Isoprothiolane sulfoxide

Base Information

• Chemical Name: Isoprothiolane sulfoxide
• CAS No.: 52303-69-2
• Molecular Formula: C₁₂H₁₈O₅S₂
• Molecular Weight: 306.404
• DSSTox Substance ID: DTXSID80897278
• Nikkaji Number: J532.823C
• Wikidata: Q27107004
• Metabolomics Workbench ID: 53237
• Mol file: 52303-69-2.mol

Synonyms:Isoprothiolane sulfoxide;52303-69-2;Propanedioic acid, 1,3-dithiolan-2-ylidene-, bis(1-methylethyl) ester, 5-oxide;Bis(1-methylethyl) 1,3-dithiolan-2-ylidenepropanedioate 5-oxide;dipropan-2-yl 2-(1-oxo-1,3-dithiolan-2-ylidene)propanedioate;diisopropyl (1-oxido-1,3-dithiolan-2-ylidene)malonate;di(propan-2-yl) (1-oxo-1lambda(4),3-dithiolan-2-ylidene)propanedioate;2-[1,3-dioxo-1,3-bis(propan-2-yloxy)propan-2-ylidene]-1,3-dithiolan-1-ium-1-olate;CHEBI:6048;SCHEMBL11616666;DTXSID80897278;C12H18O5S2;C12-H18-O5-S2;diisopropyl 1-oxo-1,3-dithiolan-2-ylidenemalonate;Q27107004;Propanedioic acid, 2-(1-oxido-1,3-dithiolan-2-ylidene)-, bis(1-methylethyl) ester

Chemical Property of Isoprothiolane sulfoxide

Chemical Property:

• Vapor Pressure: 2.69E-07mmHg at 25°C
• Boiling Point: 421°Cat760mmHg
• Flash Point: 208.4°C
• Density: 1.31g/cm³
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 6
• Exact Mass: 306.05956602
• Heavy Atom Count: 19
• Complexity: 402

Purity/Quality:

98.5% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)OC(=O)C(=C1SCCS1=O)C(=O)OC(C)C

Technology Process of Isoprothiolane sulfoxide

There total 3 articles about Isoprothiolane sulfoxide 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: 65.0%

isoprothiolane (50512-35-1) → Diisopropyl 1,3-dithiolan-2-ylidenemalonate 1-oxide (52303-69-2,108114-60-9,108114-61-0)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; for 2h; Ambient temperature;

DOI:10.1248/cpb.38.3242

Reference yield:

C26H42O11S4 (147848-84-8) → Diisopropyl 1,3-dithiolan-2-ylidenemalonate 1-oxide (52303-69-2,108114-60-9,108114-61-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 5 percent / Na₂CO₃ / methanol; H₂O / 12 h / Ambient temperature

2: 65 percent / m-chloroperbenzoic acid (MCPBA) / CH₂Cl₂ / 12 h / Ambient temperature

With sodium carbonate; 3-chloro-benzenecarboperoxoic acid; In methanol; dichloromethane; water;

Reference yield:

3-{2-[2-(2,2-Bis-isopropoxycarbonyl-1-methoxy-vinylsulfanyl)-ethyldisulfanyl]-ethylsulfanyl}-2-isopropoxycarbonyl-3-methoxy-acrylic acid isopropyl ester (147848-85-9) → Diisopropyl 1,3-dithiolan-2-ylidenemalonate 1-oxide (52303-69-2,108114-60-9,108114-61-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 64 percent / NaBH₄ / methanol; tetrahydrofuran / 1.) 3 d, room temperature, 2.) 2 h, reflux

2: 65 percent / m-chloroperbenzoic acid (MCPBA) / CH₂Cl₂ / 12 h / Ambient temperature

With sodium tetrahydroborate; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane;

upstream raw materials:

isoprothiolane

3-{2-[2-(2,2-Bis-isopropoxycarbonyl-1-methoxy-vinylsulfanyl)-ethyldisulfanyl]-ethylsulfanyl}-2-isopropoxycarbonyl-3-methoxy-acrylic acid isopropyl ester

C₂₆H₄₂O₁₁S₄

Downstream raw materials:

isoprothiolane

3-{2-[2-(2,2-Bis-isopropoxycarbonyl-1-methoxy-vinylsulfanyl)-ethyldisulfanyl]-ethylsulfanyl}-2-isopropoxycarbonyl-3-methoxy-acrylic acid isopropyl ester

Refernces

• 1、 Katagiri,Ise,Watanabe,Kaneko. "Synthesis of nucleosides and related compounds. XVII. Dialkyl 1,3-dithiethan- and 1,3-dithiolan-2-ylidenemalonate S-oxides: Equivalents to dialkoxycarbonylketenes". . p. 3242 - 3248. Retrieved 2007/10/02.