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Related Concept Videos

Phase I Reactions: Oxidation of Aliphatic and Aromatic Carbon-Containing Systems01:19

Phase I Reactions: Oxidation of Aliphatic and Aromatic Carbon-Containing Systems

Phase I biotransformation reactions are integral to drug metabolism, predominantly involving oxidative, reductive, and hydrolytic transformations. Chief among these are oxidative reactions, which enhance the hydrophilicity of xenobiotics and introduce polar functional groups to facilitate their elimination from the body.
Oxidation reactions are fundamental in aromatic carbon-containing systems. An example is the hydroxylation of phenobarbital, a process that transforms it into...
Aromatic Compounds: Overview01:25

Aromatic Compounds: Overview

In general, the term ‘aromatic’ indicates a pleasant smell or fragrance from fresh flowers, freshly prepared coffee, etc. In the early history of organic chemistry, many benzene derivatives were isolated from the pleasant odor oils of the plants. For example, vanillin was isolated from the oil of vanilla, methyl salicylate from the oil of wintergreen, and cinnamaldehyde from the oil of cinnamon. They all had a pleasant odor; hence the name aromatic was given.
In 1825, Faraday isolated benzene...
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Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
Adrenergic Agonists: Chemistry and Structure-Activity Relationship01:16

Adrenergic Agonists: Chemistry and Structure-Activity Relationship

Adrenergic agonists' structure-activity relationship (SAR) determines their selectivity and efficacy. These agonists comprise a phenylethylamine moiety with an aromatic ring and an ethylamine side chain.
Aromatic ring substitutions: Substituting the aromatic ring with –OH groups at positions 3 and 4 yields catecholamines (e.g., epinephrine), which have a high affinity for adrenoceptors. Hydrogen bonding between –OH groups and receptors enhances adrenergic activity.
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Oxymercuration–reduction of alkenes is one of the major reactions converting alkenes to alcohols. It involves the hydration of alkenes with mercuric acetate in a mixture of tetrahydrofuran and water, forming an organomercury adduct. This is followed by a demercuration step in which the adduct is reduced to an alcohol using sodium borohydride.
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
Due to the absence of continuous overlap of p...

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Updated: Jun 5, 2026

Synthesis of a Deuterated Standard for the Quantification of 2-Arachidonoylglycerol in Caenorhabditis elegans
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Synthesis of a Deuterated Standard for the Quantification of 2-Arachidonoylglycerol in Caenorhabditis elegans

Published on: September 21, 2019

1-De-oxy-d-arabinitol.

Sarah F Jenkinson, Filipa P Cruz, Kathrine V Booth

    Acta Crystallographica. Section E, Structure Reports Online
    |January 5, 2011
    PubMed
    Summary
    This summary is machine-generated.

    Methyl lithium addition to a lactone yielded 1-deoxy-d-arabinitol, not the expected 1-deoxy-d-ribitol. X-ray crystallography confirmed the structure of this sugar alcohol, revealing extensive hydrogen bonding in its crystal lattice.

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    Published on: March 24, 2016

    Area of Science:

    • Organic Chemistry
    • Crystallography
    • Carbohydrate Chemistry

    Background:

    • Understanding the stereochemical outcomes of reactions involving lactones is crucial in carbohydrate synthesis.
    • Methyl lithium is a common organometallic reagent used for nucleophilic addition to carbonyl compounds.

    Purpose of the Study:

    • To investigate the reaction product of methyl lithium addition to d-erythrono-1,4-lactone.
    • To determine the crystal structure of the major product using X-ray crystallography.

    Main Methods:

    • Nucleophilic addition of methyl lithium to d-erythrono-1,4-lactone.
    • Acid deprotection of the intermediate.
    • X-ray crystallography for structural elucidation.

    Main Results:

    • The major product identified was 1-deoxy-d-arabinitol (C(5)H(12)O(4)), not 1-deoxy-d-ribitol.
    • X-ray crystallography revealed the crystal structure of 1-deoxy-d-arabinitol.
    • The crystal structure features hydrogen-bonded chains running parallel to the c axis.
    • Each molecule acts as both a hydrogen bond donor and acceptor for four hydrogen bonds.

    Conclusions:

    • The reaction of methyl lithium with d-erythrono-1,4-lactone predominantly forms the arabinitol isomer.
    • The crystal structure provides detailed insights into the intermolecular interactions of 1-deoxy-d-arabinitol.