Norcapillene

Base Information

• Chemical Name: Norcapillene
• CAS No.: 4009-22-7
• Molecular Formula: C11H8
• Molecular Weight: 140.185
• Hs Code.: 2902909090
• DSSTox Substance ID: DTXSID00450687
• Nikkaji Number: J798.439A
• Wikidata: Q27155282
• Mol file: 4009-22-7.mol

Synonyms:1,3-pentadiynylbenzene;Norcapillene;4009-22-7;1-Phenyl-1,3-pentadiyne;penta-1,3-diynyl-benzene;(Penta-1,3-diyn-1-yl)benzene;CHEBI:81344;DTXSID00450687;C17796;Q27155282

Chemical Property of Norcapillene

Chemical Property:

• PSA: 0.00000
• LogP: 2.06140
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 2
• Exact Mass: 140.062600255
• Heavy Atom Count: 11
• Complexity: 228

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC#CC#CC1=CC=CC=C1

Technology Process of Norcapillene

There total 22 articles about Norcapillene 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%

(E)-1-[(1-chloro-2-methyl-4-phenylbut-1-en-3-yn-1-yl)sulfinyl]-4-methylbenzene (1303963-73-6) → agropyrene (4009-22-7)

Guidance literature:

With isopropylmagnesium chloride; In diethyl ether; toluene; at -78 - 0 ℃; for 2h;

DOI:10.3762/bjoc.17.94

Reference yield: 92.0%

(E)-1-(4-chlorobut-3-en-1-ynyl)benzene (18685-03-5) + methyl iodide (74-88-4) → agropyrene (4009-22-7)

Guidance literature:

(E)-1-(4-chlorobut-3-en-1-ynyl)benzene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

methyl iodide; In tetrahydrofuran; hexane; at -78 - 20 ℃;

DOI:10.1021/ol0623825

Reference yield: 85.0%

Trifluoro-methanesulfonic acid (Z)-1-phenylethynyl-propenyl ester (101160-52-5) → agropyrene (4009-22-7)

Guidance literature:

With potassium 2,6-di-tert-butylphenolate; In 1,2-dimethoxyethane; at 50 - 55 ℃; for 0.5h;

DOI:10.1055/s-1985-31403

upstream raw materials:

1-phenylpenta-1,3-diene

(penta-1,4-diynyl)benzene

diiodomethane

buta-1,3-diynylbenzene

Downstream raw materials:

1,4-diphenyl-1,3-butadiyne

2,4-hexadiyne

2-methyl-1,5-diphenyl-1H-phosphole 1-sulfide

1-isopropyl-2-methyl-5-phenyl-1H-phosphole 1-sulfide

Refernces

• 1、 Ando, Akane,Imafuji, Aki,Kimura, Tsutomu,Sekiguchi, Koto. "Fritsch-Buttenberg-Wiechell rearrangement of magnesium alkylidene carbenoids leading to the formation of alkynes". . p. 1352 - 1359. Retrieved 2021/06/06.
• 2、 Lysenko, Sergej,Volbeda, Jeroen,Jones, Peter G.,Tamm, Matthias. "Catalytic metathesis of conjugated diynes". supporting information; experimental part. p. 6757 - 6761. Retrieved 2012/08/13.