1-Undecyne

Base Information

• Chemical Name: 1-Undecyne
• CAS No.: 2243-98-3
• Molecular Formula: C11H20
• Molecular Weight: 152.28
• Hs Code.: 2901299090
• European Community (EC) Number: 218-825-1
• NSC Number: 87633
• UNII: Y07U3Q24US
• DSSTox Substance ID: DTXSID8062288
• Nikkaji Number: J125.121J
• Wikidata: Q27159718
• Mol file: 2243-98-3.mol

Synonyms:1-Undecyne;2243-98-3;undec-1-yne;undecyne;102681-76-5;UNII-Y07U3Q24US;Y07U3Q24US;EINECS 218-825-1;NSC 87633;NSC-87633;1-C11H20;Rutylidene;NSC87633;1-Undecyne, AldrichCPR;NCIOpen2_001194;DTXSID8062288;CHEBI:87545;CAA24398;C11H20;MFCD00015063;AKOS006230421;AS-56253;CS-0206842;FT-0608328;U0033;D92754;EN300-124916;Q27159718

Chemical Property of 1-Undecyne

Chemical Property:

• Vapor Pressure: 0.605mmHg at 25°C
• Melting Point: -25°C
• Refractive Index: 1.4300
• Boiling Point: 73°C 10mm
• Flash Point: 65.2°C
• PSA: 0.00000
• Density: 0.785g/cm³
• LogP: 3.76030
• Storage Temp.: Refrigerator
• Solubility.: Chloroform, Methanol (Sparingly)
• Water Solubility.: Miscible with acetone, ether, ethanol and benzene. Slightly miscible with water.
• XLogP3: 5.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 7
• Exact Mass: 152.156500638
• Heavy Atom Count: 11
• Complexity: 105

Purity/Quality:

98%,99%, ^*data from raw suppliers

1-Undecyne ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 10-53-36
• Safety Statements: 24/25-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCC#C
• Uses: 1-Undecyne is a reagent used in organic chemical synthesis. Used in the synthesis of antimalarial and antitrypanosomal agents.

Technology Process of 1-Undecyne

There total 50 articles about 1-Undecyne 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: 89.0%

(Z)-1-bromoundec-1-ene (66142-59-4) → 1-undecyne (2243-98-3)

Guidance literature:

With tetrabutyl ammonium fluoride; In N,N-dimethyl-formamide; at 60 ℃; for 2h;

DOI:10.1021/jo802101a

Reference yield: 88.0%

Methyl decanoate (110-42-9) + dimethyl 1-(1-diazo-2-oxopropyl)phosphonate (90965-06-3) → 1-undecyne (2243-98-3)

Guidance literature:

Methyl decanoate; With diisobutylaluminium hydride; In n-heptane; dichloromethane; at -78 ℃;

dimethyl 1-(1-diazo-2-oxopropyl)phosphonate; With potassium carbonate; In methanol; n-heptane; dichloromethane; at 20 ℃; Further stages.;

DOI:10.1016/j.tetlet.2004.05.139

Reference yield: 82.0%

1-(benzotriazol-1-yl)-2-undecanone p-tosylhydrazone (189343-58-6) → 1-undecyne (2243-98-3)

Guidance literature:

With n-butyllithium; In diethyl ether; 1) -78 deg C, 0.5 h; 2) rt, 48 h;

DOI:10.1021/jo962291t

upstream raw materials:

2,2-dichloro-undecane

1-Bromononane

sodium acetylide

1-iodononane

Downstream raw materials:

1-chloro-7-heptadecyne

(E)-2-iodo-1-tosyl-1-undecene

methyl nonyl ketone

(Z)-1-tosyl-1-undecene

Refernces

Total synthesis of dendrobate alkaloid (+)-241D, isosolenopsin and isosolenopsin a: Application of a gold-catalyzed cyclization

10.1039/c2ob25685a

The research focuses on the total synthesis of piperidine alkaloids, specifically (+)-241D, isosolenopsin, and isosolenopsin A, which are derived from D-alanine. The study employs a gold-catalyzed cyclization as the key step to access the chiral pyridinone intermediates, which are crucial for the synthesis of these alkaloids. The synthesis involves multiple steps, including the preparation of chiral synthons, gold-catalyzed intramolecular cyclization, and stereoselective reductions. The experiments utilized various reactants such as N-Boc-D-alanine, undecyne, BuLi, PPh3AuCl, and AgSbF6, among others, and employed techniques like Arndt–Eistert homologation and catalytic hydrogenation. The synthesized compounds were analyzed using spectroscopic methods (1H and 13C NMR, IR, and HRMS) and optical rotation measurements to confirm their structures and enantiomeric purity.