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The algebra of organic synthesis : green metrics, design strategy, route selection, and optimization / John Andraos

Author:
Andraos, John
Published:
Boca Raton : CRC Press, [2012 ]+.
1 CD-ROM 4 3/4 in.
Copyright Date:
©2012
Physical Description:
xvii, 1,203 pages : illustrations ; 27 cm

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Contents:
Machine generated contents note: ch. 1 Aims and Scope -- 1.1.What Does This Book Offer? -- 1.2.Chapter Descriptions -- 1.3.Synthesis Plan Database -- 1.4.How to Use Synthesis Database Compilation -- Bibliography -- ch. 2 General Comments on Organic Chemistry and Green Chemistry -- 2.1.Getting Our House in Order -- 2.1.1.Education -- 2.1.1.1.Rules for Writing Reaction Mechanisms -- 2.1.2.Literature -- 2.2.Research Trends in Organic Synthesis -- 2.3.Research Trends in Green Chemistry -- 2.4.Green Chemistry Trends in Industry -- References -- ch. 3 Problems with Literature Reporting of Synthesis Plans -- 3.1.Introduction -- 3.2.Missing Information in Plans -- 3.3.Mistakes in Reported Yields and Amounts of Materials Used -- 3.4.Mismatches in Reported Reaction Yields -- 3.5.Tactics to Artificially Amplify Reaction Performance -- 3.6.Reporting of Classical Resolutions -- 3.7.Exaggerated Claims of Efficiency -- 3.8.Good "Greening" Progression but Little Detail to Substantiate Claim -- 3.9."Readily Available Starting Materials" -- 3.10.Biotransformations Not Revealing Reaction Yields in Usual Way -- 3.11.Papers Describing Reactions Using Microwave Irradiation -- 3.12.Reviewing of Scientific Papers -- 3.13.Patents -- References -- ch. 4 Problems and Challenges in Synthesis and Green Chemistry -- 4.1.Philosophy and Practice of Chemistry -- 4.2.Education -- 4.3.Chemistry Literature -- 4.4.Reaction Performance Improvements -- 4.5.Synthesis Performance -- 4.6.Metrics -- 4.7.Reaction Mechanism -- References -- ch. 5 Overview of Green Metrics -- 5.1.Advantages of Using Green Metrics -- 5.2.Material Efficiency Metrics and Visuals -- 5.3.Strategy Efficiency Metrics and Visuals -- 5.4.Hypsicity (Oxidation Level) Analysis -- 5.4.1.Introduction -- 5.4.2.Synthesis Plans -- 5.4.2.1.Ozonolysis -- 5.4.2.2.Dihydroxylation -- 5.4.2.3.Generation of Diauzomethane -- 5.4.2.4.Tracking Origin of Sulfur Atom in Saccharin Synthesis -- 5.5.Instructions on Using PENTAGON, LINEAR, and CONVERGENT Spreadsheets -- 5.6.Mathematical Derivations and Analysis -- 5.6.1.Derivation of Expression for Overall E-Factor for Any Chemical Reaction -- 5.6.2.Connection between Stoichiometric Factor and Mole Percent Excess Reagent -- 5.6.3.Percent Conversion and Percent Selectivity -- 5.6.4.Derivation of Expressions Relating AE and E(mw), and Overall RME and E-Factor -- 5.6.5.Derivation of Golden Ratio Threshold for "Green" Reactions -- 5.6.6.Expression for E-Total for Any Chemical Reaction as a Sum of Contributors -- 5.6.7.Expression for E-Total for a Synthesis Plan as a Sum of Contributors -- 5.6.8.Expression for Raw Material Cost of Target Product for Any Chemical Reaction -- 5.6.9.Expression for Raw Material Cost of Target Product for Any Synthesis Plan -- 5.6.10.Expression for Finding Centroid of Final Product Node in Synthesis Tree -- 5.6.11.Expression for MW First Moment -- 5.6.12.Expression for /(sac) -- 5.6.13.Algorithm for LINEAR-COMPLETE and CONVERGENT-COMPLETE Spreadsheets -- 5.6.14.Note on Auge Method -- 5.7.Complete Worked-Out Examples -- 5.7.1.Guaifenesin -- 5.7.2.Probueanol -- 5.7.3.Leonurine -- References -- ch. 6 Optimization -- 6.1.Introduction -- 6.2.Worked-Out Radial Pentagon Examples -- 6.3.Radial Hexagon Analysis -- 6.4.Connectivity Analysis -- 6.5.Probability Analysis -- 6.6.An Eight-Component Coupling -- References -- ch. 7 Named Organic Reaction Database -- 7.1.Categorization of Named C-C Coupling/Addition/Cyclization Reactions by Minimum Atom Economy and Maximum Environmental Impact Factor, Maximum Molecular Weight Fraction of Sacrificial Reagents, Hypsicity Index -- 7.2.Categorization of Named Condensation Reactions by Minimum Atom Economy and Maximum Environmental Impact Factor, Maximum Molecular Weight Fraction of Sacrificial Reagents, Hypsicity Index -- 7.3.Categorization of Named Elimination/Fragmentation Reactions by Minimum Atom Economy and Maximum Environmental Impact Factor, Maximum Molecular Weight Fraction of Sacrificial Reagents, Hypsicity Index -- 7.4.Categorization of Multicomponent Reactions by Minimum Atom Economy and Maximum Environmental Impact Factor, Maximum Molecular Weight Fraction of Sacrificial Reagents, Hypsicity Index -- 7.5.Categorization of Named Non-C-C Coupling/Addition/Cyclization Reactions by Minimum Atom Economy and Maximum Environmental Impact Factor, Maximum Molecular Weight Fraction of Sacrificial Reagents, Hypsicity Index -- 7.6.Categorization of Named Oxidation Reactions (with respect to Substrate of Interest) by Minimum Atom Economy, Maximum Environmental Impact Factor, Maximum Molecular Weight Fraction of Sacrificial Reagents, Hypsicity Index -- 7.7.Categorization of Named Rearrangement Reactions by Minimum Atom Economy and Maximum Environmental Impact Factor, Maximum Molecular Weight Fraction of Sacrificial Reagents, Hypsicity Index -- 7.8.Categorization of Named Reduction Reactions (with respect to Substrate of Interest) by Minimum Atom Economy, Maximum Environmental Impact Factor, Maximum Molecular Weight Fraction of Sacrificial Reagents, Hypsicity Index -- 7.9.Categorization of Named Sequences by Minimum Atom Economy and Maximum Environmental Impact Factor, Maximum Molecular Weight Fraction of Sacrificial Reagents, Hypsicity Index -- 7.10.Categorization of Named Substitution Reactions by Minimum Atom Economy and Maximum Environmental Impact Factor, Maximum Molecular Weight Fraction of Sacrificial Reagents, Hypsicity Index -- 7.11.Summary of Trends in Named Organic Reaction Database -- ch. 8 Example Transformations Illustrating Sacrificial Reagents -- 8.1.Single-Step Reactions -- 8.2.Two-Step Reactions -- 8.3.Sacrificial Reactions from Synthesis Database -- References -- ch. 9 Synthesis Strategies -- 9.1.Brainstorming Exercises -- 9.1.1.Nitrile to Carboxylic Acid Transformation -- 9.1.2.Making a Methyl Ester -- 9.1.3.Making an Amide -- 9.1.4.Cyclohexanone Ring Construction -- 9.2.Direct Syntheses -- 9.3.Indirect Syntheses -- 9.4.Choice of Starting Materials for Synthesis -- 9.5.Comparison of Total Synthesis versus Semisynthesis -- 9.6.Bio-Inspired Strategies -- 9.7.Chemoselectivity versus Classical Resolution Comparison -- 9.8.Mismatch between Strategy and Waste Production -- 9.9.Route Selection and Reaction Networks -- 9.10.Scheduling -- 9.11.What Can Go Wrong with Computer-Assisted Synthesis Software -- References -- ch. 10 Ring Construction Strategies -- 10.1.Ring Construction Strategies in Synthesis Database -- 10.2.Ring Contractions in Named Organic Reaction Database -- 10.3.Ring Expansions in Named Organic Reaction Database -- 10.4.Bicyclic Formation Reactions in Named Organic Reaction Database -- 10.5.Sacrificial Rings -- 10.6.Use of the Furan Ring -- 10.7.Wender [x + y + z] Ring Construction Strategies -- 10.8.Spectacular Ring Construction Strategies -- 10.9.Proposal for a Computer-Searchable Ring Construction Database -- Reference -- ch. 11 Example Highlights from Database -- 11.1.Which Plan to Choose for Scale-Up? -- 11.2.Sparse Target Bond Making Profiles -- 11.3.Recycling Options -- 11.4.Improvement in Waste Reduction -- 11.5.Spectacular Examples of Synergy between Strategy and Material Efficiency Metrics -- 11.6.MicroChannel and Flow Technique Strategies -- 11.7.Ring Construction Novelty -- 11.8.Wrong Starting Materials Used -- 11.9.Plan with No Target Bonds Made -- 11.10.Old Reactions Using One of 12 Principles of Green Chemistry -- 11.11.Telescoping Steps -- 11.12.Extreme Convergence in Plans -- 11.13.Use of a Hub Common Intermediate -- 11.14.Compromise between Strategy and Material Efficiencies -- 11.15.Inclusion of Syntheses of Catalysts and Ligands for Complete Analysis -- 11.16.Synthesis Plans Tracing Back to Common Starting Materials for Fairest Comparisons -- 11.17.Most Challenging Molecule to Synthesize: Colchicine -- 11.18.Target Compound Where Fundamental Named Organic Reactions Were Discovered -- 11.19.Contrast between Classical and Modern Chemical Routes -- 11.20.Resolution with Lipase -- References -- ch. 12 Summary of Overall Trends in Synthesis Database -- 12.1.Overall Atom Economy Trends -- 12.2.Overall Yield Trends -- 12.3.Kernel Overall Reaction Mass Efficiency Trends -- 1.2.4.Degrees of Convergence and Asymmetry Trends -- 12.5.Target Bond Forming Profile Parameters -- 12.6.Sacrificial Reagents and Sacrificial Reaction Trends -- 12.7.Hypsicity Trends -- References -- ch. 13 Compounds with Multiple Plans -- Appendix A -- A.1.Tables of Densities of Solvents and Work-Up Solutions Used in Radial Pentagon Analyses -- A.2.List of Abbreviations for Reagents -- A.3.List of Abbreviations for Functional Groups -- A.4.List of Chiral Auxiliaries Used in Synthesis Plans -- A.5.List of Plans with Steady Building Up MW Profile -- A.6.Summary Tables for Trends in Reaction Database -- A.6.1.List of Plans That Are Isohypsic (HI = 0 with No Algebraic Cancellations of "Ups" and "Downs") -- A.6.2.List of Plans That Are Isohypsic (HI = 0 as a Consequence of Algebraic Cancellations of "Ups" and "Downs") -- A.6.3.List of Plans That Are Hyperhypsic (HI > 0) -- A.6.4.List of Plans That are Hypohypsic (HI < 0) -- A.6.5.List of Plans That Involve Chemo-Enzymatic Steps -- A.6.6.List of Plans by Final Product That Transform a Starting Natural Product into Another Target Natural Product -- A.7.Monocyclic and Bicyclic Ring Enumeration Database -- A.7.1.List of Plans Involving Constructing Three-Membered Monocyclic Rings -- A.7.2.List of Plans Involving Constructing Four-Membered Monocyclic Rings -- A.7.3.List of Plans Involving Constructing Five-Membered Monocyclic Rings -- A.7.4.List of Plans Involving Constructing Six-Membered Monocyclic Rings -- A.7.5.List of Plans Involving Constructing Seven-Membered Monocyclic Rings -- A.7.6.List of Plans Involving Constructing Eight-Membered Monocyclic Rings -- A.7.7.List of Plans Involving Constructing Nine-Membered Monocyclic Rings -- A.7.8.List of Plans Involving Constructing 10-Membered Monocyclic Rings -- and Contents note continued: A.7.9.List of Plans Involving Constructing 15-Membered Monocyclic Rings -- A.7.10.List of Plans Involving Constructing Bicyclic Rings -- A.7.11.List of Plans Involving Constructing Tricyclic Rings -- A.7.12.List of Plans Involving Constructing Quadricyclic Rings -- A.7.13.List of Plans Involving Rearrangements from One Ring Type to Another -- A.7.14.List of Named Organic Reactions Involving Ring Constructions -- A.7.15.Enumeration of Bond Disconnections by Ring Size for Monocyclic Rings -- A.7.16.Enumeration of Monocyclic Ring Construction Templates -- A.7.17.Enumeration of Bond Disconnections by Ring Size for Fused Bicyclic Rings -- A.7.18.Enumeration of Fused Bicyclic Ring Construction Templates -- A.7.19.Enumeration of Bond Disconnections by Ring Size for Bicyclic Rings -- A.8.Di-Substituted Aromatic Combinations Using Donor and Acceptor Groups -- A.9.Tri-Substituted Aromatic Combinations Using Donor and Acceptor Groups -- A.10.Glossary of Terms Used in Organic Synthesis -- A.11.Presidential Green Chemistry Challenge Awards Administered by the U.S. Environmental Protection Agency (EPA) -- A.11.1.Greener Synthetic Pathways Award Category -- A.11.2.Academic Awards Category -- A.11.3.Greener Reaction Awards Category -- A.11.4.Designing Greener Chemicals Award Category -- A.11.5.Small Business Award Category -- A.12.Worked Out Atom Economies for Reactions Cited in Trost's 1991 Paper on Atom Economy -- A.12.1.Cycloadditions -- Appendix B Challenging Redox Reactions from Synthesis Database.
Summary:
"A how-to manual for quantitative analysis of material efficiency and synthesis strategy in chemistry, this book explains quantitative material efficiency and discusses the role of metrics analysis in actualizing the principles of green chemistry. It covers graph theory as it applies to organic synthesis, the simple mathematical analysis of organic synthesis, and how synthesis plants can be ranked in an unbiased way. The author illustrates the concepts with example target plans and classical targets considered milestones in synthetic chemistry from pharmaceuticals, dyestuffs, agrichemicals, insecticides, natural products, and molecules of theoretical interest"--
Subject(s):
ISBN:
9781420093285 (hardback)
1420093282 (hardback)
Bibliography Note:
Includes bibliographical references and index.
View MARC record | catkey: 8163247