1,4,7,10,13,16,19-Heptaoxacyclohenicosane

Base Information

• Chemical Name: 1,4,7,10,13,16,19-Heptaoxacyclohenicosane
• CAS No.: 33089-36-0
• Molecular Formula: C14H28 O7
• Molecular Weight: 308.372
• European Community (EC) Number: 251-373-3
• UNII: GF978SJ9Z2
• DSSTox Substance ID: DTXSID50186747
• Nikkaji Number: J319.499J
• Wikipedia: 21-Crown-7
• Wikidata: Q55176433
• Mol file: 33089-36-0.mol

Synonyms:21-Crown-7;1,4,7,10,13,16,19-Heptaoxacyclohenicosane;33089-36-0;[21]Crown-7-ether;CCRIS 3602;EINECS 251-373-3;GF978SJ9Z2;UNII-GF978SJ9Z2;SCHEMBL3137753;DTXSID50186747;AC9243;MFCD00054526;C14-H28-O7;AS-82775;SY250768;LS-188567;Q55176433

Chemical Property of 1,4,7,10,13,16,19-Heptaoxacyclohenicosane

Chemical Property:

• Vapor Pressure: 8.09E-08mmHg at 25°C
• Boiling Point: 448.6°Cat760mmHg
• Flash Point: 184.7°C
• PSA: 64.61000
• Density: 0.995g/cm³
• LogP: 0.11620
• XLogP3: -0.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 0
• Exact Mass: 308.18350323
• Heavy Atom Count: 21
• Complexity: 131

Purity/Quality:

97% ^*data from raw suppliers

21-CROWN-7 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1COCCOCCOCCOCCOCCOCCO1

Technology Process of 1,4,7,10,13,16,19-Heptaoxacyclohenicosane

There total 30 articles about 1,4,7,10,13,16,19-Heptaoxacyclohenicosane 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: 68.0%

Tetraethylene glycol (112-60-7) + 1,2-bis(2-chloroethoxy)ethane (112-26-5,27252-69-3) → 1,4,7,10,13,16,10-heptaoxacyclohenicosane (33089-36-0)

Guidance literature:

With potassium hydroxide; for 0.166667h; microwave irradiation;

DOI:10.1080/10426500500271972

Reference yield: 59.0%

heptaethylene glycol (5617-32-3) → 1,4,7,10,13,16,10-heptaoxacyclohenicosane (33089-36-0)

Guidance literature:

With potassium hydroxide; p-toluenesulfonyl chloride; In 1,4-dioxane; at 50 ℃;

DOI:10.1246/bcsj.53.1689

Reference yield: 54.0%

tetraethylene glycol di(p-toluenesulfonate) (37860-51-8) + 2,2'-[1,2-ethanediylbis(oxy)]bisethanol (112-27-6) → 1,4,7,10,13,16,10-heptaoxacyclohenicosane (33089-36-0)

Guidance literature:

With aluminum oxide; potassium fluoride; In acetonitrile; for 72h; Ambient temperature;

DOI:10.1246/cl.1980.533

upstream raw materials:

18-crown-6 ether

heptaethylene glycol

Tetraethylene glycol

triethylene glycol di-(p-toluenesulfonate)

Downstream raw materials:

18-crown-6 ether

4-(1,4,7,10,13,16,19-Heptaoxa-cyclohenicos-2-yl)-2-methyl-quinoline

kryptofix 221

[2.2.2]cryptande

Refernces

Enantioselective total synthesis of heliespirone B

10.1016/j.tetlet.2011.12.115

The research describes the first enantiocontrolled total synthesis of heliespirone B, a natural product with allelopathic activity that has potential for becoming a lead compound for new types of agrochemicals. The purpose of this study was to develop an efficient and enantioselective synthetic route for heliespirone B, which has a challenging 1-oxaspiro[5.5]undecenone skeleton with four stereogenic centers. The key steps in the synthesis included a biomimetic intramolecular oxy-Michael reaction to construct the six-membered oxaspirocyclic core structure and a highly regio- and diastereoselective reduction of the carbonyl group at C2. The researchers used a variety of reagents and conditions, including 21-Crown-7 as additive used in the intramolecular oxy-Michael reaction and Zn(BH4)2 for the selective reduction of the carbonyl group. The synthesis was achieved with a longest linear sequence of 10 steps and an overall yield of 23%. The study concluded that the developed synthetic route is general and efficient, and it could be applied to the synthesis of other related natural products.