21676-08-4

Basic information

• Product Name: 4-Undecen-1-ol, (E)-
• Synonyms: 4-Undecen-1-ol, (E)-;(E)-4-Undecen-1-ol;trans-4-Undecen-1-ol
• CAS NO: 21676-08-4
• Molecular Formula: C₁₁H₂₂O
• Molecular Weight: 170
• Mol File: 21676-08-4.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 255℃
• Flash Point: 96℃
• Appearance: /
• Density: 0.846
• PKA: 15.09±0.10(Predicted)
• CAS DataBase Reference: 4-Undecen-1-ol, (E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Undecen-1-ol, (E)-(21676-08-4)
• EPA Substance Registry System: 4-Undecen-1-ol, (E)-(21676-08-4)

Safety Data

• Hazardous Substances Data: 21676-08-4(Hazardous Substances Data)

Upstream product

• 6564-95-0 4-oxobutyl acetate 
• 104410-92-6 1-Methyl-2-trimethylsilanylmethyl-1,2,3,6-tetrahydro-pyridine 
• 109-06-8 α-picoline 
• 111-25-1 1-bromo-hexane 
• 5631-95-8 2,3-dichlorotetrahydro-2H-pyran 
• 35329-56-7 methyl (E)-undec-4-enoate 
• 54377-35-4 undec-4-yn-1-ol 
• 55976-13-1 (E)-undeca-1,4-diene 
• 6393-56-2 pentylmagnesium chloride 
• 104410-96-0 Trimethyl-[(Z)-6-(tetrahydro-pyran-2-yloxy)-hex-2-enyl]-ammonium; iodide 
• 104410-95-9 ((Z)-6-Hydroxy-hex-2-enyl)-trimethyl-ammonium; iodide 
• 104410-97-1 (Z)-6-Chloro-hex-4-en-1-ol 
• 3761-92-0 n-hexylmagnesium bromide 
• 72081-15-3 6-lithio-3,4-dihydro-2H-pyran 

Downstream Products

• 68820-35-9 (E)-undec-4-enal 
• 940-53-4 2-hexylpiperidine 
• 35507-72-3 (E)-1,8-pentadecadiene 

Relevant articles and documents

CP2TiCl2-catalyzed hydroalumination of internal alkynes: An access to (Z)-olefins

The reduction of alkynols with LiAlH4 in diglyme is a long known process leading to the formation of (E)-alkenols. We have, by serendipity, found that, in the presence of a catalytic amount (10%) of Cp2TiCl2, the stereoselectivity of the reaction is reversed, leading to the selective formation of the (Z)-alkenols. The scope and limitations of this methodology and a postulated catalytic cycle are also discussed.

Azidomercurations of alkenes: Mercury-promoted Schmidt reactions

Azides bearing a suitably disposed alkene, when treated with either mercuric perchlorate or mercuric trifluoromethanesulfonate, produce bicyclic iminium ions. This new version of the Schmidt reaction proceeds by capture of the mercuronium ion intermediate by the azide to produce an aminodiazonium ion, which suffers a 1,2-shift to give an iminium ion (e.g., 10 → 16 → 17 → 18). Reduction of the iminium ion may then be carried out to produce an amine. Compared to earlier work on the protic acid-promoted intramolecular Schmidt reaction of azido-alkenes, the mercury-promoted Schmidt reaction has several advantages. First, the acid-promoted Schmidt reaction of azido-alkenes requires that the intermediate carbocations be tertiary, allylic, benzylic, or propargylic. The mercury-promoted method has no such limitation; thus even 1,2-disubstituted alkenes may be used. Second, the mercury-promoted method is milder, allowing the presence of acid-sensitive functionality. The protic version, typically employing trifluoromethanesulfonic acid, is limited in its functional group tolerance. Third, whereas carbocation rearrangement is often observed prior to cyclization/rearrangement in the acid-promoted Schmidt reaction, the mercury-promoted method avoids this problem. Fourth, the presence of the mercurio group during the rearrangment may alter the regioselectivity of the 1,2-migration. Finally, the mercury-bearing iminium ions that are the result of the Schmidt reaction were found to be sensitive to protodemercuration, precluding their use in other transformations.

Synthesis of 7,11-dienes from enol ether and Grignard reagents under nickel catalysis: sex pheromones of Drosophila melanogaster

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