27694-89-9

Basic information

• Product Name: undeca-1,2-dienylbenzene
• Synonyms: undeca-1,2-dienylbenzene
• CAS NO: 27694-89-9
• Molecular Weight: 228.378
• Mol File: 27694-89-9.mol

Chemical Properties

• CAS DataBase Reference: undeca-1,2-dienylbenzene(CAS DataBase Reference)
• NIST Chemistry Reference: undeca-1,2-dienylbenzene(27694-89-9)
• EPA Substance Registry System: undeca-1,2-dienylbenzene(27694-89-9)

Safety Data

• Hazardous Substances Data: 27694-89-9(Hazardous Substances Data)

Upstream product

• 17049-49-9 octylmagnesium bromide 
• 122044-10-4 Methanesulfinic acid (R)-1-phenyl-prop-2-ynyl ester 
• 764-93-2 1-decyne 
• 100-44-7 benzyl chloride 
• 100-52-7 benzaldehyde 
• 1497483-71-2 N,N-diethyl-1-phenylundec-2-yn-1-amine 
• 1497483-72-3 N,N-dibenzyl-1-phenylundec-2-yn-1-amine 
• 1497483-70-1 (3S)-methyl 2-(1-phenylundec-2-yn-1-yl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate 
• 1376191-20-6 C₂₇H₃₅N 
• 1376191-10-4 C₃₃H₃₉N 
• 22348-32-9 (S)-diphenylprolinol 
• 1376191-72-8 (2S)-1-((1S)-1-phenyl-2-undecyn-1-yl)-α,α-diphenylprolinol 
• 51207-65-9 N,N-diethyl-N-(((S)-pyrrolidin-2-yl)methyl)amine 
• 65921-41-7 (S)-2-(1-piperidinylmethyl)pyrrolidine 

Downstream Products

• 1409940-91-5 2-benzhydryl-1-octyl-1H-indene 

Relevant articles and documents

Room Temperature Allenation of Terminal Alkynes with Aldehydes

A gold-catalyzed room temperature allenation of terminal alkynes (ATA) with aldehydes affording 1,3-disubstituted allenes with diverse functional groups has been developed by identifying a gold(I) catalyst and an amine. The practicality of this reaction has been demonstrated by a ten gram-scale synthesis and the synthetic potentials have been demonstrated via various transformations and formal total synthesis of (?)-centrolobine. Mechanistic studies revealed that the gold catalyst, the aldehyde effect, the fluoroalkyl hydroxyl solvent (TFE or HFIP) and the structure of amine are vital in this room temperature ATA reaction.

A new gold-catalysed azidation of allenes

A new gold-catalysed azidation reaction of allenes is presented as a new highly modular approach for the synthesis of substituted allyl derivatives containing nitrogen from simple precursors. This journal is The Royal Society of Chemistry.

Zinc salt promoted diastereoselective synthesis of chiral propargylamines using chiral piperazines and their enantioselective conversion into chiral allenes

Zinc chloride catalyzed reactions of chiral piperazine derivatives 4a-d with 1-alkynes and aldehydes give chiral propargylamines in 67-95 % yields with up to 99:1 dr. The chiral propargylamines are converted into chiral allenes by using zinc bromide in sh

Mild-condition synthesis of allenes from alkynes and aldehydes mediated by tetrahydroisoquinoline (THIQ)

A practical 1,2,3,4-tetrahydroisoquinoline (THIQ)-mediated synthesis of 1,3-disubstituted allenes from terminal alkynes and aldehydes under mild conditions in the presence of CuBr first and then ZnI2 was reported. This telescoped allene synthes

Enantioselective synthesis of both enantiomers of chiral allenes using chiral N-methylcamphanyl piperazine templates

The reaction of unsubstitued camphanyl-piperazine 4 with ZnCl2, phenylacetylene, and benzaldehyde in toluene gave the corresponding dipropargylamine (i.e., 15) with opposite configurations at the newly formed stereogenic centres, which, upon re

Studies on ZnBr2-mediated synthesis of axially chiral aryl-substituted allenes from terminal alkynes, aromatic aldehydes and (S)-α,α-diphenylprolinol

The studies on the ZnBr2-mediated synthesis of axially chiral aryl-substituted allenes from terminal alkynes, aromatic aldehydes, and commercially available chiral amine (S)-α,α-diphenylprolinol were conducted. Axially chiral aryl-substituted a

Bimetallic enantioselective approach to axially chiral allenes

An efficient bimetallic Zn(II)/Cu(I)-mediated asymmetric synthesis of simple axially chiral allenes from terminal alkynes and aldehydes was realized by taking advantage of the chiral amine (S)-α,α-diphenylprolinol 3. This one-pot procedure is compatible w

Copper(I) halide promoted diastereoselective synthesis of chiral propargylamines and chiral allenes using 2-dialkylaminomethylpyrrolidine, aldehydes, and 1-alkynes

Copper bromide promoted reactions of aldehydes, 1-alkynes, and chiral 2-dialkylaminomethylpyrrolidine at 25 C give the corresponding chiral propargylamine derivatives in up to 96% yield and 99:1 dr that are readily converted to the corresponding disubstit

Highly enantioselective synthesis of chiral allenes by sequential creation of stereogenic center and chirality transfer in a single pot operation

Chiral allenes are readily accessed in a single pot operation in the reaction of terminal alkynes, aldehydes, chiral secondary amines, and zinc halides in good yields (up to 77% yield) and excellent enantioselectivities (up to 99% ee) in toluene at 120 °C. The reaction proceeds through initial formation of chiral propargylamine intermediates with creation of a new stereogenic center and subsequent chirality transfer via an intramolecular hydride shift to produce chiral allenes with high enantiomeric purities.

One-pot synthesis of 1,3-disubstituted allenes from 1-alkynes, aldehydes, and morpholine

(Formula Presented) ZnI2 has been identified as the catalyst for the one-step synthesis of allenes from terminal alkynes and aldehydes with morpholine as the base in toluene. The reaction is believed to proceed via the intermediacy of propargylic amines, which was converted to allenes by a sequential hydride transfer and β-elimination process. The reaction is applicable for both aromatic and aliphatic aldehydes. Functionalities such as halide, hydroxyl, or amine may be tolerated. Copyright