6-Methoxy-1a,2,3,7b-tetrahydronaphtho[1,2-b]oxirene

Base Information

• Chemical Name: 6-Methoxy-1a,2,3,7b-tetrahydronaphtho[1,2-b]oxirene
• CAS No.: 63320-02-5
• Molecular Formula: C11H12O2
• Molecular Weight: 176.215
• DSSTox Substance ID: DTXSID90557199
• Nikkaji Number: J645.259K
• Mol file: 63320-02-5.mol

Synonyms:63320-02-5;6-methoxy-1a,2,3,7b-tetrahydronaphtho[1,2-b]oxirene;6-Methoxy-1a,2,3,7b-tetrahydro-1-oxa-cyclopropa[a]naphthalene;SCHEMBL4119570;DTXSID90557199;AKOS006291233

Chemical Property of 6-Methoxy-1a,2,3,7b-tetrahydronaphtho[1,2-b]oxirene

Chemical Property:

• PSA: 21.76000
• LogP: 2.08130
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 176.083729621
• Heavy Atom Count: 13
• Complexity: 204

Purity/Quality:

98% ^*data from raw suppliers

6-METHOXY-1A,2,3,7B-TETRAHYDRO-1-OXA-CYCLOPROPA[A]NAPHTHALENE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC2=C(CCC3C2O3)C=C1

Technology Process of 6-Methoxy-1a,2,3,7b-tetrahydronaphtho[1,2-b]oxirene

There total 4 articles about 6-Methoxy-1a,2,3,7b-tetrahydronaphtho[1,2-b]oxirene 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: 95.0%

7-methoxy-3,4-dihydronaphthalene (60573-58-2) → 6-methoxy-1a,2,3,7b-tetrahydronaphtho[1,2-b]oxirene (63320-02-5)

Guidance literature:

With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In toluene; for 2h; Ambient temperature;

DOI:10.1021/jm9801859

Reference yield:

2-bromo-7-methoxy-1,2,3,4-tetrahydronaphthalen-1-ol (886040-06-8) → 6-methoxy-1a,2,3,7b-tetrahydronaphtho[1,2-b]oxirene (63320-02-5)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 20 ℃; for 4h;

Reference yield:

7-Methoxy-1-tetralone (6836-19-7) → 6-methoxy-1a,2,3,7b-tetrahydronaphtho[1,2-b]oxirene (63320-02-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 51.1 g / NaBH₄ / methanol; tetrahydrofuran / 2 h / Ambient temperature

2: pyridinium p-toluenesulfonate / toluene / 3 h / Heating

3: 95 percent / 10percent aq. NaHCO₃, 3-chloroperbenzoic acid / toluene / 2 h / Ambient temperature

With sodium tetrahydroborate; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; toluene;

DOI:10.1021/jm9801859

upstream raw materials:

7-methoxy-3,4-dihydronaphthalene

7-methoxy-1,2,3,4-tetrahydro-1-naphthol

7-Methoxy-1-tetralone

2-bromo-7-methoxy-1,2,3,4-tetrahydronaphthalen-1-ol

Downstream raw materials:

[7-(4-Cyano-benzyloxy)-1,2,3,4-tetrahydro-naphthalen-2-yl]-acetic acid ethyl ester

ethyl {7-[2-(4-cyanophenyl)ethyl]-1,2,3,4-tetrahydro-2-naphthalenyl}acetate

[7-(4-Cyano-benzyloxy)-naphthalen-2-yl]-acetic acid ethyl ester

7-methoxyl-2-tetralone

Refernces

• 1、 Hashimoto, Norio,Kanda, Atsushi. "Practical and environmentally friendly epoxidation of olefins using Oxone". . p. 405 - 406. Retrieved 2013/09/06.
• 2、 Craig, J. Cymerman,Torkelson, Steven M.,Findell, Paul R.,Weiner, Richard I.. "Synthesis and Dopaminergic Activity of 2-Substituted Octahydrobenzoquinolines". . p. 961 - 968. Retrieved 2007/10/02.