4,4-Dimethyl-3,5,8-trioxabicyclo[5.1.0]octane

Base Information

• Chemical Name: 4,4-Dimethyl-3,5,8-trioxabicyclo[5.1.0]octane
• CAS No.: 57280-22-5
• Molecular Formula: C7H12O3
• Molecular Weight: 144.17
• Hs Code.: 2932999099
• European Community (EC) Number: 421-750-9,629-743-4
• DSSTox Substance ID: DTXSID10972789
• Nikkaji Number: J718.806D
• Mol file: 57280-22-5.mol

Synonyms:4,4-dimethyl-3,5,8-trioxabicyclo[5.1.0]octane;57280-22-5;4,4-Dimethyl-3,5,8-trioxabic-yclo[5,1,0]Octane;MFCD16621162;4,4-Dimethyl-3,5,8-trioxabicyclo(5.1.0)octane;EC 421-750-9;4,4-dimethyl-3,5,8-trioxabicyclo-[5.1.0]-octane;4,4-dimethyl-3,5,8-trioxabicyclo[5,1,0]octane;SCHEMBL1223255;AMY5474;DTXSID10972789;GEKNCWQQNMEIMS-UHFFFAOYSA-N;BCP17091;CS1776;AKOS016007973;SB40516;AC-26559;AS-19260;SY053244;CS-0043326;D5200;EN300-136272;4,4-dimethyl-3,5, 8-trioxabicyclo[5.1.0]octane;A1-01688;Z1255426054

Chemical Property of 4,4-Dimethyl-3,5,8-trioxabicyclo[5.1.0]octane

Chemical Property:

• Refractive Index: 1.4560 to 1.4600
• Boiling Point: 179℃
• Flash Point: 56℃
• PSA: 30.99000
• Density: 1.071
• LogP: 0.53670
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 144.078644241
• Heavy Atom Count: 10
• Complexity: 130

Purity/Quality:

98% ^*data from raw suppliers

4,4-Dimethyl-3,5,8-trioxabicyclo[5.1.0]octane ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36-43
• Safety Statements: 26-36/37-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OCC2C(O2)CO1)C
• Uses: 4,4-Dimethyl-3,5,8-trioxabicyclo[5.1.0]octane is used in the CO2-mediated formation of chiral carbamates from meso-epoxides via polycarbonate intermediates and amine nucleophiles, which opens up a wide a wide range of CO2-based carbamate scaffolds with excellent yields and 99% enantiomeric excess.

Technology Process of 4,4-Dimethyl-3,5,8-trioxabicyclo[5.1.0]octane

There total 6 articles about 4,4-Dimethyl-3,5,8-trioxabicyclo[5.1.0]octane 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: 88.0%

→ 4,4-dimethyl-3,5,8-trioxabicyclo[5.1.0]-octane (57280-22-5) + (5R,6S)-6-(benzylamino)-2,2-dimethyl-1,3-dioxepan-5-ol

Guidance literature:

Reference yield: 85.2%

2,2-dimethyl-4,7-dihydro-1,3-dioxepin (1003-83-4) → 4,4-dimethyl-3,5,8-trioxabicyclo[5.1.0]-octane (57280-22-5)

Guidance literature:

With disodium hydrogenphosphate; dihydrogen peroxide; sodium hydroxide; In methanol; water; acetonitrile; at 60 - 80 ℃; pH=7 - 9.5; Large scale; Green chemistry;

Reference yield: 68.0%

→ 4,4-dimethyl-3,5,8-trioxabicyclo[5.1.0]-octane (57280-22-5)

Guidance literature:

upstream raw materials:

2,2-dimethyl-4,7-dihydro-1,3-dioxepin

2,2-dimethoxy-propane

Downstream raw materials:

trans-6-benzylamino-2,2'-dimethyl-1,3-dioxocycloheptan-5-ol

(2R)-2-benzyloxycarbonylamino-2-[(4S)-2,2-dimethyl-1,3-dioxolane-4-yl]ethanol

Refernces

• 1、 -. "Method for efficiently preparing 4,4-dimethyl-3,5,8-trioxabicyclo[5,1,0]octane". Paragraph 0032-0033; 0035-0036; 0038-0039. . Retrieved 2018/11/27.
• 2、 Szpera, Robert,Kovalenko, Nadia,Natarajan, Kalaiselvi,Paillard, Nina,Linclau, Bruno. "The synthesis of the 2, 3-difluorobutan-1, 4-diol diastereomers". supporting information. p. 2883 - 2887. Retrieved 2018/01/17.