September 2, 2015 Reaxys: - an introduction and training presented to CALIS members Ms. Doreen Tan 陈慧敏 Senior Product Sales Manager, Life Science, Asia Pacific Dr. Ping Yin 尹平 Reaxys Trainer 培训讲师

2 2. What is Reaxys: Content and Navigation Concept Reaxys supports research and fuels discovery by integrating reaction and substance data search with synthesis planning. Easy access to relevant, actionable results means chemists in R&D and academia can move quickly through the steps in their workflow and deliver superior outcomes.

What is Reaxys? Experimentally validated content built upon more than 100 years tradition with Beilstein and Gmelin Gmelin PCD Reaxys Beilstein Data consolidated into a single view Excerpted by trained chemists, Quality checked by trained chemists, process managed and overseen by PhD chemists Abstracting sources and extracting data relevant to synthetic chemists Only experimentally validated data is included – no calculated or extrapolated data Customer and Reaxys Board Development partner - driven development Beilstein: Selected organic chemistry patent publications Gmelin: Selected core chemistry journals since 1771 (organic, metallorganic, inorganic chemistry) PCD: Selected organic chemistry patent publications since 1976

Why use Reaxys now? Using innovative methods Elsevier ensures it’s products meet the market needs and are user friendly. Innovations in publishing and searching data enable you to be more efficient Innovative techniques offer new insights, new approaches to asking questions, new ways of thinking The connection between Magnesium-Deficiency and Migraine was found cross-searching publications in different scientific areas – this is a strong proof that innovation advances science Our Innovations enable YOU to be innovative in Chemistry

Chemical Structure Relate it Measure it Make it Modify it ephedrine adrenaline isoprenaline etc. Buy it Salbutamol ephedrine Intrinsic and extrinsic Properties Related structures and properties Innovation in navigation

 Additional content: Patent Chemistry Database (PCD) --- patent documents from  Harmonised content of Beilstein, Gmelin and PCD --- extensive repository of chemical properties and reaction data presented with chemistry as the organizing principle.  Innovative workflow tool with simple interface and new powerful analysis and planning tools to that help to plan the synthesis of target compounds efficiently  Web-based, no installation efforts required. Simply access at  Continuous updated product with no service interruption to consortium members.  Elsevier now provides technical & scientific and phone support with Chinese speaking product specialists Benefits of migration to Reaxys

Anyone, from students to professionals, who needs accurate and instant information on chemical synthesis, structural, spectroscopic, biological, chemical & physical property data Medicinal Chemists Cheminfomatics Synthetic Chemists Process Engineers Chemical Engineers Material Scientists Who is Reaxys for?

8 3. Training / Live Demonstration Dr. Ping Yin 尹平 Reaxys Trainer 培训讲师

9 3. Worked example Salbutamol

Worked Example: Salbutamol Typically a chemist would want to know:  How can Salbutamol be synthesized? Process details? Yields? Patents?  How to buy or synthesize the starting materials? Supplier data? Reactivity?  How does Salbutamol react with other substances to produce new compounds?  Are there spectral or physical data to identify the compound?  Which bioactivity and application data does it have?  Which analogous compounds exist, and how do their properties compare to those of Salbutamol?  Which key publications should I read? The following search scenario demonstrates how Reaxys can be used to answer such questions.

1 2 1: Select "Reactions" to search for the preparation of a substance 2: Click "Generate Structure from Name" to create a structure query Worked example: SALBUTAMOL

1 2 1: Enter the chemical name "Salbutamol" to generate the structure from the name 2: Click on "Submit" to create the structure Worked Example: Create Salbutamol Query

The chemical structure has been created from the name "Salbutamol". Chemists could also draw this structure by hand. 2.Define the structure as „Product“ and remove salts, mixtures, etc. from the hitset by checking boxes 3.Click " Save Query" to save the structure, if you want to re-use the structure drawing in a seperate session via " Load Query" 4.Click on " Search" to start the search 3): Query is Ready.. Query is ready…

1 1: Click on "View Results" to see the preparations of this compound Search is complete…

1.There are many preparations (51) spread over many documents (38). Reaxys gives you unique methods of providing an overview. 1.First select a multi-step view (e.g. 5 steps) and click "Limit to" 1 2 Prepare to zoom back

1 2 Prepare to Zoom In 1.You immediately see a route starting from salicyl aldehyde. 2.To create a synthesis plan for the entire process, click on the "Context" button of the product and select "Plan a Synthesis"

1.An overview of the entire synthesis including conditions for each of the steps 2.Each step gives you the chance to find a better way of making each intermdiate, by clicking "Modify" 3.Information on where to buy it! Zoom IN

1 1: Select Substance and Properties" to search a substance with all its data. 2: Click "Search" 2 Worked Example: Substance Properties

3): Zoom IN: Property Overview (e.g. pK)

2 1.5 Hits: Salbutamol and its stereo-isomers 2.Physical, spectral, bioactivity, application data 3.Zoom IN on R-Salbutamol synthesis by clicking on "6 prep" 3 1 Zoom Back: Substance Overview

1.Asymmetric catalysis details 2.Click on "Scopus" for "cited-by" info for this article or on "Full Text" for PDF from ScienceDirect 3.Also patent data Zoom IN: Source Document (e.g. Journal)

Zoom IN to Scopus: Other Relevant Papers

Zoom IN to Scopus: Review Articles

Zoom In: Source Document - Patent Experimental reaction procedure extracted from the patent 2.Abstract of this patent document 3.Click on "Full Text" to link to the EspaceNet-patent server 3

3 1.Browse down to see substance 8 2.Click on "Spectra" and on "IR Spectroscopy" to see the IR peaks (finger-print data) used for identification of the product 1 2 Zoom IN: Property Data for R-Salbutamol

Coming soon: Zoom IN for Structure/Property Space Salbutamol Ephedrine Isoprenaline Adrenaline Bronchodilator action (anti-asthma)

Type "adrenaline" 2.Set "Substructure" 3.Specify "LD50" Coming soon: Zoom IN for Structure/Property Space

1.Click "Hit Data" for LD50 values 1 1 Coming soon: Zoom IN for Structure/Property Space

1% 3000% of adrenaline toxicity (mice) 2000 % Coming soon: Zoom IN for Structure/Property Space

In this example you have seen: How can Salbutamol be synthesized? Process details? Yields? Patents? How to buy or synthesize the starting materials? Supplier data? Reactions? Are there spectral or physical data to identify the compound? Which physical, bioactivity and application data does it have? Which key publications should I read? (Where is it placed in Structure/Property/Reaction Space?)

31 4. Summary

32 4. Summary Reaxys – designed by chemists for chemists. Use Reaxys workflow solutions to get the relevant results instantly Use the functionalities and go beyond data searching: results exporting and management, analysis tools, workflow solution Synthesis planner: Plan multi-step synthesis, compare alternative synthetic routes. Make quick decision on the most appropriate pathway Short cuts to structures, broaden and narrowing searches by changing structure constrains and using filtering and analysis tools Instant access to reliable experimental data including the properties of substance, spectroscopic data, experimental procedures.

Direct positive feedback from the global user community

 Additional content: Patent Chemistry Database (PCD) --- patent documents from  Harmonised content of Beilstein, Gmelin and PCD --- extensive repository of chemical properties and reaction data presented with chemistry as the organizing principle.  Innovative workflow tool with simple interface and new powerful analysis and planning tools to that help to plan the synthesis of target compounds efficiently  Web-based, no installation efforts required. Simply access at  Continuous updated product with no service interruption to consortium members.  Elsevier now provides technical & scientific and phone support with Chinese speaking product specialists Benefits of migration to Reaxys

24 Hour user support 24-hour helpdesk (Ph.D Chemists answer your questions: – 3 – (reads and writes Chinese) Self-pace Training Center:

We would like to hear what you think …so that we can best align and serve your needs. You are welcome to contact us if there are questions: Doreen Tan 陈慧敏 Senior Product Sales Manager, Life Science Dr. Ping Yin 尹平 Reaxys Trainer 培训讲师

谢谢！ Thank you for coming to the on-site training session …and for your patient attention

38 Trademark statement: All products mentioned are trademarks owned by Elsevier Forward-looking-statement-disclaimer: This presentation contains forward-looking statements and information – that is, statements related to future, not past, events. These statements may be identified by words such as "expects," "looks forward to," "anticipates," "intends," "plans," "believes," "seeks," "estimates," "will," "project" or words of similar meaning. Such statements are based on our current expectations and certain assumptions, and are, therefore, subject to certain risks and uncertainties