28897-20-3

Basic information

• Product Name: 6,10-dimethylundeca-1,5,9-trien-4-ol
• Synonyms: 6,10-dimethylundeca-1,5,9-trien-4-ol;6,10-Dimethyl-1,5,9-undecatrien-4-ol
• CAS NO: 28897-20-3
• Molecular Formula: C₁₃H₂₂O
• Molecular Weight: 194.31318
• EINECS: 249-293-9
• Mol File: 28897-20-3.mol

Chemical Properties

• Boiling Point: 284.2°Cat760mmHg
• Flash Point: 104.8°C
• Appearance: /
• Density: 0.871g/cm³
• Vapor Pressure: 0.000348mmHg at 25°C
• Refractive Index: 1.479
• CAS DataBase Reference: 6,10-dimethylundeca-1,5,9-trien-4-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 6,10-dimethylundeca-1,5,9-trien-4-ol(28897-20-3)
• EPA Substance Registry System: 6,10-dimethylundeca-1,5,9-trien-4-ol(28897-20-3)

Safety Data

• Hazardous Substances Data: 28897-20-3(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron Letters, 28, p. 3707, 1987 DOI: 10.1016/S0040-4039(00)96362-7

InChI:InChI=1/C13H22O/c1-5-7-13(14)10-12(4)9-6-8-11(2)3/h5,8,10,13-14H,1,6-7,9H2,2-4H3/b12-10+

Upstream product

• 2622-05-1 allylmagnesium bromide 
• 5392-40-5 (E/Z)-3,7-dimethyl-2,6-octadienal 
• 591-87-7 Allyl acetate 
• 132017-23-3 C₁₅H₃₂BrSb 
• 556-56-9 allyl iodid 
• 688-61-9 Triallylborane 
• 106-95-6 allyl bromide 

Relevant articles and documents

Water-Compatible Synthesis of 2-Trifluoromethyl-1,3-Dioxanes

A water-compatible method for the diastereoselective synthesis of 2-trifluormethyl-1,3-dioxanes is described. The reaction proceeds under mild reaction conditions using simple inorganic bases; it has a very good substrate scope and can be performed with different Michael acceptors. Additionally, the reaction products can be further functionalized, showing an excellent perspective for future applications.

PROCESS FOR PREPARING ALPHA-DAMASCONE

The present invention relates to a process for preparing 1-(2,6,6-trimethylcyclohex-2- en-1-yl)but-2-en-1-one, which comprises a) providing 6,10-dimethylundeca-1,5,9-trien-4-ol, b) oxidizing 6,10-dimethylundeca-1,5,9-trien-4-ol provided in step a) with an oxidizing agent in the presence of at least one organic nitroxyl radical, at least one nitrate compound and an inorganic solid to yield 6,10-dimethylundeca-1,5,9- trien-4-one, c) reacting the 6,10-dimethylundeca-1,5,9-trien-4-one obtained in step b) with an acid to yield 1-(2,6,6-trimethylcyclohex-2-en-1-yl)but-2-en-1-one.

Barbier allylation of aldehydes and ketones with aluminium and catalytic indium metal: An economical alternative

An economical preparative protocol for the Barbier allylation of aldehydes and ketones in DMF, using aluminium foil in the presence of a catalytic amount of indium metal, is reported. All yields obtained are in general similar but slightly lower than those reported for the stoichiometric indium allylation. Aluminium alone failed to give rise to any detectable product. ARKAT-USA, Inc.

Ti-catalyzed Barbier-type allylations and related reactions

Titanocene(III) complexes, easily generated in situ from commercial Ti IV precursors, catalyze Barbiertype allylations, intramolecular crotylations (cyclizations), and prenylations of a wide range of aldehydes and ketones. The reaction displays surprising and unprecedented mechanistic subtleties. In cyclizations a fast and irreversible addition of an allyl radical to a TiIII-coordinated carbonyl group seems to occur. Intermolecular additions to conjugated aldehydes proceed through a coupling of a Ti IV-bound ketyl radical with an allyl radical. Reactions of ketones with allylic halides take place by the classical addition of an allylic organometallic reagent. The radical coupling processes enable transformations such as the highly regioselective α-prenylation that are otherwise difficult to achieve. The mild reaction conditions and the possibility to employ titanocene complexes in only catalytic quantities are highly attractive features of our protocol. These unusual properties have been taken advantage of for the straightforward synthesis of the natural products rosiridol, shikalkin, and 12-hydroxysqualene.

Granular indium Barbier allylation of carbonyl compounds: A more economical protocol

A new protocol, amenable to be used in large-scale preparations, using a cheaper form of indium metal and mild warming is reported for the Barbier allylation of aldehydes and ketones with allyl bromide in N,N-dimethylformamide. Georg Thieme Verlag Stuttgart.

Pentaalkylstiboranes. 1. Synthesis of Homobenzylic Alcohols, Homoallylic Alcohols, Ethyl 5-Aryl-5-hydroxypent-2-enoates, and β-Hydroxypropionic Acid Derivatives via Pentaalkylstiboranes

Although pentaalkylstiboranes have long been known, their applications in organic synthesis have not been exploited.It has been found that quaternary stibonium salts (n-Bu3SbCH2E)+X- (E = Ph, CH=CH2, CH=CHCO2Et, CO2Et, CN; X = Br, I, BPh4) on treatment with RLi (R = n-Bu, t-Bu, Ph) afford pentaalkylstiboranes, n-Bu3Sb(R)CH2E, which react with aromatic aldehydes to give, after subsequent hydrolysis, homobenzylic alcohols, homoallylic alcohols, ethyl 5-aryl-5-hydroxypent-2-enoates, and β-aryl-β-hydroxypropionitriles, respectively, in good to excellent yields.The reaction is chemoselective for aldehydes.

A Barbier allylation and a Reformatsky reaction of carbonyl compounds mediated by indium(I) iodide

Indium(I) iodide was found to mediate in the Barbier allylation and in the Reformatsky reaction of aldehydes and ketones to give homoallylic alcohols and β-hydroxy esters, respectively, presumably via allylindium(III) diiodide.

Charge Reversal of Electrophilic ?-Allylpalladium Intermediates; Carbonyl Allylation by Allylic Acetates with PdCl2(PhCN)2-SnCl2

Carbonyl allylation by stable allylic acetates with Pd0-SnCl2 occurred regio-, chemo-, and diastereoselectively to afford the corresponding homoallylic alcohols.

BARBIER-GRIGNARD-TYPE ALLYLATION OF ALDEHYDES WITH METALLIC ANTIMONY

Metallic-antimony-induced allylation of aldehydes by allylic halides and phosphates gave high yields of the corresponding homoallylic alcohols, regioselectively. α,β-Unsaturated aldehydes afforded only 1,2-addition products.

AN EFFICIENT METHOD FOR THE PREPARATION OF HOMOALLYLIC ALCOHOL DERIVATIVES BY THE REACTION OF ALLYL IODIDE WITH CARBONYL COMPOUNDS IN THE PRESENCE OF STANNOUS HALIDE

Allyl iodide reacts in situ under mild conditions with stannous halide to form allyltin dihaloiodide, which in turn reacts with carbonyl compounds in an aprotic solvent to give the corresponding homoallylic alcohol derivatives in good yields.