The long and winding road to chemical information
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Transcript of The long and winding road to chemical information
The Long and Winding Road toChemical Information
Engelbert Zass (retd.)
Chemistry Biology PharmacyInformation Center
ETH Zurich
8093 Zürich, Switzerland
Dedicated to the Memory of
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Dr. Ursula Schoch-Grübler Prof. Dr. Reiner Luckenbach1949 – 2011 1941 – 2011
Beilstein ⇒ Reaxys
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Beilstein: Handbook ⇐ Excerption
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Beilstein: Handbook ⇒ Database
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1994
2009
1988
1991
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The Long and Winding Road to
Chemical Information
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Robert Burns
Woodward
1917-1979
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330 publications,including 100 patents
3rd Europ. Symp. Vitamin B12 and Intrinsic Factor
Zürich, March 1979
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Vitamin B12
Total Synthesis:
R.B. Woodward
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Heterocycles 82, 63-86 (2010)
Publications by A. Eschenmoser
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SciFinder: Molecular Formula
• Manganese(II)sulfate
MnO4S ⇒ H2O4S . Mn
• Iron(II)formiate
CHFeO2 ⇒ CH2O2 . ½ Fe
• Berylliumphosphate
Be3O8P2 ⇒ Be . 2/3 H3O4P
but:
• Sodium ClorideCl Na (Cl . Na gives different result)
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Ca3(PO4)2 • 3 H2O
SciFinder: Claims and Hype
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Essentially correct and true (relatively speaking)
Hype and dangerous insinuation !
SciFinder: Preparation of a Compound
• Search via:
1. Get Reaction: Product
(CASREACT)
2. Additional Reactions
(CASREACT ⇒ CAplus)
3. Registry Role Matrix (Patents, Nonpatents)
(Registry ⇒ CAplus)
4. Get References – Limit results to: Preparation
(CAplus)
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Preparation of Lidocaine (27.6.2009)
• Reaxys
23 refs. 1946-2008
• SciFinder Web
– CASREACT: 4 refs. 1984-2009
– CAplus: 109 refs. 1948-2009
only 45 relevant !
CHMINF-L
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Steroids with Data in Literature
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all carbon skeleton, any bonds, any substitution, no anellated rings
Properties: Data, Spectra
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SciFinder:
Dipole Moments for
Aminoquinolines
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Reaxys:
Dipole Moments for
Aminoquinolines
Dipole Moments of
Aminoquinolines and Aminoacridines
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cis-Hydroxylation: SciFinder / Reaxys
Reagenz Reaxys SciFinder
H2O2 / Molybdenum tungsten hydroxide oxide phosphate 7
H2O2 / Tricarbonyl(η5-cyclopentadienyl)(phenylethynyl)molybdenum 1
H2O2 / fac-Trichloro(1,4,7-trimethyl-1,4,7-triazacyclononane)ruthenium 1
H2O2 / Ruthenium(1+), aqua(octahydro-1,4,7-trimethyl-1H-1,4,7-triazonine-
κN1,κN4,κN7)bis(2,2,2-trifluoroacetato-κO)-, (OC-6-33)-, 2,2,2-trifluoroacetate (1:1)
1 3
H2O2 1 1
B2Cl4 / H2O2 1
H2O2 / Tris-µ-oxobis[(1,4,7-trimethyl-1,4,7-triazacyclononane)manganese(IV)]
hexafluorophosphate
1 1
KMnO4 10 1
Methyltriphenylphosphonium permanganate 1
N-methylmorpholineoxide / OsO4 1 2
K2OsO4 / OsO4 1
K3Fe(CN)6 / K2OsO4 1 1
I2 / AgOAc 1 1
cis-Hydroxylation: SciFinder
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Chemical Information: State of the Art
• Neither «new» nor «old» sources arecomprehensible or reliable enoughon an individual basis
⇒ one source is usually not enough !
• The traditional strenght of «old» sourcesis partially negated by the complexity oftheir content (data structure)
⇒ improve databases (not only interfaces)
Improve Education & Support
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The Past: "Must Use" Brands
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Present: Many "Equal" Brands
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Dendrobine Total Syntheses (4/2012)
• Total relevant references: 43 (1965-2012)
– SciFinder 38 of 54 (10 excl.)
– Reaxys 13 of 14 (none excl.)
– Web of Knowledge 20 of 22 (none excl.)
– Scopus 18 of 19 (none excl.)
– Google Scholar 18 of 18 (1 excl.: grant)
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Databases: Problems and Dangers
2°Literature (A&I, Handbooks) =endangered species ?
• (Relatively) complex interfaces
• Too many sources needed
• Too many differences between sources
• Problematic legacies
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(Cost) Effort / Utility ratio not obvious enough
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Remedies
• To Producers & Specialists:
– Meta Data about Sources
– Exchange & Feedback of Experience
• To Users:
– Support
– Education & Training
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Meta Data: Gmelin, CASREACT
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