(Z)-3-ethylideneisobenzofuran-1(3H)-one

Base Information

• Chemical Name: (Z)-3-ethylideneisobenzofuran-1(3H)-one
• CAS No.: 4767-62-8
• Molecular Formula: C10H8O2
• Molecular Weight: 160.172
• DSSTox Substance ID: DTXSID301277338
• Nikkaji Number: J558.398E,J915.796D
• ChEMBL ID: CHEMBL401202
• Mol file: 4767-62-8.mol

Synonyms:3-ethylidenephthalide;(Z)-3-ethylideneisobenzofuran-1(3H)-one;61658-90-0;3-Aethylidenphthalid;3-Ethylideneisobenzofuranone;CHEMBL401202;SCHEMBL2606686;DTXSID301277338;STK530917;3-Ethylidene-1(3H)-isobenzofuranone;AKOS005463401;(3Z)-3-Ethylidene-1(3H)-isobenzofuranone;3-Eth-(Z)-ylidene-3H-isobenzofuran-1-one;(3Z)-3-Ethylidene-2-benzofuran-1(3H)-one;(3Z)-3-Ethylidene-2-benzofuran-1(3H)-one #;4767-62-8

Chemical Property of (Z)-3-ethylideneisobenzofuran-1(3H)-one

Chemical Property:

• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 160.052429494
• Heavy Atom Count: 12
• Complexity: 230

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC=C1C2=CC=CC=C2C(=O)O1
• Isomeric SMILES: C/C=C\1/C2=CC=CC=C2C(=O)O1

Technology Process of (Z)-3-ethylideneisobenzofuran-1(3H)-one

There total 2 articles about (Z)-3-ethylideneisobenzofuran-1(3H)-one 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: 35.0%

Allyl acetate (591-87-7) + benzoic acid (65-85-0,8013-63-6) → (3Z)-3-Ethylidene-7-((E)-prop-1-enyl) isobenzofuran-1(3H)-one + 3-(Z)-(methylmethylene)-1(3H)-isobenzofuranone (4767-62-8)

Guidance literature:

With [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; potassium carbonate; In N,N-dimethyl-formamide; at 100 ℃; for 12h; regioselective reaction; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.orglett.8b00533

Reference yield:

methanol (67-56-1) + carbon monoxide (201230-82-2) + 1-(2-iodophenyl)-2-propen-1-ol (148761-93-7) → methyl 2-propionylbenzoate (32025-37-9) + 3-(Z)-(methylmethylene)-1(3H)-isobenzofuranone (4767-62-8) + (E)-3-ethylidene-1-isobenzofuranone (4767-63-9) + (3aR*,8bS*)-3,3a-dihydro-2H-indeno[1,2-b]furan-2,4(8bH)-dione

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; triethylamine; In acetonitrile; benzene; at 100 ℃; for 20h; under 30400 Torr; Yields of byproduct given;

DOI:10.1021/ja9533196

Reference yield:

3-(Z)-(methylmethylene)-1(3H)-isobenzofuranone (4767-62-8) → 2-Propionyl-benzoic acid anion

Guidance literature:

With water; In 1,4-dioxane; at 30 ℃; Rate constant; base-catalysed hydrolysis;

DOI:10.1002/(SICI)1099-1395(199711)10:11<841::AID-PCA950>3.0.CO;2-6

upstream raw materials:

methanol

carbon monoxide

1-(2-iodophenyl)-2-propen-1-ol

Allyl acetate