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Related Concept Videos

Reactions at the Benzylic Position: Oxidation and Reduction00:59

Reactions at the Benzylic Position: Oxidation and Reduction

4.8K
The benzylic position describes the position of a carbon atom attached directly to a benzene ring. Benzene by itself does not undergo oxidation. In contrast, the benzylic carbon is quite reactive in the presence of strong oxidizing agents such as KMnO4 or H2CrO4. Therefore, alkylbenzenes are readily oxidized to benzoic acid, irrespective of the type of alkyl groups.
4.8K
Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism01:18

Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

2.6K
Birch reduction uses solvated electrons as reducing agents. The reaction converts benzene to 1,4-cyclohexadiene. The reaction proceeds by the transfer of a single electron to the ring to form a benzene radical anion. This anion is highly basic—it abstracts a proton from the alcohol to form a cyclohexadienyl radical. Another single electron transfer gives the cyclohexadienyl anion. A proton transfer from the alcohol forms 1,4-cyclohexadiene. Since this reduction occurs via radical anion...
2.6K
Hydrolysis of Chlorobenzene to Phenol: Dow Process01:10

Hydrolysis of Chlorobenzene to Phenol: Dow Process

3.8K
Simple aryl halides do not react with nucleophiles under normal conditions. However, the reaction can proceed under drastic conditions involving high temperatures and high pressure to give the substituted products. For example, chlorobenzene is converted to phenol using aqueous sodium hydroxide at 350 °C under high pressure by the Dow process. The reaction follows an elimination-addition mechanism involving a benzyne intermediate. Here, the chloride ion is...
3.8K
NMR Spectroscopy of Benzene Derivatives01:34

NMR Spectroscopy of Benzene Derivatives

10.7K
Simple unsubstituted benzene has six aromatic protons, all chemically equivalent. Therefore, benzene exhibits only a singlet peak at δ 7.3 ppm in the 1H NMR spectrum. The observed shift is far downfield because the aromatic ring current strongly deshields the protons. Any substitution on the benzene ring makes the aromatic protons nonequivalent, and the protons split each other. The peak is, therefore, no longer a singlet and the splitting pattern and their associated coupling...
10.7K
Structure of Benzene: Molecular Orbital Model01:18

Structure of Benzene: Molecular Orbital Model

11.7K
According to the molecular orbital (MO) model, benzene has a planar structure with a regular hexagon of six sp2 hybridized carbons. As shown in Figure 1, each carbon is bonded to three other atoms with C–C–C and H–C–C bond angles of 120°. The C–H bond length is 109 pm, and the C–C bond length is 139 pm which is midway between the single bond length of sp3 hybridized carbons (154 pm) and sp2 hybridized carbons (133 pm).
11.7K
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

12.4K
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.
12.4K

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Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides
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Benzyl 3-dehydr-oxy-1,2,5-oxadiazolo[3',4':2,3]oleanolate.

Jun Hu1, Xiaoyun Gong, Ruji Wang

  • 1Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology, Ministry of Education, Department of Chemistry, Tsinghua University, Beijing 100084, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online
|May 18, 2011
PubMed
Summary

This study details a novel benzyl ester derivative of oleanolic acid, a pentacyclic triterpene. Structural analysis reveals specific conformations of its fused ring system, including a unique oxadiazole moiety.

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Area of Science:

  • Organic Chemistry
  • Structural Chemistry
  • Medicinal Chemistry

Background:

  • Oleanolic acid is a naturally occurring pentacyclic triterpene with diverse biological activities.
  • Triterpene derivatives are explored for potential therapeutic applications.
  • Structural modifications of natural products can lead to novel compounds with altered properties.

Purpose of the Study:

  • To synthesize and characterize a novel benzyl ester derivative of oleanolic acid.
  • To elucidate the three-dimensional structure and conformational analysis of the synthesized compound.
  • To investigate the impact of the oxadiazole ring fusion on the triterpene scaffold.

Main Methods:

  • Chemical synthesis of the target compound, C(37)H(50)N(2)O(3).
  • Spectroscopic techniques (e.g., NMR, Mass Spectrometry) for structural confirmation.
  • X-ray crystallography or computational modeling for conformational analysis.

Main Results:

  • Successful synthesis of the benzyl ester derivative incorporating an oxadiazole ring fused to ring A.
  • The pentacyclic triterpene core exhibits specific conformational preferences.
  • Rings A and C adopt distorted half-chair conformations, while rings B, D, and E are in chair forms.

Conclusions:

  • The synthesized compound represents a unique structural modification of oleanolic acid.
  • The conformational analysis provides insights into the stereochemistry of the modified triterpene.
  • This structural information is crucial for understanding structure-activity relationships in related compounds.