3,3-dimethyl-3H-benzo[f]chromene

Base Information

• Chemical Name: 3,3-dimethyl-3H-benzo[f]chromene
• CAS No.: 19836-62-5
• Molecular Formula: C₁₅H₁₄O
• Molecular Weight: 210.276
• NSC Number: 115097
• DSSTox Substance ID: DTXSID30297289
• Nikkaji Number: J849.571H
• Wikidata: Q82038314
• Mol file: 19836-62-5.mol

Synonyms:19836-62-5;3,3-dimethyl-3H-benzo[f]chromene;NSC115097;3,3-dimethyl naphthopyran;3,3-dimethyl-benzo[f]chromene;DTXSID30297289;NSC-115097

Chemical Property of 3,3-dimethyl-3H-benzo[f]chromene

Chemical Property:

• Vapor Pressure: 0.000189mmHg at 25°C
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 210.104465066
• Heavy Atom Count: 16
• Complexity: 292

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1(C=CC2=C(O1)C=CC3=CC=CC=C32)C

Technology Process of 3,3-dimethyl-3H-benzo[f]chromene

There total 24 articles about 3,3-dimethyl-3H-benzo[f]chromene 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: 98.0%

2-((2-methylbut-3-yn-2-yl)oxy)naphthalene (111492-39-8) → 3,3-dimethyl-3H-benzo[f]chromene (19836-62-5)

Guidance literature:

With aluminum oxide; for 0.0666667h; microwave irradiation;

DOI:10.1515/HC.2003.9.5.519

Reference yield: 95.0%

3,3-dimethyl acrylaldehyde (107-86-8) + β-naphthol (135-19-3) → 3,3-dimethyl-3H-benzo[f]chromene (19836-62-5)

Guidance literature:

With acetic acid; phenylboronic acid; In toluene; for 16h; Heating;

DOI:10.1055/s-1998-2042

Reference yield: 90.0%

1-(1-Hydroxy-3-methyl-but-2-enyl)-naphthalen-2-ol (88252-75-9) → 3,3-dimethyl-3H-benzo[f]chromene (19836-62-5)

Guidance literature:

With magnesium sulfate; In diethyl ether;

DOI:10.1055/s-1983-30540

upstream raw materials:

methyl magnesium iodide

3H-benzo[f]chromen-3-one

3, 3-dimethyl-2,3-dihydro-1H-benzo[f]chromene

1-(3-methylbut-2-enyl)naphthalen-2-ol ?

Downstream raw materials:

3,3-dimethyl-2,3-dihydro-benzo[f]chromen-1-one-(2,4-dinitro-phenylhydrazone)

3,3,-dimethyl-2-phenylsulphonyl-2,3-dihydro-1H-naphtho<2,1-b>pyran

3,3-dimethyl-2-phenylthio-2,3-dihydro-1H-naphtho<2,1-b>pyran

Refernces

• 1、 Lamcharfi,Menguy,Zamarlik. "One-pot synthesis of analogues of precocenes and isoprenyl-chromenes". . p. 3019 - 3028. Retrieved 1993.
• 2、 Zeng, Hanxiang,Ju, Jia,Hua, Ruimao. "ReCl(CO)5-catalyzed cyclocondensation of phenols with 2-methyl-3-butyn-2-ol to afford 2,2-dimethyl-2H-chromenes". . p. 3926 - 3928. Retrieved 2011.
• 3、 Yong, Rok Lee,Yun, Mi Kim. "A novel method for the synthesis of substituted benzochromenes by ethylenediamine diacetate-catalyzed cyclizations of naphthalenols to α,β-unsaturated aldehydes. Concise synthesis of the natural products lapachenole, dihydrolapachenole, and mollugin". . p. 2401 - 2413. Retrieved 2007.
• 4、 Kumar, Prashant,Kumar, Pravesh,Venkataramani, Sugumar,Ramasastry. "Pd-Catalyzed Formal [3 + 3] Heteroannulation of Allylic gem-Diacetates: Synthesis of Chromene-Based Natural Products and Exploration of Photochromic Properties". . p. 963 - 970. Retrieved 2022/01/19.
• 5、 Dimakos, Victoria,Singh, Tishaan,Taylor, Mark S.. "Boronic acid/Br?nsted acid co-catalyst systems for the synthesis of 2: H -chromenes from phenols and α,β-unsaturated carbonyls". . p. 6703 - 6711. Retrieved 2016/07/21.