methyl (3S)-2,3-dihydro-1,4-benzodioxine-3-carboxylate

Base Information

• Chemical Name: methyl (3S)-2,3-dihydro-1,4-benzodioxine-3-carboxylate
• CAS No.: 650597-66-3
• Molecular Formula: C₁₀H₁₀O₄
• Molecular Weight: 194.187
• DSSTox Substance ID: DTXSID40352797
• Nikkaji Number: J1.995.252E
• Wikidata: Q82130154
• Mol file: 650597-66-3.mol

Synonyms:650597-66-3;methyl (3S)-2,3-dihydro-1,4-benzodioxine-3-carboxylate;(S)-2,3-Dihydro-1,4-benzodioxin-2-carboxylic acid methyl ester;AC1LEG1Z;DTXSID40352797

Chemical Property of methyl (3S)-2,3-dihydro-1,4-benzodioxine-3-carboxylate

Chemical Property:

• PSA: 44.76000
• LogP: 0.99940
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 194.05790880
• Heavy Atom Count: 14
• Complexity: 216

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC(=O)C1COC2=CC=CC=C2O1
• Isomeric SMILES: COC(=O)[C@@H]1COC2=CC=CC=C2O1
• Uses: Methyl 2,?3-?dihydro-?1,?4-?benzodioxin-?2-?carboxylic Acid is used as a Reactant in the preparation of benzo-fused heterocycle sulfamide derivatives from chroman-2-carboxylic acid via amination and condensation reactions and their use for the treatment of pain.

Technology Process of methyl (3S)-2,3-dihydro-1,4-benzodioxine-3-carboxylate

There total 30 articles about methyl (3S)-2,3-dihydro-1,4-benzodioxine-3-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: 98.0%

methyl benzo[b][1,4]dioxine-2-carboxylate → (R)-methyl 2,3-dihydrobenzo[b][1,4]dioxine-2-carboxylate (650597-66-3)

Guidance literature:

With bis(norbornadiene)rhodium(l)tetrafluoroborate; C₄₆H₃₈F₆FeN₂P₂S; hydrogen; In dichloromethane; at 25 ℃; for 12h; under 7600.51 Torr; Reagent/catalyst; Pressure; Temperature; Solvent; enantioselective reaction; Catalytic behavior; Autoclave;

DOI:10.1021/acs.orglett.8b01469

Reference yield: 97.0%

methanol (67-56-1) + 1,4-benzodioxane-2-carboxylic acid (3663-80-7,34385-93-8,70918-53-5,70918-54-6) → methyl 2,3-dihydrobenzo[b][1,4]dioxine-2-carboxylate (3663-79-4,650597-66-3)

Guidance literature:

With sulfuric acid; for 1h; Heating;

DOI:10.1021/jm00128a049

Reference yield: 92.0%

Methyl 2,3-dibromopropionate (1729-67-5) + benzene-1,2-diol (120-80-9,19481-10-8,37349-32-9) → methyl 2,3-dihydrobenzo[b][1,4]dioxine-2-carboxylate (3663-79-4,650597-66-3)

Guidance literature:

With potassium carbonate; In acetone; for 18h; Reflux;

DOI:10.1021/acs.orglett.8b01469

upstream raw materials:

methanol

1,4-benzodioxane-2-carboxylic acid

2-cyano-1,4-benzodioxane

benzene-1,2-diol

Refernces

• 1、 Yin, Xuguang,Huang, Yi,Chen, Ziyi,Hu, Yang,Tao, Lin,Zhao, Qingyang,Dong, Xiu-Qin,Zhang, Xumu. "Enantioselective Access to Chiral 2-Substituted 2,3-Dihydrobenzo[1,4]dioxane Derivatives through Rh-Catalyzed Asymmetric Hydrogenation". supporting information. p. 4173 - 4177. Retrieved 2018/07/29.
• 2、 Bolchi, Cristiano,Valoti, Ermanno,Straniero, Valentina,Ruggeri, Paola,Pallavicini, Marco. "From 2-aminomethyl-1,4-benzodioxane enantiomers to unichiral 2-cyano- and 2-carbonyl-substituted benzodioxanes via dichloroamine". . p. 6732 - 6737. Retrieved 2014/08/05.