ethyl 3,6,6-trimethyl-4-oxo-4,5,6,7-tetrahydro-1H-indole-2-carboxylate

Base Information

• Chemical Name: ethyl 3,6,6-trimethyl-4-oxo-4,5,6,7-tetrahydro-1H-indole-2-carboxylate
• CAS No.: 37711-24-3
• Molecular Formula: C₁₄H₁₉NO₃
• Molecular Weight: 249.31
• Hs Code.: 2933990090
• European Community (EC) Number: 833-816-8
• DSSTox Substance ID: DTXSID60368875
• Wikidata: Q82155744
• Mol file: 37711-24-3.mol

Synonyms:ethyl 3,6,6-trimethyl-4-oxo-4,5,6,7-tetrahydro-1H-indole-2-carboxylate;37711-24-3;ethyl 3,6,6-trimethyl-4-oxo-5,7-dihydro-1H-indole-2-carboxylate;SCHEMBL20569319;DTXSID60368875;BBL025749;MFCD06358659;STL377774;AKOS000117382;VS-08078;CS-0451854;FT-0682972;EN300-11147;SR-01000058948;J-520832;SR-01000058948-1;Z57033949;ethyl3,6,6-trimethyl-4-oxo-4,5,6,7-tetrahydro-1H-indole-2-carboxylate;3,6,6-TRIMETHYL-4-OXO-4,5,6,7-TETRAHYDRO-1H-INDOLE-2-CARBOXYLIC ACID ETHYL ESTER;3,6,6-TRIMETHYL-4-OXO-4,5,6,7-TETRAHYDRO-1H-INDOLE-2-CARBOXYLICACIDETHYLESTER

Chemical Property of ethyl 3,6,6-trimethyl-4-oxo-4,5,6,7-tetrahydro-1H-indole-2-carboxylate

Chemical Property:

• Vapor Pressure: 2.39E-07mmHg at 25°C
• Refractive Index: 1.531
• Boiling Point: 422.6 °C at 760 mmHg
• Flash Point: 209.4 °C
• PSA: 59.16000
• Density: 1.132g/cm³
• LogP: 2.65490
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 249.13649347
• Heavy Atom Count: 18
• Complexity: 364

Purity/Quality:

98%Min ^*data from raw suppliers

Ethyl 3,6,6-trimethyl-4-oxo-4,5,6,7-tetrahydro-1H-indole-2-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=C(C2=C(N1)CC(CC2=O)(C)C)C

Technology Process of ethyl 3,6,6-trimethyl-4-oxo-4,5,6,7-tetrahydro-1H-indole-2-carboxylate

There total 4 articles about ethyl 3,6,6-trimethyl-4-oxo-4,5,6,7-tetrahydro-1H-indole-2-carboxylate 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: 65.0%

(E)-2-(5,5-Dimethyl-3-oxo-cyclohex-1-enylamino)-but-2-enoic acid ethyl ester (84033-49-8,84033-50-1) → ethyl 4-oxo-3,6,6-trimethyl-4,5,6,7-tetrahydro-1H-indole-2-carboxylate (37711-24-3)

Guidance literature:

In diethyl ether; for 1h; Irradiation;

DOI:10.1021/jo00233a017

Reference yield:

ethyl acetoacetate (141-97-9) + dimedone (126-81-8) → ethyl 4-oxo-3,6,6-trimethyl-4,5,6,7-tetrahydro-1H-indole-2-carboxylate (37711-24-3)

Guidance literature:

ethyl acetoacetate; With acetic acid; sodium nitrite; In water; at 12 - 20 ℃;

dimedone; With zinc; In water; at 60 ℃; for 3.5h; Reflux;

Reference yield:

dimedone (126-81-8) + ethyl 2-hydroxyimino-3-oxobutanoate (5408-04-8) → ethyl 4-oxo-3,6,6-trimethyl-4,5,6,7-tetrahydro-1H-indole-2-carboxylate (37711-24-3)

Guidance literature:

With sodium acetate; acetic acid; zinc; for 1h; Yield given; Heating;

DOI:10.1021/jo00044a012

upstream raw materials:

dimedone

ethyl 2-hydroxyimino-3-oxobutanoate

(E)-2-(5,5-Dimethyl-3-oxo-cyclohex-1-enylamino)-but-2-enoic acid ethyl ester

ethyl acetoacetate

Downstream raw materials:

3,6,6-trimethyl-4-oxo-4,5,6,7-tetrahydro-1H-indole-2-carboxylic acid

3,6,6-trimethyl-6,7-dihydro-1H-indole-4(5H)-one

Refernces

• 1、 -. "INHIBITORS OF METALLO-BETA-LACTAMASES". Paragraph 00163; 00164. . Retrieved 2018/12/13.
• 2、 Gelas-Mialhe, Yvonne,Mabiala, Gaston,Vessiere, Roger. "Photochemical Heterocyclization of Functionalized Dienamines". . p. 5395 - 5400. Retrieved 2007/10/02.