2,2-Dimethyl-5-{[(4-methylbenzene-1-sulfonyl)oxy]imino}-1,3-dioxane-4,6-dione

Base Information

• Chemical Name: 2,2-Dimethyl-5-{[(4-methylbenzene-1-sulfonyl)oxy]imino}-1,3-dioxane-4,6-dione
• CAS No.: 215436-24-1
• Molecular Formula: C13H13NO7S
• Molecular Weight: 327.315
• DSSTox Substance ID: DTXSID30444534
• Nikkaji Number: J1.051.326J
• Mol file: 215436-24-1.mol

Synonyms:215436-24-1;DTXSID30444534;2,2-Dimethyl-5-(tosyloxyimino)-1,3-dioxane-4,6-dione;2,2-Dimethyl-5-{[(4-methylbenzene-1-sulfonyl)oxy]imino}-1,3-dioxane-4,6-dione

Chemical Property of 2,2-Dimethyl-5-{[(4-methylbenzene-1-sulfonyl)oxy]imino}-1,3-dioxane-4,6-dione

Chemical Property:

• Melting Point: 155-156 °C
• Boiling Point: 417.4±38.0 °C(Predicted)
• PSA: 116.71000
• Density: 1.44±0.1 g/cm3(Predicted)
• LogP: 1.97320
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 3
• Exact Mass: 327.04127293
• Heavy Atom Count: 22
• Complexity: 572

Purity/Quality:

99% ^*data from raw suppliers

5-(TOSYLOXYIMINO)-2,2-DIMETHYL-1,3-DIOXANE-4,6-DIONE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)ON=C2C(=O)OC(OC2=O)(C)C

Technology Process of 2,2-Dimethyl-5-{[(4-methylbenzene-1-sulfonyl)oxy]imino}-1,3-dioxane-4,6-dione

There total 2 articles about 2,2-Dimethyl-5-{[(4-methylbenzene-1-sulfonyl)oxy]imino}-1,3-dioxane-4,6-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: 79.0%

p-toluenesulfonyl chloride (98-59-9) + 5-hydroxyimino-2,2-dimethyl-1,3-dioxane-4,6-dione sodium salt → 2,2-dimethyl-5-(p-tosyloxyimino)-1,3-dioxane-4,6-dione (215436-24-1)

Guidance literature:

In acetone; at 20 ℃; for 5h;

DOI:10.3987/COM-99-S22

Reference yield: 59.0%

cycl-isopropylidene malonate (2033-24-1) + p-toluenesulfonyl chloride (98-59-9) → 2,2-dimethyl-5-(p-tosyloxyimino)-1,3-dioxane-4,6-dione (215436-24-1)

Guidance literature:

cycl-isopropylidene malonate; With sodium nitrite; In methanol; water; at 20 ℃; for 2h; Inert atmosphere;

p-toluenesulfonyl chloride; In methanol; aq. phosphate buffer; water; at 0 ℃; for 0.55h; pH=7; Inert atmosphere;

DOI:10.15227/orgsyn.080.0133

Reference yield: 90.0%

2,2-dimethyl-5-(p-tosyloxyimino)-1,3-dioxane-4,6-dione (215436-24-1) + isoprene (78-79-5,9003-31-0) → Toluene-4-sulfonic acid 3,9,9-trimethyl-7,11-dioxo-8,10-dioxa-1-aza-spiro[5.5]undec-3-en-1-yl ester (768368-54-3)

Guidance literature:

With dimethylaluminum chloride; In hexane; dichloromethane; at -78 ℃; for 4h;

DOI:10.1021/jo981014e

upstream raw materials:

cycl-isopropylidene malonate

p-toluenesulfonyl chloride

Downstream raw materials:

Toluene-4-sulfonic acid 5,9,9-trimethyl-7,11-dioxo-8,10-dioxa-1-aza-spiro[5.5]undec-3-en-1-yl ester

Toluene-4-sulfonic acid 3-tert-butyl-9,9-dimethyl-7,11-dioxo-8,10-dioxa-1-aza-spiro[5.5]undec-3-en-1-yl ester

Toluene-4-sulfonic acid 3-butyl-9,9-dimethyl-7,11-dioxo-8,10-dioxa-1-aza-spiro[5.5]undec-3-en-1-yl ester

Toluene-4-sulfonic acid 3,5,9,9-tetramethyl-7,11-dioxo-8,10-dioxa-1-aza-spiro[5.5]undec-3-en-1-yl ester