26560-14-5Relevant academic research and scientific papers
PROCESS FOR MAKING A CONJUGATED DIENE FROM AN ALLYL ALCOHOL
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Page/Page column 36, (2022/01/05)
An in-situ method for making a conjugated diene from an allyl alcohol comprising the conversion of the allyl alcohol to an allyl carbonate, allyl ester or allyl formate with concomitant or subsequent conversion of the allyl carbonate, allyl ester or allyl formate to the conjugated diene; the products obtained by said method, and the uses of said products.
Templating effects in aristolochene synthase catalysis: Elimination versus cyclisation
Faraldos, Juan A.,Gonzalez, Veronica,Senske, Michael,Allemann, Rudolf K.
supporting information; experimental part, p. 6920 - 6923 (2011/11/04)
Analysis of the products generated by mutants of aristolochene synthase from P. roqueforti (PR-AS) revealed the prominent structural role played by the aliphatic residue Leu 108 in maintaining the productive conformation of farnesyl diphosphate to ensure C1-C10 (σ-bond) ring-closure and hence (+)-aristolochene production.
Highly regio- and stereoselective synthesis of (Z)-trisubstituted alkenes via propyne bromoboration and tandem Pd-catalyzed cross-coupling
Wang, Chao,Tobrman, Tomas,Xu, Zhaoqing,Negishi, Ei-Ichi
supporting information; experimental part, p. 4092 - 4095 (2009/12/06)
Contrary to all previous reports, bromoboration of propyne with BBr 3 proceeds in ≥98% syn-selectivity to produce (Z)-2-bromo- 1propenyldibromoborane (1). Although 1 Is readily prone to stereoisomerization, It can be converted to the pinacolboronate (2) of ≥ 98% isomeric purity by treatment with pinacol. which may then be subjected to Negishi coupling to give tri substituted (2)-alkenylpinacolboronates (3) containing various R groups In 73-90% yields. Iodinolysis of 3 affords alkenyl iodides (4) In 80-90% yields. All alkenes isolated and identified are ≥98% Z.
Characterization of vinyl-substituted, carbon-carbon double bonds by GC/FT-IR analysis.
Svatos,Attygalle
, p. 1827 - 1836 (2007/10/03)
Vapor-phase infrared spectra allow the determination of the stereochemistry of carbon-carbon double bonds conjugated with a vinyl group. Cis and trans isomers of unsubstituted 1,3-alkadienes can be differentiated on the basis of the differences observed in the 900-1000 cm-1 region (spectra of cis isomers show two bands at 993 and 906 cm-1, while those of trans compounds show three absorptions at 998, 949, and 902 cm-1) and the 1590-1650 cm-1 region (the C=C stretch bands are observed at 1595 and 1642 cm-1 for cis compounds and at 1604 and 1650 cm-1 for trans compounds). Compounds bearing CH2=CHC(CH3)=CHCH2- and CH2=CHC(=CH2)-CH2- structural moieties, referred to as alpha- and beta-type compounds, are frequently encountered as natural products. For compounds bearing alpha-type groups, the cis/trans configuration of the trisubstituted double bond can be determined unambiguously. An absorption at 3095-3091 cm-1, for the =CH2 stretch vibration, is common to both of these groups; however, due to the presence of two =CH2 groups, the relative intensity of the band is much higher for beta-type compounds. For alpha-type compounds, a cis configuration at the C-3 carbon atom is characterized by a =CH2 wag absorption at 907-906 cm-1. For beta-type compounds and 3E-alpha-type compounds, this band appears at 899-897 cm-1. In addition, a wavy "fingerprint" pattern with two minima at 1632 (low intensity) and 1595-1594 cm-1 (high intensity) is characteristic for beta-type compounds. Our generalizations are based on spectra of cis and trans ocimene, myrcene, and dehydration products of many 3-methyl-1-alken-3-ols. Six isomers of farnesene can be characterized by GC/FT-IR. Furthermore, gas-phase IR allows the determination of the configuration of the trisubstituted double bond at C-3 in alpha-type farnesene congeners. For example, the homo- and bishomofarnesene isomers from Myrmica ants were shown to include a 3Z bond.
(Z,E)-α-Farnesene - An electroantennogram-active component of Maladera Matrida volatiles
Yarden, Gal,Shani, Arnon,Leal, Walter Soares
, p. 283 - 287 (2007/10/03)
It has previously been shown in field-trapping experiments and laboratory olfactometer bioassays that virgin females of Maladera matrida Argaman (Coleoptera, Scarabaeidae) and their volatiles, both in the presence of food (cut peanut leaves), are efficient attractants for M. matrida males and females. In this study GG-EAD experiments using male antennae and GC-MS experiments revealed that (Z,E)-α-farnesene is an active component of M. matrida female volatiles. The identification and quantitative electrophysiological responses (EAG) of synthetic (Z,E)-α-farnesene were obtained with male and female antennae. It was also shown that (Z,E)-α-farnesene is not a component of the plant volatiles that serve as synergistic components of the mixture of attractants or of the source of food for M. matrida.
Synthesis of (Z,E)- and (Z,Z)-α-Farnesenes and -Homofarnesenes
Morgan, E. David,Thompson, Lorna D.
, p. 399 - 404 (2007/10/02)
The ant substance (Z,E)-α-farnesene and its isomer (Z,Z)-α-farnesene have been synthesized in an overall yield of 34percent in six stages from methyl cyclopropyl ketone and 6-methylhept-5-en-2-one via a Wittig condensation.A mixture of the corresponding (Z,E)-α-homofarnesene of ants and its (Z,Z) isomer were prepared in much poorer yield by the same method and incompletely characterized.The isomeric identification of both insect materials were confirmed.
