Benzamide, N,N-diethyl-2-methoxy-6-(2-propenyl)-

Base Information

• Chemical Name: Benzamide, N,N-diethyl-2-methoxy-6-(2-propenyl)-
• CAS No.: 88440-84-0
• Molecular Formula: C15H21NO2
• Molecular Weight: 247.337
• DSSTox Substance ID: DTXSID80461998
• Nikkaji Number: J754.635A
• Wikidata: Q82286462
• Mol file: 88440-84-0.mol

Synonyms:Benzamide, N,N-diethyl-2-methoxy-6-(2-propenyl)-;88440-84-0;DTXSID80461998;2-allyl-N,N-diethyl-6-methoxybenzamide;N,N-diethyl-2-methoxy-6-prop-2-enylbenzamide

Chemical Property of Benzamide, N,N-diethyl-2-methoxy-6-(2-propenyl)-

Chemical Property:

• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 247.157228913
• Heavy Atom Count: 18
• Complexity: 274

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCN(CC)C(=O)C1=C(C=CC=C1OC)CC=C

Technology Process of Benzamide, N,N-diethyl-2-methoxy-6-(2-propenyl)-

There total 1 articles about Benzamide, N,N-diethyl-2-methoxy-6-(2-propenyl)- 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:

N,N-diethyl-2-methoxybenzamide (51674-10-3) + allyl bromide (106-95-6) → N,N-Diethyl-2-allyl-6-methoxybenzamide (88440-84-0)

Guidance literature:

Yield given. Multistep reaction;

DOI:10.1021/jo00179a001

Reference yield: 35.0%

N,N-Diethyl-2-allyl-6-methoxybenzamide (88440-84-0) → 8-methoxy-naphthalen-1-ol (3588-75-8)

Guidance literature:

With methyllithium; In tetrahydrofuran; at -78 - 25 ℃; for 8h;

DOI:10.1021/jo00352a036

Reference yield:

N,N-Diethyl-2-allyl-6-methoxybenzamide (88440-84-0) → (-)-salicylihalamide A (198481-99-1,198482-00-7)

Guidance literature:

Multi-step reaction with 17 steps

1: 65 percent / I₂ / tetrahydrofuran; H₂O / 24 h / 20 °C

2: 73 percent / zinc; acetic acid / 24 h / 90 °C

3: 84 percent / triphenylphosphine; diethyl azodicarboxylate / benzene / 24 h

4: (Cy₃P)2Cl₂Ru=CHPh / CH₂Cl₂ / 0.67 h / 20 °C

5: 98 percent / DDQ; buffer / CH₂Cl₂; H₂O / 0.75 h / 20 °C / pH 7

6: 98 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 20 °C

7: 82 percent / BBr₃ / CH₂Cl₂ / 3 h / -78 °C

8: 97 percent / sodium chlorite; NaH₂PO₄*2H₂O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 1 h

9: triethylamine / CH₂Cl₂ / 2 h / 20 °C

10: 21 mg / K₂CO₃; H₂O / methanol; tetrahydrofuran / 0.08 h / 20 °C

11: N,N-diisopropylethylamine / acetone / 0 - 20 °C

12: sodium azide / acetone; H₂O / 0.5 h / 20 °C

13: toluene / 0.25 h / 110 °C

14: 21.6 mg / toluene / 0.17 h / Heating

15: 81 percent / sodium bis(trimethylsilyl)amide / tetrahydrofuran; benzene / 0.17 h / 0 °C

16: tetrabutylammonium fluoride / tetrahydrofuran / 0.17 h / 0 °C

17: 2.6 mg / HF*py / tetrahydrofuran; pyridine / 48 h / 20 °C

With sodium chlorite; sodium dihydrogenphosphate; sodium azide; 2-methyl-but-2-ene; tetrabutyl ammonium fluoride; water; iodine; sodium hexamethyldisilazane; boron tribromide; potassium carbonate; Dess-Martin periodane; pyridine hydrogenfluoride; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc; diethylazodicarboxylate; Grubbs catalyst first generation; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; acetone; toluene; tert-butyl alcohol; benzene; 3: Mitsunobu esterification / 4: ring closing metathesis / 6: Dess-Martin oxidation / 13: Curtius rearrangement;

DOI:10.1016/S0040-4020(02)00657-9

upstream raw materials:

N,N-diethyl-2-methoxybenzamide

allyl bromide

Downstream raw materials:

8-methoxy-naphthalen-1-ol

(-)-salicylihalamide A

2-allyl-6-methoxy-benzoic acid

2-Allyl-6-methoxy-benzoic acid (R)-1-[2-(4-methoxy-benzyloxy)-ethyl]-hept-6-enyl ester