5,8-Dimethoxy-2-acetyl-3,4-dihydronaphthalene

Base Information

• Chemical Name: 5,8-Dimethoxy-2-acetyl-3,4-dihydronaphthalene
• CAS No.: 75251-98-8
• Molecular Formula: C₁₄H₁₆O₃
• Molecular Weight: 232.279
• DSSTox Substance ID: DTXSID60453917
• Nikkaji Number: J1.165.647A
• Wikidata: Q82275211
• Mol file: 75251-98-8.mol

Synonyms:75251-98-8;5,8-Dimethoxy-2-acetyl-3,4-dihydronaphthalene;1-(5,8-dimethoxy-3,4-dihydronaphthalen-2-yl)ethanone;2-Acetyl-3,4-dihydro-5,8-dimethoxynaphthalene;SCHEMBL5697734;DTXSID60453917;YNXGVXBSQAEVTO-UHFFFAOYSA-N;AKOS015852291;FT-0729878;1,2-Dihydro-3-acetyl-5,8-dimethoxynaphthalene;2-acetyl-5,8-dimethoxy-3,4-dihydronaphthalene;2-acetyl-5.8-dimethoxy-3,4-dihydronaphthalene;1-(5,8-dimethoxy-3,4-dihydronaphthalen-2-yl)ethan-1-one

Chemical Property of 5,8-Dimethoxy-2-acetyl-3,4-dihydronaphthalene

Chemical Property:

• Boiling Point: 411.766 °C at 760 mmHg
• Flash Point: 194.515 °C
• PSA: 35.53000
• Density: 1.123 g/cm³
• LogP: 2.62240
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 232.109944368
• Heavy Atom Count: 17
• Complexity: 321

Purity/Quality:

98%Min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1=CC2=C(C=CC(=C2CC1)OC)OC

Technology Process of 5,8-Dimethoxy-2-acetyl-3,4-dihydronaphthalene

There total 27 articles about 5,8-Dimethoxy-2-acetyl-3,4-dihydronaphthalene 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: 94.0%

5.8-diacetoxy-3-acetyl-1,2-dihydronaphthalene (88928-58-9) + dimethyl sulfate (77-78-1) → 2-acetyl-5,8-dimethoxy-3,4-dihydronaphthalene (75251-98-8)

Guidance literature:

With sodium hydroxide; In methanol; for 12h; Heating;

DOI:10.1071/CH9841721

Reference yield: 88.0%

5,8-dimethoxy-3,4-dihydro-2-naphthoic acid (68569-96-0) + methyllithium (917-54-4) → 2-acetyl-5,8-dimethoxy-3,4-dihydronaphthalene (75251-98-8)

Guidance literature:

In diethyl ether; for 3h; Ambient temperature;

DOI:10.1016/S0040-4039(00)78596-0

Reference yield: 73.0%

2-(5,8-Dimethoxy-3,4-dihydro-naphthalen-2-yl)-2-methyl-[1,3]dithiolane (82407-71-4) → 2-acetyl-5,8-dimethoxy-3,4-dihydronaphthalene (75251-98-8)

Guidance literature:

With N-chloro-succinimide; silver nitrate; In water; acetonitrile; for 0.333333h; Ambient temperature;

DOI:10.1016/S0040-4039(00)87036-7

upstream raw materials:

2-Ethynyl-2-hydroxy-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalene

5,8-dimethoxy-3,4-dihydro-2-naphthoic acid

methyllithium

N,N-diphenylacetamide

Downstream raw materials:

(+/-)-2-acetyl-6-(2-methoxycarbonylbenzoyl)-5,8-dimethoxy-1,2,3,4-tetrahydro-2ol

(+/-)-2-acetyl-6-(2-carboxybenzoyl)-5,8-dimethoxy-1,2,3,4-tetrahydro-2-naphthol

(+/-)-2-acetyl-2-hydroxy-1,2,3,4-tetrahydro-5,8-dimethoxynaphthalene

(R)-2-acetyl-2-hydroxy-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalene

Refernces

• 1、 Chavan, Subhash P.,Subbarao, Y. Tripura,Gopal, Chittiboyina Amar. "Simple synthesis of 2-acetyl-5,8-dimethoxy-3,4-dihydronaphthalene: A key intermediate for the synthesis of 4-demethoxydaunomycinone". . p. 380 - 381. Retrieved 1999.
• 2、 Suzuki,Kimura,Terashima. "A novel and highly efficient asymmetric synthesis of optically active anthracyclinones". . p. 3559 - 3572. Retrieved 2007/10/02.