7-Chloroindeno[1,2-e][1,3,4]oxadiazine-2,4a(3h,5h)-dicarboxylic acid 4a-methyl 2-benzyl ester

Base Information

• Chemical Name: 7-Chloroindeno[1,2-e][1,3,4]oxadiazine-2,4a(3h,5h)-dicarboxylic acid 4a-methyl 2-benzyl ester
• CAS No.: 170917-89-2
• Molecular Formula: C20H17ClN2O5
• Molecular Weight: 400.818
• European Community (EC) Number: 605-595-6
• DSSTox Substance ID: DTXSID601120970
• Mol file: 170917-89-2.mol

Synonyms:170917-89-2;7-Chloroindeno[1,2-e][1,3,4]oxadiazine-2,4a(3h,5h)-dicarboxylic acid 4a-methyl 2-benzyl ester;2-O-benzyl 4a-O-methyl 7-chloro-3,5-dihydroindeno[1,2-e][1,3,4]oxadiazine-2,4a-dicarboxylate;SCHEMBL9238508;DTXSID601120970;4a-Methyl 2-(phenylmethyl) 7-chloroindeno[1,2-e][1,3,4]oxadiazine-2,4a(3H,5H)-dicarboxylate

Chemical Property of 7-Chloroindeno[1,2-e][1,3,4]oxadiazine-2,4a(3h,5h)-dicarboxylic acid 4a-methyl 2-benzyl ester

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 122-125℃
• PSA: 85.89000
• Density: 1.41
• LogP: 2.71620
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 400.0825993
• Heavy Atom Count: 28
• Complexity: 651

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C12CC3=C(C1=NN(CO2)C(=O)OCC4=CC=CC=C4)C=CC(=C3)Cl

Technology Process of 7-Chloroindeno[1,2-e][1,3,4]oxadiazine-2,4a(3h,5h)-dicarboxylic acid 4a-methyl 2-benzyl ester

There total 4 articles about 7-Chloroindeno[1,2-e][1,3,4]oxadiazine-2,4a(3h,5h)-dicarboxylic acid 4a-methyl 2-benzyl 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: 95.9%

formaldehyde diethyl acetal (462-95-3) + C19H17ClN2O5 (173903-19-0) → 7?chloro-2H,3H,4aH,5H-indeno[1,2-e][1,3,4]oxadiazine?2,4a-dicarboxylic acid 4a-methyl 2?benzyl ester (170917-89-2)

Guidance literature:

In toluene; at 110 ℃;

Reference yield: 92.5%

formaldehyde diethyl acetal (462-95-3) + N-benzyloxycarbonyl-hydrazine (5331-43-1) + (R,S)‐5‐chloro‐1‐oxo‐2,3‐dihydro‐2‐hydroxy‐1H‐indene‐2‐carboxylic acid methyl ester (144172-24-7) → 7?chloro-2H,3H,4aH,5H-indeno[1,2-e][1,3,4]oxadiazine?2,4a-dicarboxylic acid 4a-methyl 2?benzyl ester (170917-89-2)

Guidance literature:

N-benzyloxycarbonyl-hydrazine; (R,S)‐5‐chloro‐1‐oxo‐2,3‐dihydro‐2‐hydroxy‐1H‐indene‐2‐carboxylic acid methyl ester; With phosphorus pentoxide; In 5,5-dimethyl-1,3-cyclohexadiene; at 50 ℃; for 3h;

formaldehyde diethyl acetal; In 5,5-dimethyl-1,3-cyclohexadiene; at 140 ℃; Temperature;

Reference yield: 88.0%

C12H11ClN2O3 (173903-23-6) + benzyl chloroformate (501-53-1,94274-21-2) → 7?chloro-2H,3H,4aH,5H-indeno[1,2-e][1,3,4]oxadiazine?2,4a-dicarboxylic acid 4a-methyl 2?benzyl ester (170917-89-2)

Guidance literature:

With dimethylbromosulphonium bromide; In toluene; at 20 ℃; for 0.25h;

DOI:10.1080/00397911.2010.497592

upstream raw materials:

C₁₂H₁₁ClN₂O₃

benzyl chloroformate

formaldehyde diethyl acetal

N-benzyloxycarbonyl-hydrazine

Refernces

• 1、 -. "Preparation method of indoxacarb key intermediate". Paragraph 0007; 0025-0026; 0028-0032; 0034-0038; 0040-0044. . Retrieved 2020/11/05.
• 2、 Shailaja,Manjula,Vittal Rao. "Bromodimethyl sulfonium bromide mediated rapid and facile protection of amines". experimental part. p. 2073 - 2080. Retrieved 2011/07/31.