Spiro[benzofuran-2(4H),1'-cyclohexane]-2',4,6'-trione, 3,5,6,7-tetrahydro-4',4',6,6-tetramethyl-

Base Information

• Chemical Name: Spiro[benzofuran-2(4H),1'-cyclohexane]-2',4,6'-trione, 3,5,6,7-tetrahydro-4',4',6,6-tetramethyl-
• CAS No.: 1984-51-6
• Molecular Formula: C₁₇H₂₂O₄
• Molecular Weight: 290.359
• DSSTox Substance ID: DTXSID501119259
• Nikkaji Number: J108.224H
• ChEMBL ID: CHEMBL1598489
• Mol file: 1984-51-6.mol

Synonyms:1984-51-6;3,5,6,7-Tetrahydro-4',4',6,6-tetramethylspiro[benzofuran-2(4H),1'-cyclohexane]-2',4,6'-trione;Spiro[benzofuran-2(4H),1'-cyclohexane]-2',4,6'-trione, 3,5,6,7-tetrahydro-4',4',6,6-tetramethyl-;Oprea1_504468;MLS000108971;CHEMBL1598489;DTXSID501119259;HMS2165H13;HMS3309D10;AKOS024286016;SMR000104919;SR-01000220241;SR-01000220241-1

Chemical Property of Spiro[benzofuran-2(4H),1'-cyclohexane]-2',4,6'-trione, 3,5,6,7-tetrahydro-4',4',6,6-tetramethyl-

Chemical Property:

• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 290.15180918
• Heavy Atom Count: 21
• Complexity: 572

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1(CC2=C(CC3(O2)C(=O)CC(CC3=O)(C)C)C(=O)C1)C

Technology Process of Spiro[benzofuran-2(4H),1'-cyclohexane]-2',4,6'-trione, 3,5,6,7-tetrahydro-4',4',6,6-tetramethyl-

There total 7 articles about Spiro[benzofuran-2(4H),1'-cyclohexane]-2',4,6'-trione, 3,5,6,7-tetrahydro-4',4',6,6-tetramethyl- 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: 90.0%

3-hydroxy-2-[(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-en-1-yl)methyl]-5,5-dimethylcyclohex-2-en-1-one (7599-99-7) → 3,3,10,10-tetramethyldispiro[5.0.57.16]tridecane-1,5,8,12-tetraone (54283-18-0) + 4',4',6,6-tetramethyl-3,5,6,7-tetrahydro-4H-spiro[1-benzofuran-2,1'-cyclohexane]-2',4,6'-trione (1984-51-6)

Guidance literature:

With manganese(III) triacetate dihydrate; In formic acid; at 20 ℃; for 0.0833333h; Inert atmosphere;

DOI:10.1016/j.tet.2020.131165

Reference yield: 79.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + dimedone (126-81-8) → 4',4',6,6-tetramethyl-3,5,6,7-tetrahydro-4H-spiro[1-benzofuran-2,1'-cyclohexane]-2',4,6'-trione (1984-51-6)

Guidance literature:

With dmap; iodine; at 20 ℃; for 1h; chemospecific reaction; Neat (no solvent); Mechanical ball-milling;

DOI:10.1021/ol900451d

Reference yield: 69.0%

3-hydroxy-2-[(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-en-1-yl)methyl]-5,5-dimethylcyclohex-2-en-1-one (7599-99-7) → 4',4',6,6-tetramethyl-3,5,6,7-tetrahydro-4H-spiro[1-benzofuran-2,1'-cyclohexane]-2',4,6'-trione (1984-51-6)

Guidance literature:

With manganese(III) triacetate dihydrate; In acetic acid; for 0.0333333h; Reflux;

DOI:10.1016/j.tet.2020.131165

upstream raw materials:

methanol

dimedone

formaldehyd

3-hydroxy-2-[(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-en-1-yl)methyl]-5,5-dimethylcyclohex-2-en-1-one

Refernces

• 1、 Hisano, Kazuki,Nishikawa, Satomi,Nishino, Hiroshi,Shibuya, Keisuke,Yokote, Suzuka. "Selective synthesis of spiro and dispiro compounds using Mn(III)-based oxidation of tetracarbonyl compounds". . . Retrieved 2020/04/21.
• 2、 Wang, Guan-Wu,Gao, Jie. "Selective formation of spiro dihydrofurans and cyclopropanes through unexpected reaction of aldehydes with 1,3-dicarbonyl compounds". supporting information; experimental part. p. 2385 - 2388. Retrieved 2009/10/10.