2,2'-Spirobi[indene]-1,1'(3H,3'H)-dione

Base Information

• Chemical Name: 2,2'-Spirobi[indene]-1,1'(3H,3'H)-dione
• CAS No.: 37558-43-3
• Molecular Formula: C₁₇H₁₂O₂
• Molecular Weight: 248.281
• DSSTox Substance ID: DTXSID60560094
• Nikkaji Number: J1.838.317I,J3.305.284G,J3.305.285E
• Wikidata: Q82443079
• Mol file: 37558-43-3.mol

Synonyms:2,2'-Spirobi[indene]-1,1'(3H,3'H)-dione;37558-43-3;2,2'-spirobi[3H-indene]-1,1'-dione;53110-88-6;(-)-2,2\'-Spirobiindane-1,1\'-dione;2,2'-Spirobiindan-1,1'-dion;DTXSID60560094

Chemical Property of 2,2'-Spirobi[indene]-1,1'(3H,3'H)-dione

Chemical Property:

• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 248.083729621
• Heavy Atom Count: 19
• Complexity: 385

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2=CC=CC=C2C(=O)C13CC4=CC=CC=C4C3=O

Technology Process of 2,2'-Spirobi[indene]-1,1'(3H,3'H)-dione

There total 72 articles about 2,2'-Spirobi[indene]-1,1'(3H,3'H)-dione 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: 94.0%

2,2'-Spirobiindan-1-on (40932-30-7) → 2,2'-spirobiindan-1,1'-dione (61895-27-0,37558-43-3,52485-37-7,53110-88-6)

Guidance literature:

With 2,2-dimethylbutyric acid; C₂₈H₃₄F₆MnN₆O₆S₂; dihydrogen peroxide; In dichloromethane; acetonitrile; at -30 ℃; for 2h; enantioselective reaction; Inert atmosphere; Schlenk technique;

DOI:10.1021/acscatal.7b03601

Reference yield: 92.0%

2-(2-methoxycarbonylbenzyl)-1-oxoindan-2-carboxylic acid ethyl ester (846589-63-7) → 2,2'-spirobiindan-1,1'-dione (61895-27-0,37558-43-3,52485-37-7,53110-88-6)

Guidance literature:

With hydrogen bromide; In acetic acid; for 3.25h; Heating;

DOI:10.1016/j.tet.2004.10.044

Reference yield: 90.0%

phenyl 2-((1-oxo-2,3-dihydro-1H-inden-2-yl)methyl)benzoate → 2,2'-spirobiindan-1,1'-dione (61895-27-0,37558-43-3,52485-37-7,53110-88-6)

Guidance literature:

With tetrabutylammomium bromide; In toluene; at 20 ℃; for 16h; Alkaline conditions;

DOI:10.1002/anie.201607731

upstream raw materials:

dibenzylmalonic acid

2-((1-oxo-2,3-dihydro-1H-inden-2-yl)methyl)benzoic acid

dibenzylmalonyl Dichloride

2-Benzyl-3-(2-carboxyphenyl)-propansaeure

Downstream raw materials:

2-((1-oxo-2,3-dihydro-1H-inden-2-yl)methyl)benzoic acid

1'-benzyl-1-hydroxy-2,2'-spirobiindan-1-one

(-)-2,2'-Spirobiindan-1,1'-dione

(+)-(2S)-2,2'-spirobiindane-1,1'-dione