3-Isochromanone

Base Information

• Chemical Name: 3-Isochromanone
• CAS No.: 4385-35-7
• Molecular Formula: C9H8O2
• Molecular Weight: 148.161
• Hs Code.: 2932999099
• European Community (EC) Number: 224-493-9
• NSC Number: 160530
• UNII: 4J87XDF6HE
• DSSTox Substance ID: DTXSID00195960
• Nikkaji Number: J13.284E
• Wikidata: Q72445602
• Metabolomics Workbench ID: 67943
• ChEMBL ID: CHEMBL447815
• Mol file: 4385-35-7.mol

Synonyms:3-Isochromanone;4385-35-7;isochroman-3-one;1,4-Dihydro-3H-2-benzopyran-3-one;1,4-dihydroisochromen-3-one;3H-2-Benzopyran-3-one, 1,4-dihydro-;3,4-dihydro-1H-2-benzopyran-3-one;3-lsochroManone;1H-2-Benzopyran-3(4H)-one;MFCD00043005;EINECS 224-493-9;NSC-160530;2-Hydroxymethylphenylacetic acid lactone;isochromanone, 4a;SBB068599;3-Isochromanone, 98%;bmse000539;4J87XDF6HE;SCHEMBL724064;CHEMBL447815;BDBM23985;ILHLUZUMRJQEAH-UHFFFAOYSA-;DTXSID00195960;1,4-Dihydro-3H-isochromen-3-one;BCP25778;1,4-dihydro-3H-isochromene-3-one;3,6-Dihydro-4,5-benzo-2-pyrone;3H-2-Benzopyran-3-one,4-dihydro-;NSC160530;1,4-Dihydro-3H-isochromen-3-one #;AKOS004907726;CS-W016337;GS-6820;NSC 160530;AM803908;SY036247;FT-0635258;I0544;C07728;EN300-103986;A826436;J-511161;Z1255486033

Chemical Property of 3-Isochromanone

Chemical Property:

• Appearance/Colour: WHITE CRYSTALLINE POWDER
• Vapor Pressure: 0.000144mmHg at 25°C
• Melting Point: 80-82 °C(lit.)
• Refractive Index: 1.562
• Boiling Point: 332.6 °C at 760 mmHg
• Flash Point: 137.7 °C
• PSA: 26.30000
• Density: 1.196 g/cm³
• LogP: 1.28590
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform (Slightly, Heated, Sonicated), Methanol (Slightly)
• Water Solubility.: 易溶于丙酮,甲醇,二氯乙烷等有机溶剂
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 148.052429494
• Heavy Atom Count: 11
• Complexity: 165

Purity/Quality:

99% ^*data from raw suppliers

3-Isochromanone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

Useful:

• Canonical SMILES: C1C2=CC=CC=C2COC1=O
• General Description: 3-Isochromanone is a heterocyclic organic compound featuring a benzene ring fused to a six-membered lactone structure. It serves as a key intermediate in the synthesis of various pharmaceuticals and bioactive molecules due to its versatile reactivity. 3-ISOCHROMANONE's structure allows for functionalization at multiple positions, making it valuable in medicinal chemistry and materials science. Its derivatives have been explored for potential biological activities, including antimicrobial and anti-inflammatory properties. The lactone moiety in 3-isochromanone also contributes to its utility in polymer and fragrance applications.

Technology Process of 3-Isochromanone

There total 77 articles about 3-Isochromanone 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: 100.0%

carbon monoxide (201230-82-2) + (2-(bromomethyl)phenyl)methanol (74785-02-7) → isochroman-3-one (4385-35-7)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; C₅₂H₄₆O₂P₂Pd₂; triphenylphosphine; In toluene; at 60 ℃; for 2.16667h; under 760.051 Torr; Conversion of starting material;

Reference yield: 95.1%

α,α'-dibromo-o-xylene (91-13-4) → isochroman-3-one (4385-35-7)

Guidance literature:

In tert-butyl alcohol;

Reference yield: 95.0%

α-chloro-α'-cyano-o-xylene (98590-71-7) → isochroman-3-one (4385-35-7) + α-hydroxy-α'-cyano-o-xylene (67519-22-6)

Guidance literature:

With hydrogenchloride; In water; at 150 ℃; for 3h; under 3677.86 Torr;

upstream raw materials:

3H-3,8A-methano-benzo[c][1,2]dioxin

1-methyl-4-nitrosobenzene

(2-methoxymethyl-phenyl)-acetonitrile

(2-methoxymethyl-phenyl)-acetyl chloride

Downstream raw materials:

(E)-2-[2-[3-[2-[4-(cyclobutyl)-2-thiazolyl]ethenyl]phenylamino]-2-oxoethyl]benzyl alcohol

picoxystrobin

(E)-methyl 2-[2-(6-trifluoromethylpyrid-2-yloxymethyl)phenyl]-3-hydroxyacrylate

2-[6-(trifluoromethyl)-2-pyridyloxymethyl]phenylacetic acid methyl ester

Refernces

Studies of reactions of o-xylylene-α,α′-dihalides with palladium complexes and the catalytic synthesis of 3-isochromanone

10.1016/j.jorganchem.2006.01.029

The study focuses on the homogeneous catalysis by palladium complexes with phosphorus(III) ligands for the carbonylation of o-xylylene dihalides in the presence of water to form 3-isochromanone, an important synthetic intermediate for pharmaceutical and agrochemical products. Key chemicals used in the study include o-xylylene dihalides, palladium complexes, and triphenylphosphine (PPh3) as the most effective catalyst. The purpose of these chemicals is to investigate the catalytic efficiency and to understand the byproducts and intermediates formed during the reaction. The study also explores the role of excess PPh3 in prolonging the catalyst's activity and its transformation to bis-phosphonium compounds, which have been investigated for their impact on the catalytic process. The research aims to shed light on the mechanism and side reactions of lactone formation, contributing to the optimization of the catalytic synthesis of 3-isochromanone.

TANDEM ELECTROCYCLIC-SIGMATROPIC REACTION OF BENZOCYCLOBUTENES. 2. A NEW ROUTE TO ISOCHROMAN-3-ONE-4-SPIRO-1'-CYCLOALK-3'-ENES

10.1016/S0040-4039(00)84151-9

The research describes a novel synthetic methodology for constructing spiro-fused isochroman-3-one derivatives, which are potentially useful as synthons for natural products such as Amaryllidaceae alkaloids. The study focuses on the tandem electrocyclic-sigmatropic reaction of benzocyclobutenylspirolactones, derived from 1-cyano-5-methoxybenzocyclobutene, to yield isochroman-3-one-4-spiro-1'-cycloalk-3'-enes in good yields. The process involves a series of chemical reactions, including alkylation, acid hydrolysis, basic hydrolysis, and acid treatment, utilizing chemicals such as LDA (lithium diisopropylamide), vinylmagnesium bromide, and various dioxolane derivatives. The conclusions of the research highlight the efficiency of this method in providing a unique route to合成spirocyclic compounds, with applications in the synthesis of Amaryllidaceae alkaloids currently underway.