The Quantitative Inversion of cis- and trans-Alkene Isomers: A New Synthesis of Normal cis-Alkenes<sup>1</sup>

Hoff, Melvern C.; Greenlee, Kenneth W.; Boord, Cecil E.

doi:10.1021/ja01151a099

Cited by 69 publications

(8 citation statements)

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“…Liquid reagents or reagent solutions were added by syringe or cannula. Organic extracts were dried with anhydrous Na 2 SO 4 , filtered and concentrated using a rotary evaporator at aspirator pressure (20)(21)(22)(23)(24)(25)(26)(27)(28)(29)(30). Thin-layer chromatography was carried out on silica gel 60 F 254 (layer thickness 0.2 mm), and components were located by observation under UV light and/or by treating the plates with a phosphomolybdic acid or p-anisaldehyde reagent followed by heating.…”

Section: Methodsmentioning

confidence: 99%

“…for 3-5 h. [27] According to the general procedure, the reaction of 1 (220 mg, 0.982 mmol) with triphenylindium (0. (Z)-Oct-2-ene (4): [28] According to the general procedure, the reaction of 1 (243 mg, 1.084 mmol) with trimethylindium (0. (Z)-Undec-5-ene (5): [29] According to the general procedure, the reaction of 1 (238 mg, 1.062 mmol) with tri-n-butylindium [30] According to the general procedure, the reaction of 1 (215 mg, 0.959 mmol) with trivinylindium (0.…”

Section: Procedures C Palladium-catalysed Cross-coupling Reaction Of mentioning

confidence: 99%

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Palladium‐Catalysed Cross‐Coupling Reactions of Triorganoindium Reagents with Alkenyl Halides

et al. 2008

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The regio-and stereoselectivity of the palladium-catalysed cross-coupling reactions of indium organometallics with stereodefined 1-haloalkenes and 1,1-dihaloalkenes have been studied. Triorganoindium reagents (R 3 In; R = alkyl, alkenyl, aryl and alkynyl) can be stereospecifically coupled with stereodefined alkenyl iodides in good yields and short reaction times under palladium catalysis. Additionally, the palladium-catalysed cross-coupling reaction of R 3 In (90 mol-%) with 1,1-dibromo-1-alkenes gave dicoupling products in high yields. When the reaction was performed with 40 mol-% of aryl-, vinyl-and alkynylindium derivatives, trans-selective monosubstitution products were obtained in moderate to

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Section: Methodsmentioning

confidence: 99%

Section: Procedures C Palladium-catalysed Cross-coupling Reaction Of mentioning

confidence: 99%

Palladium‐Catalysed Cross‐Coupling Reactions of Triorganoindium Reagents with Alkenyl Halides

et al. 2008

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“…The solutions were prepared so that each animal received 0.033 ml/10 g of body weight. Mice were sacrificed by decapitation at various time intervals (5,10,20,30, or 45 min) following administration and the brain and liver were removed from the carcass, rinsed with saline, blotted dry, weighed, and homogenized with 4.5 (brain) or 4.0 ml (liver) of 0.01 N HCl in glass tissue grinders. Each brain or liver homogenate was mixed with 5 µg each of unlabeled iV-alkylnormeperidine hydrochloride and unlabeled normperidine hydrochloride, and 0.5 nCi of [14C]-lV-butylnormeperidine hydrochloride which was employed as an internal standard.…”

Section: Methodsmentioning

confidence: 99%

Relation between analgetic ED50 dose and time-course brain levels of N-alkylnormeperidine homologs

Larson

Portoghese

1976

J. Med. Chem.

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The brain levels of meperidine and three N-alkyl homologues were determined at equal analgetic iv doses in mice. The relative levels of the four compounds in brain were found to be closely proportional to their ED50 doses even though the compounds exhibit a wide range in partition coefficient and metabolic N-dealkylation. While lipid solubility and metabolism are undoubtedly important factors in the overall time-course brain levels, it appears that during the period of analgetic measurement (5-60 min after injection) these factors do not profoundly affect the relative brain levels because peak uptake occurs within the first 5 min after administration of the homologues. As a consequence, the observed ED50 potencies appear to provide a fair approximation of the relative receptor affinities of the four homologues. N-Dealkylation was observed as a major metabolic transformation by mouse liver in vivo for all four compounds, and the extent of this N-dealkylation was found to directly correspond to the rates of N-dealkylation by mouse liver homogenate seen in an earlier study.

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“…Male albino Sprague-Dawley derived rats of weight 200-710 g obtained from Harlan or Lab Supply, Cumberland, Ind., were used in this study. The rats received 5 mg/kg of reserpine ip [18][19][20][21][22] hr prior to the experiment. The animals were decapitated and the vas deferens was quickly removed, cleaned of blood vessels and fatty tissue, and mounted in a 10-ml jacketed tissue bath containing modified Krebs solution of the following composition as millimoles per liter in double distilled water: NaCl, 118; KC1, 4.7; MgClz-6HzO, 0.54; Ca-•2 , 2.5; NazHPCU, 1.0; NaHCOa, 25; glucose, 11.…”

Section: -Cyclooctenyl-2-hydroxyethylamine Hydrochloride (5a)mentioning

confidence: 99%

Importance of the aromatic ring in adrenergic amines. 2. Synthesis and adrenergic activity of some nonaromatic six- and eight-membered ring analogs of .beta.-phenylethanolamine

Grunewald¹,

Grindel²,

Patil³

et al. 1976

J. Med. Chem.

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The synthesis of beta-phenylethanolamine analogs in which the phenyl ring is replaced by cyclohexyl, cyclohexen-4-yl, cyclooctyl, cyclooctenyl, cycloocta-1,3-dien-2-yl, cycloocta-1,5-dienyl, and cyclooctatetraenyl was accompanied by conversion of the corresponding aldehydes to the cyanohydrins followed by reduction with lithium aluminum hydride. A preparatively useful synthesis of 1-formylcyclooctatetraene is described utilizing the photocycloaddition of methyl propiolate to benzene followed by reduction to the alcohol and oxidation with MnO2. All compounds, as their hydrochloride salts, exhibited indirect adrenergic activity on the rat vas deferens. On the reserpinized rat vas deferens all compounds potentiated the effects of exogenous norepinephrine. The results are in agreement with the conclusion that the more saturated the ring moiety, the greater the affinity for the amine uptake site of the vas deferens and suggest that there is no important interaction between the drug and this uptake site that involves pi-complex formation.

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The Quantitative Inversion of cis- and trans-Alkene Isomers: A New Synthesis of Normal cis-Alkenes¹

Cited by 69 publications

References 0 publications

Palladium‐Catalysed Cross‐Coupling Reactions of Triorganoindium Reagents with Alkenyl Halides

Palladium‐Catalysed Cross‐Coupling Reactions of Triorganoindium Reagents with Alkenyl Halides

Relation between analgetic ED50 dose and time-course brain levels of N-alkylnormeperidine homologs

Importance of the aromatic ring in adrenergic amines. 2. Synthesis and adrenergic activity of some nonaromatic six- and eight-membered ring analogs of .beta.-phenylethanolamine

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The Quantitative Inversion of cis- and trans-Alkene Isomers: A New Synthesis of Normal cis-Alkenes1

Cited by 69 publications

References 0 publications

Palladium‐Catalysed Cross‐Coupling Reactions of Triorganoindium Reagents with Alkenyl Halides

Palladium‐Catalysed Cross‐Coupling Reactions of Triorganoindium Reagents with Alkenyl Halides

Relation between analgetic ED50 dose and time-course brain levels of N-alkylnormeperidine homologs

Importance of the aromatic ring in adrenergic amines. 2. Synthesis and adrenergic activity of some nonaromatic six- and eight-membered ring analogs of .beta.-phenylethanolamine

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The Quantitative Inversion of cis- and trans-Alkene Isomers: A New Synthesis of Normal cis-Alkenes¹