Solving Tough Chemistry Problems Using Reaxys

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WEBINAR:SEARCHING FOR

CHEMICAL REACTION

INFORMATION ON REAXYS

SEPTEMBER 16, 2014

Chris Flemming Damon Ridley

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THE CHALLENGES

1. There are many ways to describe chemical reactions, e.g.:

1. By specific structure queries

2. By type of transformation (e.g., functional groups)

3. By named reactions

2. There are many issues relating to the entry of information in databases, e.g.:

a. Every reaction?

b. Multi or single step reactions?

c. Stages in a single reaction?

d. General Procedures?

3. There are many ways to search for chemical reactions, e.g.:

a. Through reaction diagrams

b. From substances

c. By keywords

d. Named Reactions

e. Types of reactions

f. Reaction conditions

i. Yields

ii. Solvents

iii. Catalysts

SEARCHING FOR CHEMICAL REACTIONS

AUTHORS

DATABASE

PRODUCERS

SEARCHERS

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Substances

Substance Database

Title and Abstract

Bibliographic Database

Reactions

Reaction Database

ORIGINAL DOCUMENTS: JOURNAL ARTICLES AND PATENTS

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A Record in a BIBLIOGRAPHIC DATABASE

The record is for a single article

Title, Abstract, Keywords (from different sources), and Substances and Reactions from this original document

are shown here

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A Record in a SUBSTANCE DATABASE

The record is for a single

substance

This information comes from many

different documents

Links to Chemical Reaction

Information

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A Record in a REACTION DATABASE

The record is for a single

reaction

This information comes from different

documents

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Q: WHICH DATABASE DO I USE?

A: Know your options!

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OPTIONS TO SEARCH FOR REACTION INFORMATION IN REAXYS

Reaction QUERYLETS

Our main choices for searching reaction information in Reaxys

1. Ask Reaxys - “an intelligent Google-like experience”

2. Reactions Form- reaction structure queries and reaction data

3. Substances Form- find substance then look for preparations/ reactions in the substance record

4. Literature Form- search by keywords

5. ReaxysTree

- browse and search reaction hierarchies

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Poll Question 1

To find preparations for ritalin, what would be your first choice?

1. Ask Reaxys

- “an intelligent Google-like experience”

2. Reactions Form

- reaction structure search and reaction data search

3. Substances Form

- find substance then look for preparations/reactions in the substance record

4. Literature Form

- search by keywords

5. ReaxysTree

- browse and search reaction hierarchies

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DAMON’S CHOICE

Ask Reaxys – “an intelligent Google-like experience”

BY FAR!!!!!!

To find preparations for ritalin, what would be my first choice?

FOR THIS TYPE OF QUESTION….

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ONE CLICK…

… to Answers

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Synthesis PlannerA chemist draws a synthetic route from A to B to C:

CBA

Reagent(s)

Reagent(s)

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Synthesis PlannerA chemist draws a synthetic route from A to B to C:

CBA

Reagent(s)

Reagent(s)

Synthesis Planner works the other way

A1

A2Synthesi

ze

Detail(s)

Detail(s)

C

B1

B2

B3

Synthesize

SYNTHESIS 3

SYNTHESIS 2

SYNTHESIS 1

Synthesize

Detail(s)

Detail(s)

Detail(s)

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Synthesis PlannerA chemist draws a synthetic route from A to B to C:

CBA

Reagent(s)

Reagent(s)

Synthesis Planner works the other way

A1

A2Synthesi

ze

Detail(s)

Detail(s)

Help messages in the Synthesis Planner indicate how to Add or Remove branches, and how to perform other operations

We may repeat the process backwards if we wish

C

B1

B2

B3

Synthesize

SYNTHESIS 3

SYNTHESIS 2

SYNTHESIS 1

Synthesize

Detail(s)

Detail(s)

Detail(s)

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Synthesize => SYNTHESIS PLANNER

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Synthesize => SYNTHESIS PLANNER

SYNTHETIC SEQUENCE

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Clicked on last slide

SYNTHETIC SEQUENCE

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Clicked on last slide

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A COMPARISON

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citations

citations

reactions

Ask Reaxys ABOUT THE MITSUNOBU REACTION

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citations

citations

reactions

Ask Reaxys ABOUT THE MITSUNOBU REACTION

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Reaction Sort

Options

Ask Reaxys about THE MITSUNOBU REACTION

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Ask Reaxys about THE MECHANISM OF THE MITSUNOBU REACTION

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So what do you now think about Ask Reaxys?

o Very interesting and I’ll give it a tryo I hope Reaxys can develop it furthero I’d like another webinar on how to use Ask Reaxys to

solve other questionso Not of interest

You can click more than one option if you like

Poll Question 3

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REACTIONS FORM : STRUCTURE SEARCH

Search reactions by structure is easy.

We can map atoms, specify bonds taking part in the reaction and so forth.

Reactions

Form

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In chemical reaction diagrams, stereochemical elements may be entered into starting materials and products.

REACTIONS FORM : STRUCTURE SEARCH (STEREOCHEMISTRY)

Note that results from different publications

are displayed together

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REACTIONS FORM : REACTION DATA

STRUCTURES

Go here for (reaction) queries by

STRUCTURE

QUERYLETS

Go here for (reaction) queries by

DATA/KEYWORDS

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REACTIONS FORM : REACTION DATA OPTIONS

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WORKING WITH QUERYLETS

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STRUCTURE + QUERYLET SEARCH

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Whoops!

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FILTER BY : SUBSTRUCTURE

Steps:

1. Click Filter by: sub-structure2. Draw structure3. Click Exclude

Step 1

Step 2

Step 3

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That’s Better!

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REACTION TYPE QUERYLET : HETERO DIELS ALDER CYCLIZATIONS

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That’s Better!ANSWERS : HETERO DIELS ALDER CYCLIZATIONS

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CHOICES TO FIND CHEMICAL REACTION INFORMATION IN REAXYS

Our main choices in Reaxys1. Ask Reaxys

- “an intelligent Google-like experience”

2. Reactions Form- reaction structure queries and reaction data

3. Substances Form- find substance then look for preparations/reactions in the substance record

4. Literature Form- search by keywords

5. ReaxysTree- browse and search reaction hierarchies

✔

✔

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SUBSTANCES FORM

All Preparations

All Reactions

Preparations and Reactions

for a single substance

Reaxys has many unique ways to find substances, e.g., through part-names

and part-formulas

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QUERYLETS TO SEARCH FOR SPECIFIC REACTION FIELDS IN SUBSTANCE RECORDS

Catalysts for the Suzuki Reaction

Step 1: Click

Step 5: Type

Step 6: Click

Step 2: Type

Step 4: Add

Step 3: Highlight

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QUERYLETS TO SEARCH FOR SPECIFIC REACTION FIELDS IN SUBSTANCE RECORDS

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LITERATURE FORMS

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LITERATURE FORMS

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LITERATURE FORMS AND Ask Reaxys

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ReaxysTree

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ReaxysTree: MITSUNOBU

Over 1000 references to the specific reaction

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ReaxysTree: WORKING THROUGH HIERARCHIES

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ReaxysTree: WORKING THROUGH HIERARCHIES

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ReaxysTree: Dehydrogenase Reactions

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Ask Reaxys: Dehydrogenase Reaction

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OPTIONS TO SEARCH FOR REACTION INFORMATION IN REAXYS

WHICH ONE?

1. Ask Reaxys (Beta version)- Preparation of ritalin => preparations, citations- Mitsunobu reaction => reactions, citations - Mechanism of the Mitsunobu reaction => citations- Phase transfer catalysis => reactions, citations- Phase transfer catalysts => substances, citations- Dehydrogenase reactions => citations

2. Reactions Form- Similarity search –COOH => -CF3- Stereochemistry search in reaction diagram- Subject Studied (16 terms): kinetics, benzyl halides to benzyl alcohols

(structure)- Reaction Type (>1,000 terms): hetero diels alder cyclizations

3. Substances Form- Catalysts for Suzuki reactions

4. Literature Form- Citation Basic Index: phase NEXT transfer* NEXT catalys*

5. ReaxysTree- Mitsunobu reaction => citations (plus hit reactions)- Dehydrogenase catalysed reactions

KNOW YOUR BASIC OPTIONS

EXPERIMENT

TRY ALTERNATIV

ES

YOU HAVE OPPORTUNITIES

!

and share your

experiences with us

“LOOKUP” & AUTOSUGGES

T

Worth a try for most searches Think about options in

Analysis Table

If first search not “successful”, then think why, and try something simpler?

Structure search for reactions

There are ~ 20 different reaction querylets Subject Studied and

Reaction Type provide valuable options to focus search

There are ~ 20 different ways to search for substances

(Sub)Structure, (Part)Name and (Part)Formula search for substances, Substance Querylets WEBINAR?

“In depth keyword searches” in >48 million records

Thousands of options under “chemical transformations”

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Share your innovative Reaxys searches with Damon

Send email to: bdtraining@elsevier.com

REQUEST