro-2,6-dihydroxy-4-methoxyphenyl)hexane-1-one (111050-72-7)

Guidance literature:

With sulfuryl dichloride; In methanol; dichloromethane; at 20 ℃;

Reference yield:

5-methoxyresorcinol (2174-64-3) → 1-(3,5-dichloro-2,6-dihydroxy-4-methoxyphenyl)hexane-1-one (111050-72-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 58 percent / AlCl₃ / CH₂Cl₂ / 3 h / 20 °C

2: 93 percent / SO₂Cl₂ / ethanol; CHCl₃ / 1 h / 20 °C

With aluminium trichloride; sulfuryl dichloride; In ethanol; dichloromethane; chloroform;

DOI:10.1016/j.bcp.2005.06.002

Reference yield:

Hexanoyl chloride (142-61-0) → 1-(3,5-dichloro-2,6-dihydroxy-4-methoxyphenyl)hexane-1-one (111050-72-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 58 percent / AlCl₃ / CH₂Cl₂ / 3 h / 20 °C

2: 93 percent / SO₂Cl₂ / ethanol; CHCl₃ / 1 h / 20 °C

With aluminium trichloride; sulfuryl dichloride; In ethanol; dichloromethane; chloroform;

DOI:10.1016/j.bcp.2005.06.002

upstream raw materials:

1-(2,6-dihydroxy-4-methoxyphenyl)hexan-1-one

5-methoxyresorcinol

Hexanoyl chloride

Downstream raw materials:

(3,5-dichloro-2,4,6-trihydroxyphenyl)-1-hexan-1-one

Refernces

• 1、 Gokan, Naomi,Kikuchi, Haruhisa,Nakamura, Koji,Oshima, Yoshiteru,Hosaka, Kohei,Kubohara, Yuzuru. "Structural requirements of Dictyostelium differentiation-inducing factors for their stalk-cell-inducing activity in Dictyostelium cells and anti-proliferative activity in K562 human leukemic cells". . p. 676 - 685. Retrieved 2007/10/03.
• 2、 -. "Modulators of cysteine protease". Page/Page column 19. . Retrieved 2008/06/13.