13362-52-2Relevant articles and documents
Design, Synthesis, and Biological Evaluation of the Sex Pheromone of the Asian Corn Borer, Ostrinia furnacalis (Guenée)
Lu, Zhengchang,Liu, Wei,Pan, Hongyu,Zhang, Dawei
, (2018)
A convenient total synthesis of (Z)-12-tetradecenyl acetate (1a) and (E)-12-tetradecenyl acetate (1b), which are the sex pheromones of Ostrinia furnacalis (Guenée), has been achieved. The target mixture molecules, of a cis-to-trans-isomer ratio of 27 to 73, were synthesized in 40% overall yield and through [13C + 1C] synthetic strategy in five steps from commercially available and cheap industrial brassylic acid as key starting material. The electroantennogram (EAG) responses of synthetic sex pheromone to ACB male moths were conducted. The results showed that the target mixture molecules were found to have a good activity and displayed significantly stronger EAG responses ranging from 10 to 1000 μg, and the optimized stimulating dosage of the activity of synthetic sex pheromone to ACB males is 10 μg. Compared with the existing routes, this synthetic approach is operationally simple, good-yielding, and cost-effective, which could serve as a basis for developing the techniques of sex pheromone mass trapping or mating disruption and providing an environmentally benign method to control ACB pests.
The first examples of a Meta-benzannulation from the reaction of Fischer carbene complexes with alkynes
Wang, Huan,Huang, Jie,Wulff, William D.,Rheingold, Arnold L.
, p. 8980 - 8981 (2003)
The intramolecular benzannulations of carbene complexes with alkynes are examined where the alkyne is tethered to the α-carbon of the vinyl carbene complex. These reactions are sensitive to the length of the tether and to the nature of the solvent. With a tether length of 16 methylenes, the reaction occurs in the same fashion as the intermolecular reactions to give a p-cyclophane. With intermediate tether lengths (n = 10, 13), the reaction gives an additional p-cyclophane in which the two oxygen substituents are meta on the arene ring. This type of product is unprecedented from the reaction of carbene complexes and alkynes and is quite surprising because the formation of this product requires that the carbon-carbon bond between the α- and β-carbons of the vinyl carbene complex is broken. A mechanism is proposed to account for this process which involves the crossed intramolecular [2 + 2] cycloaddition of the alkene and a ketene in a conjugated dienyl ketene to give a benzvalenone paddalane intermediate. Copyright
Heat capacities near room temperature of ten solid alkane-α, ω-diols HO-(CH2)n-OH where n = 6 and 8 ≤ n ≤ 16
Della Gatta, Giuseppe,Jozwiak, Malgorzata,Ferloni, Paolo
, p. 537 - 546 (1999)
The molar heat capacities at constant pressure Cp,m of a homologous series of alkane-α, ω-diols HO-(CH2)n-OH, where n has values of 6 and (8 to 16), were determined by using differential scanning calorimetry over the temperature range (280 to 310) K, in flowing gas. The measured values of Cp,m showed a very good linear dependence on temperature, except 1,9-nonanediol and 1,13-tridecanediol. The heat capacities at T = 298.15 K were obtained by interpolating the smoothed fitting equations as a function of temperature. The contribution to the heat capacity at T = 298.15 K of the CH2 group was derived from the slope of the Cp,m values of diols as a function of the number of carbon atoms in their molecules, and compared with the values obtained from a comprehensive collection of literature data for homologous alkyl organic compounds in the solid state. 1999 Academic Press.
Selective Reduction of Carboxylic Acids to Alcohols in the Presence of Alcohols by a Dual Bulky Transition-Metal Complex/Lewis Acid Catalyst
Gr?mer, Bendik,Saito, Susumu,Yoshioka, Shota
, p. 1957 - 1964 (2022/02/10)
Here, we report a molecular method for the generally applicable reduction of mono-and dicarboxylic acids that selectively furnishes a diverse variety of alcohols, including mono-and diols. One of the inherent drawbacks of the direct hydrogenation of carboxylic acids to alcohols is the in situ formation of the corresponding esters via condensation of the carboxylic acids with the produced alcohols. Especially, the hydrogenation of polycarboxylic acids frequently suffers from the formation of a complex mixture of oligomeric esters. This issue was successfully overcome by the combined use of a dual catalyst that consists of a bulky (PNNP)iridium complex and a Lewis acid. Owing to the steric bulk and robustness of the iridium catalyst, the main role of the Lewis acid is to independently catalyze the esterification, albeit the cooperative activation of (a resting state of) the iridium catalyst by the Lewis acid also seems to be implied.
Synthesis of 13C-labelled ω-hydroxy carboxylic acids of the general formula HO213C-(CH2)n-CH2OH or HO2C-(CH2)n-13CH2OH (n = 12, 16, 20, 28)
Schink, Carina,Spielvogel, Sandra,Imhof, Wolfgang
, p. 385 - 402 (2021/07/10)
13C-labelled ω-hydroxy-carboxylic acids HO213C-(CH2)n-CH2OH or HO2C-(CH2)n-13CH2OH (n = 12, 16, 20, 28) with 13C labels selectively introduced either at the carboxy group or at the primary alcohol function at the end of the hydrocarbon chain have been synthesized. Different synthetic strategies had to be applied depending on the position of the label, the chain length of the respective synthetic target and due to economic considerations. 13C labels in general were introduced by nucleophilic substitution of a suitable leaving group with labelled potassium cyanide and subsequent hydrolysis of the nitriles to produce the corresponding labelled carboxy functions, which may also be reduced to give the labelled primary alcohol group. All new compounds are characterized by GC/MS, IR and NMR methods as well as by elemental analysis.
METABOLICALLY STABLE PRODRUGS
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Paragraph 00119, (2020/01/24)
Provided are prodrugs of various therapeutic agents that provide enhanced bioavilabilty of the therapeutic agent, and methods of treatment conditions in a subject by administration of the one or prodrugs. As provided herein a prodrug includes a therapeutic agent covalently attached to a cap, the cap having a structure according to formula (I) where: R1 is a branched or linear substituted or unsubstituted C2-C6 alkyl, alkenyl, or alkynl; X is -S(0)2-; R2 is a branched or linear substituted or unsubstituted C4-C20 alkyl, alkenyl, or alkynyl; and R3 is -H, C3-C5 cycloalkyl, C3-C5 cycloheteroalkyl, -C(CH3)3, -CF3, -C(CF3)3, or a substituted or unsubstituted phenyl.
Systematic synthesis of novel phosphoglycolipid analogues as potential agonists of GPR55
Abe, Junpei,Ding, Feiqing,Greimel, Peter,Guy, Adam T.,Hirabayashi, Yoshio,Ito, Yukishige,Kamiguchi, Hiroyuki
supporting information, p. 8467 - 8473 (2020/11/05)
Rhodopsin-like G protein-coupled receptor (GPCR) GPR55 is attracting attention as a pharmaceutical target, because of its relationship with various physiological and pathological events. Although GPR55 was initially deorphanized as a cannabinoid receptor,
Chemical synthesis of diglucosyl diacylglycerols utilizing glycosyl donors with stereodirecting cyclic silyl protective groups
Takato, Koichi,Kurita, Motoki,Yagami, Nahoko,Tanaka, Hide-Nori,Ando, Hiromune,Imamura, Akihiro,Ishida, Hideharu
, (2019/08/01)
Chemical syntheses of the bacterial diglucosyl diacylglycerols 1-heptadecanoyl-2-pentadecanoyl-3-O-[6-O-(β-d-glucopyranosyl)-β-d-glucopyranosyl]-sn-glycerol and 1-(cis-13-octadecenoyl)-2-palmitoyl-3-O-[2-O-(α-d-glucopyranosyl)-α-d-glucopyranosyl]-sn-glycerol are described. The syntheses feature the stereoselective construction of glycosidic linkages in glycosylation reaction by utilizing glycosyl donors with stereodirecting cyclic silyl protective groups. The 1,1,3,3-tetraisopropyldisiloxane-1,3-diyl (TIPDS) group was used for formation of the β-glycosidic linkage, while the di-tert-butylsilylene (DTBS) group was used for α-linkage formation. The silyl protective groups were chemoselectively cleavable without affecting acyl functionalities on the glycerol moiety and proved effective for the synthesis of diacylglycoglycerolipids.
A Synthetic Route to the MT1-MMP Inhibitor Ancorinoside D
Petermichl, Markus,Steinert, Christine,Schobert, Rainer
, p. 730 - 738 (2019/01/23)
A methyl ester of ancorinoside D, a 3-acyltetramic acid metabolite of a sponge Penares sollasi, was synthesised in ten steps starting from a protected β- d -glucopyranosyl-(1→4)- d -galactopyranosyltrichloroacetimidate donor. Its attachment to the left half of the 3-acyl spacer by a Schmidt glycosylation, 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO)-mediated oxidation to the uronic acid, introduction of the Z -alkene via Wittig reaction, and functionalisation of the spacer terminus with Meldrum's acid gave a β-keto ester that reacted with dimethyl N -methyl- d -aspartate under neutral conditions to afford a fully protected ancorinoside D as the product of an unusual domino N -acylation-Dieckmann condensation. Global deprotection left a methyl ester of ancorinoside D, which resisted all saponification attempts.
Hydrofunctionalization of olefins to value-added chemicals: Via photocatalytic coupling
Fan, Yonghui,Li, Shenggang,Bao, Jingxian,Shi, Lei,Yang, Yanzhang,Yu, Fei,Gao, Peng,Wang, Hui,Zhong, Liangshu,Sun, Yuhan
supporting information, p. 3450 - 3456 (2018/08/06)
A green strategy was developed for the synthesis of various value-added chemicals using methanol, acetonitrile, acetic acid, acetone and ethyl acetate as the hydrogen source by coupling them with olefins over heterogeneous photocatalysts. A radical coupling mechanism was proposed for the hydrofunctionalization of olefins with methanol to higher aliphatic alcohols over the Pt/TiO2 catalyst as the model reaction. C-H bond cleavage and C-C bond formation between photogenerated radicals and terminal olefins were accomplished in a single reaction at high efficiency. Our approach is atomically economical with high anti-Markovnikov regioselectivity and promising application potential under mild reaction conditions.
