{[(Pent-3-yn-1-yl)oxy]methyl}benzene

Base Information

• Chemical Name: {[(Pent-3-yn-1-yl)oxy]methyl}benzene
• CAS No.: 98689-60-2
• Molecular Formula: C12H14O
• Molecular Weight: 174.243
• DSSTox Substance ID: DTXSID80542574
• Nikkaji Number: J1.510.560G
• Wikidata: Q82419288
• Mol file: 98689-60-2.mol

Synonyms:98689-60-2;{[(Pent-3-yn-1-yl)oxy]methyl}benzene;DTXSID80542574

Chemical Property of {[(Pent-3-yn-1-yl)oxy]methyl}benzene

Chemical Property:

• PSA: 9.23000
• LogP: 2.61660
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 174.104465066
• Heavy Atom Count: 13
• Complexity: 178

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC#CCCOCC1=CC=CC=C1

Technology Process of {[(Pent-3-yn-1-yl)oxy]methyl}benzene

There total 2 articles about {[(Pent-3-yn-1-yl)oxy]methyl}benzene 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: 99.0%

pent-3-yn-1-ol (10229-10-4) + benzyl bromide (100-39-0) → 5-benzyloxypent-2-yne (98689-60-2)

Guidance literature:

pent-3-yn-1-ol; With 1H-imidazole; sodium hydride; In tetrahydrofuran; at 0 ℃; for 0.5h;

benzyl bromide; With tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; at 0 - 24 ℃;

DOI:10.1021/ol800341z

Reference yield:

5-benzyloxy-1-pentyne (57618-47-0) → 5-benzyloxypent-2-yne (98689-60-2) + 5-(benzyloxy)pentan-2-one (13329-18-5) + 5-benzyloxypenta-1,2-diene (203577-52-0)

Guidance literature:

With C₄₁H₅₃AuClF₃NOP; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate; at 60 ℃; for 8h;

DOI:10.1021/ja503909c

Reference yield: 100.0%

5-benzyloxypent-2-yne (98689-60-2) + allylmagnesium bromide (1730-25-2) → ((E)-4-Methyl-hepta-3,6-dienyloxymethyl)-benzene

Guidance literature:

With iron(III)-acetylacetonate; In toluene; at 20 ℃; for 7h;

DOI:10.1002/1521-3773(20010202)40:3<621::AID-ANIE621>3.0.CO;2-O

upstream raw materials:

pent-3-yn-1-ol

benzyl bromide

5-benzyloxy-1-pentyne

Downstream raw materials:

(E)-5-benzyloxy-2-dimethylphenylsilyl-2-pentene

(E)-5-benzyloxy-3-dimethylphenylsilyl-2-pentene

2,3-bis(dimethylphenylsilyl)-5-benzyloxy-2-pentene

5-benzyloxy-2-(dimethylphenylsilyl)-2-pentene

Refernces

• 1、 Wang, Zhixun,Wang, Yanzhao,Zhang, Liming. "Soft propargylic deprotonation: Designed ligand enables au-catalyzed isomerization of alkynes to 1,3-Dienes". supporting information. p. 8887 - 8890. Retrieved 2014/07/08.
• 2、 Ilardi, Elizabeth A.,Stivala, Craig E.,Zakarian, Armen. "Hexafluoroisopropanol as a unique solvent for stereoselective lododesilylation of vinylsilanes". supporting information; experimental part. p. 1727 - 1730. Retrieved 2009/04/10.