Diethylcarbamic acid 2-[2-methoxy-4-(methoxymethoxy)phenyl]-4-methoxy-5-isopropoxy-1-naphthyl ester

Base Information

• Chemical Name: Diethylcarbamic acid 2-[2-methoxy-4-(methoxymethoxy)phenyl]-4-methoxy-5-isopropoxy-1-naphthyl ester
• CAS No.: 199858-21-4
• Molecular Formula: C₂₈H₃₅NO₇
• Molecular Weight: 497.588
• DSSTox Substance ID: DTXSID501111855
• Nikkaji Number: J924.765C
• Mol file: 199858-21-4.mol

Synonyms:DTXSID501111855;199858-21-4;4-Methoxy-2-[2-methoxy-4-(methoxymethoxy)phenyl]-5-(1-methylethoxy)-1-naphthalenyl N,N-diethylcarbamate;Diethylcarbamic acid 2-[2-methoxy-4-(methoxymethoxy)phenyl]-4-methoxy-5-isopropoxy-1-naphthyl ester

Chemical Property of Diethylcarbamic acid 2-[2-methoxy-4-(methoxymethoxy)phenyl]-4-methoxy-5-isopropoxy-1-naphthyl ester

Chemical Property:

• XLogP3: 5.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 12
• Exact Mass: 497.24135246
• Heavy Atom Count: 36
• Complexity: 658

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCN(CC)C(=O)OC1=C2C=CC=C(C2=C(C=C1C3=C(C=C(C=C3)OCOC)OC)OC)OC(C)C

Technology Process of Diethylcarbamic acid 2-[2-methoxy-4-(methoxymethoxy)phenyl]-4-methoxy-5-isopropoxy-1-naphthyl ester

There total 4 articles about Diethylcarbamic acid 2-[2-methoxy-4-(methoxymethoxy)phenyl]-4-methoxy-5-isopropoxy-1-naphthyl ester 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: 99.0%

2-methoxy-4-methoxymethoxyphenylboronic acid (199858-19-0) + N,N-diethyl O-(2-iodo-5-isopropoxy-4-methoxy)-1-naphthylcarbamate (199858-17-8) → N,N-diethyl O-[4-methoxy-5-isopropoxy-2-(2-methoxy-5-methoxymethoxyphenyl)]-1-naphthylcarbamate (199858-21-4)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; barium hydroxide octahydrate; In 1,2-dimethoxyethane; water; for 3h; Inert atmosphere; Reflux;

DOI:10.1021/jo9001454

Reference yield:

4-bromo-3-methoxyphenol (102127-34-4) → N,N-diethyl O-[4-methoxy-5-isopropoxy-2-(2-methoxy-5-methoxymethoxyphenyl)]-1-naphthylcarbamate (199858-21-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 91 percent / NaH / dimethylformamide

2: 72 percent / 1.) n-BuLi; 3.) H₃O(+) / tetrahydrofuran / 1.) -78 deg C

3: 95 percent / Ba(OH)2 / Pd⁽⁰⁾

With barium dihydroxide; n-butyllithium; oxonium; sodium hydride; palladium; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(97)10188-5

Reference yield:

1-bromo-2-methoxy-4-(methoxymethoxy)benzene (949892-17-5) → N,N-diethyl O-[4-methoxy-5-isopropoxy-2-(2-methoxy-5-methoxymethoxyphenyl)]-1-naphthylcarbamate (199858-21-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 72 percent / 1.) n-BuLi; 3.) H₃O(+) / tetrahydrofuran / 1.) -78 deg C

2: 95 percent / Ba(OH)2 / Pd⁽⁰⁾

With barium dihydroxide; n-butyllithium; oxonium; palladium; In tetrahydrofuran;

DOI:10.1016/S0040-4039(97)10188-5

upstream raw materials:

2-methoxy-4-methoxymethoxyphenylboronic acid

N,N-diethyl O-(2-iodo-5-isopropoxy-4-methoxy)-1-naphthylcarbamate

4-bromo-3-methoxyphenol

1-bromo-2-methoxy-4-(methoxymethoxy)benzene

Downstream raw materials:

N,N-diethyl 3-methoxy-5-methoxymethoxy-2-(4-methoxy-5-isopropoxy-1-hydroxynaphth-2-yl)benzamide

defucogilvocarcin V