Scoparone

Base Information

• Chemical Name: Scoparone
• CAS No.: 120-08-1
• Molecular Formula: C11H10O4
• Molecular Weight: 206.198
• Hs Code.: 29322090
• European Community (EC) Number: 204-369-0
• UNII: H5841PDT4Y
• DSSTox Substance ID: DTXSID10152640
• Nikkaji Number: J5.319H
• Wikipedia: Scoparone
• Wikidata: Q15424761
• Metabolomics Workbench ID: 44581
• ChEMBL ID: CHEMBL325864
• Mol file: 120-08-1.mol

Synonyms:6,7-dimethoxy-coumarin;6,7-dimethoxycoumarin;6,7-dimethylesculetin;scoparone

Chemical Property of Scoparone

Chemical Property:

• Vapor Pressure: 1.2E-05mmHg at 25°C
• Melting Point: 145 °C
• Refractive Index: 1.556
• Boiling Point: 369.237 °C at 760 mmHg
• Flash Point: 166.813 °C
• PSA: 48.67000
• Density: 1.249 g/cm³
• LogP: 1.81020
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 206.05790880
• Heavy Atom Count: 15
• Complexity: 274

Purity/Quality:

98% ^*data from raw suppliers

Scoparone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 23/24/25-36-22
• Safety Statements: 27/28-36/37/39-45-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=C(C=C2C(=C1)C=CC(=O)O2)OC

Technology Process of Scoparone

There total 48 articles about Scoparone 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: 96.0%

aesculetin (305-01-1) + methyl iodide (74-88-4) → Scoparone (120-08-1)

Guidance literature:

With potassium carbonate; In acetone; at 110 ℃; for 1h; Microwave irradiation;

DOI:10.1002/cmdc.201000210

Reference yield: 92.0%

3,4-dimethoxyphenyl propiolate → Scoparone (120-08-1)

Guidance literature:

With Echavarren's catalyst; In dichloromethane; at 18 ℃; for 1h;

DOI:10.1021/acs.joc.0c02011

Reference yield: 91.0%

2-hydroxy-4,5-dimethoxybenzaldehyde (14382-91-3) + ethyl (triphenylphosphoranylidene)acetate (1099-45-2) → Scoparone (120-08-1)

Guidance literature:

for 0.25h; Inert atmosphere; Reflux;

DOI:10.3390/molecules181215613

upstream raw materials:

diazomethane

aesculetin

7-hydroxy-6-methoxy-2H-1-benzopyran-2-one

2-hydroxy-4,5-dimethoxybenzaldehyde

Downstream raw materials:

E-2-Hydroxy-4,5-dimethoxycinnamic acid

Z-4,5-dimethoxy-2-prenyloxycinnamic acid

(E)-3-(2,4,5-trimethoxyphenyl)prop-2-enoic acid

7-hydroxy-6-methoxy-2H-1-benzopyran-2-one

Refernces

• 1、 Xia, Yang-Liu,Wang, Jing-Jing,Li, Shi-Yang,Liu, Yong,Gonzalez, Frank J.,Wang, Ping,Ge, Guang-Bo. "Synthesis and structure-activity relationship of coumarins as potent Mcl-1 inhibitors for cancer treatment". . . Retrieved 2021.
• 2、 Brooks, Adam D.,Mohapatra, Hemakesh,Phillips, Scott T.. "Design, Synthesis, and Characterization of Small-Molecule Reagents That Cooperatively Provide Dual Readouts for Triaging and, When Necessary, Quantifying Point-of-Need Enzyme Assays". . p. 10437 - 10445. Retrieved 2015.
• 3、 Kurosawa,Harada. "-". . p. 2386. Retrieved 1979.
• 4、 Dutta et al.. "-". . p. 1167,1169. Retrieved 1975.
• 5、 Cervi, Aymeric,Vo, Yen,Chai, Christina L. L.,Banwell, Martin G.,Lan, Ping,Willis, Anthony C.. "Gold(I)-Catalyzed Intramolecular Hydroarylation of Phenol-Derived Propiolates and Certain Related Ethers as a Route to Selectively Functionalized Coumarins and 2 H-Chromenes". . p. 178 - 198. Retrieved 2020/12/22.
• 6、 Sang, Dayong,Yue, Huaxin,Zhao, Zhengdong,Yang, Pengtao,Tian, Juan. "Anchimerically Assisted Selective Cleavage of Acid-Labile Aryl Alkyl Ethers by Aluminum Triiodide and N, N-Dimethylformamide Dimethyl Acetal". . p. 6429 - 6440. Retrieved 2020/07/14.