5,6-Dihydro-1H,4H-naphtho[1,8-cd]pyran-1-one

Base Information

• Chemical Name: 5,6-Dihydro-1H,4H-naphtho[1,8-cd]pyran-1-one
• CAS No.: 14935-18-3
• Molecular Formula: C₁₂H₁₀O₂
• Molecular Weight: 186.21
• Hs Code.: 2932999099
• DSSTox Substance ID: DTXSID80461892
• Nikkaji Number: J1.375.463B
• Wikidata: Q82286347
• Mol file: 14935-18-3.mol

Synonyms:14935-18-3;5,6-Dihydro-1H,4H-naphtho[1,8-cd]pyran-1-one;5,6-Dihydrobenzo[de]isochromen-1(4H)-one;3-oxatricyclo[7.3.1.05,13]trideca-1(12),4,9(13),10-tetraen-2-one;5,6-Dihydro-1H,4H-benzo[de]isochromen-1-one;1H,4H-Naphtho[1,8-cd]pyran-1-one,5,6-dihydro-;DTXSID80461892;AKOS006325365;FT-0701638;A18220;1H,4H-Naphtho[1,8-cd]pyran-1-one,5,6-dihydro

Chemical Property of 5,6-Dihydro-1H,4H-naphtho[1,8-cd]pyran-1-one

Chemical Property:

• Boiling Point: 372.5±42.0 °C(Predicted)
• PSA: 30.21000
• Density: 1.26±0.1 g/cm3(Predicted)
• LogP: 2.28170
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 186.068079557
• Heavy Atom Count: 14
• Complexity: 293

Purity/Quality:

97% ^*data from raw suppliers

5,6-Dihydro-1h,4h-benzo[de]isochromen-1-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2=C3C(=COC(=O)C3=CC=C2)C1

Technology Process of 5,6-Dihydro-1H,4H-naphtho[1,8-cd]pyran-1-one

There total 5 articles about 5,6-Dihydro-1H,4H-naphtho[1,8-cd]pyran-1-one 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: 77.0%

N,N-Diethyl-8-formyl-5,6,7,8-tetrahydronaphthalene-1-carboxamide (296281-85-1) → 5,6-Dihydro-1H,4H-naphto[1,8-cd]pyran-1-one (14935-18-3)

Guidance literature:

With hydrogenchloride; for 0.75h;

DOI:10.1055/s-2000-6321

Reference yield:

5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid (4242-18-6) → 5,6-Dihydro-1H,4H-naphto[1,8-cd]pyran-1-one (14935-18-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: SOCl₂; DMF / toluene / 1.42 h / 20 - 50 °C

2.1: 13.14 g / toluene / 0 °C

3.1: BuLi / tetrahydrofuran; hexane / 0.67 h / -70 - -65 °C

3.2: 92 percent / tetrahydrofuran; hexane / -70 - 20 °C

4.1: 77 percent / aq. HCl / 0.75 h

With hydrogenchloride; n-butyllithium; thionyl chloride; N,N-dimethyl-formamide; In tetrahydrofuran; hexane; toluene; 1.1: Substitution / 2.1: Acylation / 3.1: Metallation / 3.2: Formylation / 4.1: Cyclization;

DOI:10.1055/s-2000-6321

Reference yield:

5,6,7,8-tetrahydronaphthylene-1-carboxylic acid chloride (110808-69-0) → 5,6-Dihydro-1H,4H-naphto[1,8-cd]pyran-1-one (14935-18-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 13.14 g / toluene / 0 °C

2.1: BuLi / tetrahydrofuran; hexane / 0.67 h / -70 - -65 °C

2.2: 92 percent / tetrahydrofuran; hexane / -70 - 20 °C

3.1: 77 percent / aq. HCl / 0.75 h

With hydrogenchloride; n-butyllithium; In tetrahydrofuran; hexane; toluene; 1.1: Acylation / 2.1: Metallation / 2.2: Formylation / 3.1: Cyclization;

DOI:10.1055/s-2000-6321

upstream raw materials:

N,N-Diethyl-8-formyl-5,6,7,8-tetrahydronaphthalene-1-carboxamide

5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid

5,6,7,8-tetrahydronaphthylene-1-carboxylic acid chloride

N,N-Diethyl-5,6,7,8-tetrahydronaphthalene-1-carboxamide

Downstream raw materials:

(S)-2-(1-azabicyclo[2.2.2]oct-3-yl)-2,4,5,6-tetrahydro-1H-benz[de]isoquinolin-1-one