1,3-Dioxepane, 2-phenyl-

Base Information

• Chemical Name: 1,3-Dioxepane, 2-phenyl-
• CAS No.: 2749-68-0
• Molecular Formula: C11H14O2
• Molecular Weight: 178.231
• DSSTox Substance ID: DTXSID80450024
• Nikkaji Number: J1.801.813F
• Wikidata: Q82269593
• Mol file: 2749-68-0.mol

Synonyms:1,3-Dioxepane, 2-phenyl-;2-phenyl-1,3-dioxepane;2749-68-0;SCHEMBL2045490;DTXSID80450024

Chemical Property of 1,3-Dioxepane, 2-phenyl-

Chemical Property:

• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 178.099379685
• Heavy Atom Count: 13
• Complexity: 133

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1CCOC(OC1)C2=CC=CC=C2

Technology Process of 1,3-Dioxepane, 2-phenyl-

There total 6 articles about 1,3-Dioxepane, 2-phenyl- 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: 95.0%

Butane-1,4-diol (110-63-4) + benzaldehyde (100-52-7) → 2-phenyl-[1,3]dioxepane (2749-68-0)

Guidance literature:

With phosphorus modified SO₄^(2-)/TiO₂; In cyclohexane; for 2h; Dean-Stark; Reflux;

DOI:10.4067/s0717-97072015000300006

Reference yield: 67.0%

2-phenyl-4,7-dihydro-1,3-dioxepine (2568-24-3) → 2-phenyl-4,5-dihydro-[1,3]dioxepine (35174-10-8) + 2-phenyl-[1,3]dioxepane (2749-68-0)

Guidance literature:

With sodium tetrahydroborate; tris(triphenylphosphine)ruthenium(II) chloride; In methanol; at 70 ℃; for 3h; Inert atmosphere;

DOI:10.1021/acs.joc.0c00390

Reference yield:

(bis(allyloxy)methyl)benzene (56318-28-6) → 2-phenyl-4,5-dihydro-[1,3]dioxepine (35174-10-8) + 2-phenyl-[1,3]dioxepane (2749-68-0)

Guidance literature:

Multi-step reaction with 2 steps

1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 2 h / Inert atmosphere; Reflux

2: tris(triphenylphosphine)ruthenium(II) chloride; sodium tetrahydroborate / methanol / 3 h / 70 °C / Inert atmosphere

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; sodium tetrahydroborate; tris(triphenylphosphine)ruthenium(II) chloride; In methanol; dichloromethane;

DOI:10.1021/acs.joc.0c00390

upstream raw materials:

Butane-1,4-diol

benzaldehyde dimethyl acetal

benzaldehyde

2-phenyl-4,7-dihydro-1,3-dioxepine

Downstream raw materials:

4-benzoyloxybutan-1-ol

4-oxobutyl benzoate

benzoicacid 4-bromo-butyl ester

diethyl [1,1-2H₂]-4-benzyloxybutyl-N-t-butoxycarbonylaminomalonate

Refernces

• 1、 Ghosh, Arun K.,Belcher, Miranda R.. "Lewis Acid-Catalyzed Vinyl Acetal Rearrangement of 4,5-Dihydro-1,3-dioxepines: Stereoselective Synthesis of cis- And trans-2,3-Disubstituted Tetrahydrofurans". . p. 10399 - 10412. Retrieved 2020/09/02.
• 2、 Jin, Yan,Shi, Jing,Zhang, Fumin,Zhong, Yijun,Zhu, Weidong. "Synthesis of sulfonic acid-functionalized MIL-101 for acetalization of aldehydes with diols". . p. 167 - 171. Retrieved 2014/01/17.