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Related Concept Videos

E2 Reaction: Stereochemistry and Regiochemistry02:43

E2 Reaction: Stereochemistry and Regiochemistry

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Elimination reactions of alkyl halides can yield one or more alkenes depending on the specific regiochemical and stereochemical considerations. While the regiochemistry of the reaction governs the location of the double bond in the product, the stereochemical requirements often influence the geometry.
When a substrate with two different β hydrogens undergoes an E2 elimination, the presence of a strong base can yield two regioisomeric alkenes. The more-substituted alkene is the major...
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E2 Reaction: Kinetics and Mechanism02:45

E2 Reaction: Kinetics and Mechanism

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SN2 substitutions and E2 eliminations of alkyl halides proceed via a concerted pathway. While the nucleophile attacks the alpha carbon in SN2 reactions, it functions as a strong base and abstracts a beta hydrogen in the E2 mechanism. The rate-limiting transition state in E2 elimination reactions is characterized by partially broken carbon–hydrogen and carbon–halogen bonds and a partially formed pi bond between the alpha and beta carbons. The beta hydrogen and halide are eliminated...
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Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

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Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
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Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

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Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
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Preparation of Epoxides03:00

Preparation of Epoxides

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Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...
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Alkylation of β-Diester Enolates: Malonic Ester Synthesis01:14

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Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.
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β-Elemene derivatives produced from SeO2-mediated oxidation reaction.

Xingrui He1,2,3,4, Xiao-Tao Zhuo1,2,3, Yuan Gao5

  • 1Key Laboratory of Elemene Class Anti-Cancer Chinese Medicine of Zhejiang Province, Hangzhou Normal University, Hangzhou, Zhejiang 311121, People's Republic of China.

Royal Society Open Science
|June 16, 2020
PubMed
Summary

Researchers developed a new one-step SeO2-mediated oxidation to create novel beta-elemene derivatives. These compounds exhibit enhanced anti-proliferation activity against cancer cells, with compound 17 showing significant efficacy.

Keywords:
SeO2anti-proliferationcyclohexyl ring modificationsβ-elemene

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Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry

Background:

  • Beta-elemene is a natural compound with known anti-cancer properties.
  • Modifications to beta-elemene are explored to enhance its therapeutic potential.
  • Targeting the cyclohexyl ring offers a new avenue for beta-elemene derivatization.

Purpose of the Study:

  • To develop a novel synthetic route for beta-elemene derivatives.
  • To explore modifications on the cyclohexyl ring of beta-elemene.
  • To evaluate the anti-proliferation activity of new beta-elemene derivatives against cancer cell lines.

Main Methods:

  • Selenium dioxide (SeO2)-mediated oxidation reaction.
  • One-step synthesis of beta-elemene derivatives.
  • Structure elucidation using 2D-Nuclear Magnetic Resonance (2D-NMR) techniques.
  • In vitro anti-proliferation assays on A549 and U-87MG cancer cell lines.

Main Results:

  • Successful synthesis of multiple new beta-elemene derivatives via a single-step oxidation.
  • First reported modifications on the cyclohexyl ring of beta-elemene.
  • New derivatives demonstrated superior anti-proliferation activity compared to beta-elemene.
  • Compound 17 exhibited the most potent anti-proliferation effects on A549 and U-87MG cells.

Conclusions:

  • A novel and efficient method for accessing oxidative beta-elemene derivatives has been established.
  • The developed method allows for facile derivatization of the beta-elemene cyclohexyl ring.
  • The synthesized beta-elemene derivatives hold promise as potential anti-cancer agents, particularly compound 17.