76691-55-9

Upstream product

• 112-38-9 10-undecenoic acid 
• 100-46-9 benzylamine 
• 38460-95-6 undec-10-enoyl chloride 
• 134781-64-9 Mesitylenesulfonic 10-undecenoic anhydride 
• 134781-62-7 2,4,6-Trichlorobenzoic 10-undecenoic anhydride 
• 134781-63-8 S-pyridin-2-yl 10-undecenethioate 

Downstream Products

• 53179-04-7 undec-10-enenitrile 
• 76691-75-3 N-benzylundec-10-en-1-amine 

Relevant academic research and scientific papers

Ammonia-borane as a Catalyst for the Direct Amidation of Carboxylic Acids

Ammonia-borane serves as an efficient substoichiometric (10%) precatalyst for the direct amidation of both aromatic and aliphatic carboxylic acids. In situ generation of amine-boranes precedes the amidation and, unlike the amidation with stoichiometric amine-boranes, this process is facile with 1 equiv of the acid. This methodology has high functional group tolerance and chromatography-free purification but is not amenable for esterification. The latter feature has been exploited to prepare hydroxyl- and thiol-containing amides.

A General and Selective Rhodium-Catalyzed Reduction of Amides, N-Acyl Amino Esters, and Dipeptides Using Phenylsilane

This article describes a selective reduction of functionalized amides, including N-acyl amino esters and dipeptides, to the corresponding amines using simple [Rh(acac)(cod)]. The catalyst shows excellent chemoselectivity in the presence of different sensitive functional moieties. A selective reduction of functionalized amides, including N-acyl amino esters and dipeptides, to the corresponding amines using simple [Rh(acac)(cod)] is described (see scheme). The catalyst shows excellent chemoselectivity in the presence of different sensitive functional moieties. Even the selective reduction of a secondary amide bond in the presence of a ketone is possible.

Metallic magnesium: an efficient catalyst toward N-aryl and N-alkyl substituted amides directly from aliphatic carboxylic acids

Abstract An efficient and inexpensive procedure for direct conversion of aliphatic carboxylic acids into amides has been developed using anilines or aliphatic amines and Mg(0) as catalyst in toluene. The amides were obtained by single crystallization in moderate to excellent yields with high purity. Graphical Abstract: [Figure not available: see fulltext.]

The thermal amidation of carboxylic acids revisited

Factors affecting the thermal condensation of carboxylic acids with amines have been investigated, and an effective protocol for this waste-minimized, environmentally benign transformation has been identified. Fourteen examples demonstrate the applicability of this procedure to aliphatic, aromatic and heteroaromatic carboxylic acids and primary and secondary aliphatic as well as aromatic amines. The approach leads to the corresponding amides in good yields. Georg Thieme Verlag Stuttgart.

Synthesis of medium and large cyclic amines in rhodium-catalysed reactions of aminoalkenes with H2/CO1

Rhodium-catalysed reactions of N-benzyl- or N-alkyl-aminoalkenes (6) with H2/CO can give cyclic amines (7) (7-13 ring size) in good to excellent yields when BIPHEPHOS is used as a ligand. Hydrogenation of the aminoalkene becomes a competing reaction for the smaller rings but can be overcome by using a H2/CO gas ratio of 1:5. Reactions of 2-alkenyloxybenzylamines (13) gave 9-, 12- and 17-membered rings (14) in 30-40% yield, but dimer formation (16) and/or hydrogenation were competing reactions. Similar reactions of alkenylamides and ortho-alkenylanilines gave only non-cyclized amino aldehydes as products in low isolated yields.

Cyclization of 9-Substituted Decanoic Acid Derivatives to 9-Decanolide and 9-Decanelactam

Several standard and some novel cyclization reactions have been applied to 9-substituted decanoic acids to establish which are the optimum procedures for lactonization and lactamization at 80 deg C under identical high-dilution conditions.The methods of Galli-Mandolini and Kellogg (cyclization of 9-bromodecanoate ion), Gerlach (cyclization of S-2-pyridyl 9-hydroxydecanethioate in the presence of AgClO4), and Yamaguchi (activation of the carboxyl group as a mixed anhydride) in the presence of an excess of DMAP appear to be the most useful for the preparation of the 10-membered lactone, phoracantolide I, under these conditions.Analogously, treatment of S-2-pyridyl 9-azidodecanethionate with Sn(SePh)3(1-) afforded the best yield of the 10-membered lactam.The mixed anhydrides RCOOCOAr (Ar = 2,4,6-trichlorophenyl) are more reactive than thioesters RCOSPy (Py = 2-pyridyl) with benzyl alcohol or benzylamine; it is confirmed that the addition of DMAP activates the reaction of alcohols with mixed anhydrides much more than with pyridyl thioesters, while the addition of Ag(1+) strongly activates RCOSPy in relation to either RCOOCOAr or RCOOSO2Mes.

Insect Juvenile Hormone Analogues: Part VII - Synthesis of Long Chain Aromatic Ethers & Nitrogen Analogues

Syntheses of various aromatic ethers of undecenyl bromide and thio ethers of undecenyl and undecanyl bromides with 2-benzothiazolethiol are described.The preparation of a few amides and their corresponding amines from undecenoic acid and different aromatic amines and benzyl amine are also reported.The bromo derivatives of a few amides have also been prepared.These compounds have been tested on common Indian red cotton bug for their juvenile hormone activity.