دانلود کتاب Organoselenium Chemistry: Between Synthesis and Biochemistry

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Organoselenium Chemistry: Between Synthesis and Biochemistry
Copyright
Dedication
Contents
Foreword
Preface
List of Contributors
1. Introduction
Abstract
1.1 Overview on Organoselenium Compounds
Acknowledgement
Conflict of Interest
References
2. Electrophilic Selenium Reagents: Addition Reactions to Double Bonds and Selenocyclizations
Abstract
2.1. General Aspects of Selenenylation and Selenocyclization Reactions
2.2 Synthesis of Electrophilic Selenium Reagents
2.3. Addition Reactions to Double Bonds
2.3.1. Mechanism of Selenenylation of Alkenes
2.3.2. Oxyselenenylation
2.3.3. Azaselenenylation
2.3.4. Carboselenenylation
2.4. Selenocyclizations
2.4.1. Oxyselenocyclization
2.4.2. Azaselenocyclization
2.4.3. Carboselenocyclization
Acknowledgement
Conflict of Interest
References
3. Nucleophilic Selenium: Nucleophilic Substitution
Abstract
3.1 Introduction
3.2. Preparation of Nucleophilic Selenium Species
3.3. Reactions of Nucleophilic Selenium Species
3.3.1. Reactions with Alkyl Halides, Tosylates and Acetates
3.3.2. Reactions with Aryl Halides, Aryl Boronic Acids and Diaryl Iodonium Salts
3.3.3. Reactions with Vinyl-Halides, -Boronic Acids, -Iodonium and - Trifluroborate Salts
3.3.4. Attack at an Acyl Carbon
3.3.4.1. Reactions with Acid Chlorides and Anhydrides
3.3.4.2. Reactions with Chloroformates and Carbamyl Chlorides
3.3.5. Ring Openings by Nucleophilic Selenium
3.3.5.1. Epoxides and Cyclic Ethers
3.3.5.2. Aziridines
3.3.5.3. Cyclopropanes
3.3.6. Reactions with Esters and Lactones
3.3.7. Miscellaneous
3.4. Applications to Solid-Phase Synthesis
Conclusion and Outlook
Acknowledgement
Conflict of Interest
References
4. Organoselenium Compounds as Precursor of Radicals
Abstract
4.1 Introduction
4.2. Alkyl Phenyl Selenides as the Source of Radicals
4.3. Acyl Phenyl Selenides as the Source of Radicals
4.4. Imidoyl Phenyl Selenides as the Source of Radicals
4.5. Phenylselenol as the Source of Radicals
4.6. Other Selenides as the Source of Radicals
Acknowledgement
Conflict of Interest
References
5. Hypervalent Selenium Derivatives
Abstract
5.1. Introduction
5.2. Reactive Intermediates Containing a Hypervalent Selenium Atom
5.3. Isolable Selenuranes
5.3.1. 10-Se-3 Selenuranes
5.3.2. 10-Se-4 Selenuranes
5.3.3. Isolable Selenurane Oxides (10-Se-5 Species)
5.4. Isolable 12-Se-6 Perselenuranes
5.5. Isolable 12-Se-5 Perselenuranes
Acknowledgement
Conflict of Interest
References
6. Selenoamides, Synthetic Methods and Recent Progress on their Synthetic Applica
Abstract
6.1 Introduction
6.2. Selenoamides: Synthetic Methods
6.2.1. Amides to Selenoamides
6.2.2. Nitriles to Selenoamides
6.2.3. Acetylenes to Selenoamides
6.2.4. Miscellaneous
6.3. Selenoamides: Recent Progress on Their Synthetic Applications
6.3.1. Intermolecular Cyclization
6.3.2. Selenoiminium Salts
6.3.3. Copper(0)-Induced Reaction of Selenoamides
6.3.4. Deprotonation of Selenoamides
6.3.5. Photoinduced Reaction
Conclusion and Outlook
Acknowledgement
Conflict of Interest
References
7. Enantioselective Catalysis for the Preparation of Organoselenium Compounds and Applications
Abstract
7.1 Introduction
7.2. Synthesis of Chiral Organoselenium Compounds by Organometallic Catalysis and Applications
7.3. Synthesis of Chiral Organoselenium Compounds by Organocatalysis and Applications
7.4. Synthesis of Organoselenium Compounds by Biocatalysis
7.5 Conclusion
Acknowledgement
Conflict of Interest
References
8. Eco-Friendly Access and Application of Organoselenium Reagents: Advances Toward Green Chemistry
Antonio L. Braga1,*, Ricardo S. Schwab2,* and Oscar E.D. Rodrigues3
Abstract
8.1 Introduction
8.2. Green Approaches to the Synthesis of Organoselenium Compounds
8.2.1. Ionic Liquids as Recyclable Solvents
8.2.2. Water
8.2.3. Glycerol, Ethanol and Polyethylene Glycol
8.2.4. Solvent-Free
8.3. Green Application of Organoselenium Reagents as Catalysts
8.3.1. Selenenylation-Deselenenylation Reaction
8.3.2. Baeyer-Villiger Reaction
8.3.3. Oxidation of Carbon-Carbon Double Bonds
8.3.4. Oxidative Bromination
8.3.5. Miscellaneous Reactions
Acknowledgement
Conflict of Interest
References
9. Biochemistry and Nutrition of Selenium: From Inorganic Forms to Endogenous Proteins
Abstract
9.1 Introduction
9.2. The Food Chain of Selenium
9.3. Metabolism and Bioavailability
9.4. Daily Requirements and Intake
9.4.1. Daily Requirements
9.4.2. Actual Intake as Measured by Surrogate Biomarkers of Se Status
9.5. Selenium Toxicity
9.5.1. No Observed Adverse Effect Level (NOAEL) and Tolerable Upper Intake Level (UL)
9.6. Dietary Sources
9.6.1. Meat, Chicken, Fish and Eggs
9.6.2. Fruits and Vegetables
9.6.3. Nuts, Legumes and Cereals
9.6.4. Milk and Dairy Products
9.6.5. Miscellaneous
9.6.6. Dietary Supplements
9.7. Selenium Deficiency
9.7.1. Endemic Forms
9.7.2. Se and Thyroid Hormones
9.8. Health Promoting and Adverse Effects
9.8.1. Se and Cancer
9.8.2. Se and Diabetes
9.8.3. Se and Cardiovascular Disease
9.8.4. Immune Function and Susceptibility to Viral Infections
9.8.5. Se and Mood Disorders
9.9. Biochemistry and Molecular Biology of Sec and Selenoproteins (Table 9.6)
9.9.1. Why do Selected Proteins have Substituted Cys with Sec?
9.9.2. Selenoproteins: General Characteristics
Acknowledgement
Conflict of Interest
References
10. Antimicrobial Activity of Organoselenium Compounds
Abstract
10.1 Introduction
10.2. Antimicrobial Activity
10.2.1. Ebselen
10.2.2. Selenoquinoline
10.2.3. Diselenides
10.2.4. Selenomorpholines
10.2.5. Piperidines
10.2.6. Pyridazines
10.2.7. Selenoazoles
10.2.8. Gold(I)Phosphine Complexes Containing Se Ligands
10.2.9. Amino Acid Derivatives Containing Se
10.2.10. Dideoxynucleoside Analogues
10.2.11. Imidazolium Ionic Liquids Containing Se
10.3. Application of Organoselenium Compounds
10.3.1. Food Preservatives
10.3.2. Pesticides
10.3.3. Dietary Supplement
10.3.4. Wound Dressing
10.4. Conclusion and Outlook
Acknowledgement
Conflict of Interest
References
11. Selenium and “Bio-Logic” Catalysis: New Bioinspired Catalytic Reactions
Abstract
11.1 Introduction
11.2. Artificial Selenoenzymes
11.3. Bioinspired Selenocatalysts
11.3.1. ID Mimics
11.3.2. GPx Mimics and “Bio-Logic” Approach
11.4. Conclusion and Outlook
Acknowledgement
Conflict of Interest
References
12. Antioxidant Organoselenium Molecules
Abstract
12.1 Introduction
12.2. Regulation of Oxidative Stress Using SeAO
12.3. Selenium AO
12.4. Interaction of Selenium AO with ROS
12.5. Selenium PO
12.6 Conclusion and Outlook
Acknowledgement
Conflict of Interest
References
77Se NMR: Theoretical Aspects and Practical Applications
Abstract
13.1 Introduction
13.2 The Oretical Background of NMR Spectroscopy
13.2.1. Hamiltonian for Diamagnetic Molecules in the External Magnetic Field
13.2.2. Theoretical Treatments of Magnetic Shielding Tensors σ
13.2.3. Theoretical Treatments of Indirect Nuclear Spin-Spin Coupling Tensor J
13.3. Developments in Calculations of 77Se NMR Chemical Shifts
13.3.1. Early Development to Calculate σ(Se) with Gaussian-Type Atomic Orbitals
13.3.2. Application of σ(Se) to Orientational Effect in Aryl Selenides
13.3.3. Examination of Basis Set System to Obtain the Reliable σ(Se)
13.3.4. Development to Calculate σ(Se) with Slater-Type Atomic Orbitals
13.4. Basic Information Derived from Calculated σ(Se)
13.4.1. Origin of δ(Se): pre-α, α, β, γ and δ Effects
13.4.2. Contributions from Atomic p(Se), d(Se) and f(Se) Orbitals to σp(Se)
13.4.3. Charge Effect on σ(Se): Evaluation of Electron Population Terms
13.5. Applications of 77Se NMR
13.5.1. Determination of Structures and Detection of Intermediates in Solution
13.5.2 Structural Determination of Arylselenides in Solutions: Orientational Effect on δ(Se)
13.6. Calculations of Nuclear Spin-Spin Coupling Constants
13.6.1. 1J(Se, X: X = C and F)
13.6.2. 1J(Se, Se)
13.7. Indices for Aromaticity: Nucleus Independent Chemical Shifts, NICS
13.8. Relativistic Effect
13.8.1. Survey of Relativistic Effect
13.8.2. Relativistic Effect on σ(Se)
13.8.3. Relativistic Effect on J(Se, X)
13.9. Conclusion and Outlook
Acknowledgement
Conflict of Interest
References
Index
A
B
C
D
E
F
G
H
I
K
L
M
N
O
P
R
S
T
U
V
W
Z
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