Preface
Abbreviations
CHAPTER 1 OPINIONS AND SUGGESTIONS
1.1 Be a "doctor", not just be a "drug fetcher"
1.2 One a large degree, synthetic organic chemistry is still an art
1.3 Synthetic organic chemistry is an experimental science under the guidance of theory
1.4 Reduce your mistakes in your synthetic work
1.5 Your knowledge, experience, and skills never be too much
1.6 What is a mistake?
1.7 With your own ideas when you search references
1.8 Improve your decision-making ability
1.9 Knowing the mechanism of the reactions you are doing
1.10 Always learn something from the reaction you performed
1.11 Knowing reaction mechanism is not sufficient to be an excellent chemist, but it is a necessary
1.12 Patents do not tell you the full story of chemistry
1.13 Write a summary when complete a synthesis
1.14 Two examples
CHAPTER 2 GENERAL TERMS AND CONCEPTS IN SYNTHETIC ORGANIC CHEMISTRY
2.1 Reaction mechanism
2.2 The approaches to draw reaction mechanism
2.3 Desired product
2.4 Unexpected product
2.5 Side reaction
2.6 Side product and by-product
2.7 Impurity
2.8 Theoretical yield, percentage yield (yield), net yield, and overall yield
2.9 Intermediate
2.10 Transition state
2.11 Species
2.12 Free radical
2.13 Stoichiometric reaction
2.14 Catalytic reaction
2.15 Material balance
2.16 Electron balance
2.17 Nucleophile
2.18 Electrophile
2.19 Acid
2.20 Base
2.21 Acidity and pKa
2.22 Acid-base reaction
2.23 Reaction selectivity
2.24 Chemoselectivity
2.25 Regioselectivity
2.26 Stereoselectivity
2.27 Iteroselectivity
2.28 One-pot synthesis/Telescoping process
2.29 Cascade reaction
2.30 Multicomponent reaction
2.31 Flow chemistry
2.32 Atom economy
2.33 Green chemistry
2.34 Partial synthesis, total synthesis, and formal synthesis
2.35 Linear synthesis and convergent synthesis
2.36 Divergent synthesis
2.37 Click chemistry
2.38 Parallel synthesis
2.39 Solid phase synthesis
2.40 Combinatorial chemistry
2.41 Process chemist vs medicinal chemist
CHAPTER 3 GENERAL TERMS AND CONCEPTS IN MEDICINAL CHEMISTRY
3.1 What is a drug?
3.2 Drug discovery
3.3 Medicinal chemistry
3.4 Drug target
3.5 Enzyme
3.6 Receptor
3.7 Inhibitor
3.8 Activator
3.9 Drug design
3.10 Ligand-based drug design
3.11 Structure-based drug design
3.12 Lipinski's rule of five
3.13 Lead compound
3.14 Hit to lead
3.15 High-throughput screening
3.16 Pharmacophore
3.17 Affinity, efficacy, and potency
3.18 Structure-activity relationship (SAR)
3.19 Partition coefficient and Log P/Clog P
3.20 Drug candidate
3.21 Pre-clinical studies
3.22 Toxicity
3.23 Pharmacokinetics (PK) and pharmacodynamics (PD)
3.24 ADME
3.25 Bioavailability
3.26 Pharmacology
3.27 Formulation
3.28 Active pharmaceutical ingredient (API)
3.29 Drug stability
3.30 Prodrugs
3.31 Deuterium-containing drug
3.32 Antibody drug conjugate (ADC)
3.33 Good Laboratory Practice (GLP)
3.34 Good Manufacture Practice (GMP)
3.35 Chemistry, Manufacturing, and Controls (CMC)
3.36 Contract Research Organization (CRO)
3.37 Investigational New Drug Application (IND)
3.38 Clinical trials
3.39 New Drug Application (NDA)
CHAPTER 4 MECHANISM PROBLEMS FROM REACTIONS GIVE EXPECTED PRODUCTS
4.1 Formation of noncyclic compounds
4.2 Formation of hydrazine derivatives
4.3 Formation of cyclic alkane and derivatives
4.4 Formation of aromatic compounds
4.5 Formation of nonaromatic heterocycles
4.6 Formation of monocyclic aromatic heterocycles
4.7 Formation of bicyclic and polycyclic aromatic heterocycles
4.8 Miscellaneous
CHAPTER 5 MECHANISM PROBLEMS FROM REACTIONS GIVE UNEXPECTED, UNDESIRED, OR SIDE PRODUCTS
5.1 Formation of noncyclic alkane and derivatives
5.2 Formation of cyclic alkane and derivatives
5.3 Formation of aromatic compounds
5.4 Formation of nonaromatic heterocycles
5.5 Formation of monocyclic aromatic heterocycles
5.6 Formation of bicyclic aromatic heterocycles
5.7 Miscellaneous
Further Reading
Subject Index
