{

"source": "ORD Dataset Wishlist",

"snapshot_date": "2026-09-25",

"ord_wishlist_status_at_snapshot": "Available",

"ord_wishlist_card": "https://github.com/orgs/open-reaction-database/projects/11?pane=issue&itemId=126570106",

"ord_data_issue": null,

"title": "Generation of multimillion chemical space based on the parallel Groebke–Blackburn–Bienaymé reaction",

"doi": "10.3762/bjoc.20.143",

"journal": "BJOC",

"publication_date": "2024-07-16",

"authors": [

"E.V. Govor",

"Vasyl Naumchyk",

"Ihor Nestorak",

"Dmytro S. Radchenko",

"Dmytro Dudenko",

"Yurii S. Moroz",

"Olexiy D Kachkovsky",

"Oleksandr O. Grygorenko"

],

"article_open_access": {

"status": "diamond",

"license": "cc-by"

},

"dataset_size_estimate": 2000,

"experiment_type": "Parallel synthesis",

"ord_priority": "High",

"ord_difficulty": "Normal",

"source_data_kind": "si_pdf_tables",

"smiles_in_source": "yes",

"needs_author_contact": false,

"data_locations": [

{

"url": "https://www.beilstein-journals.org/bjoc/articles/20/143",

"what": "Article landing page listing SI Files 1-4 (S1 ZIP 6.9 MB, S2 PDF 625 KB, S3 PDF 1.0 MB, S4 PDF 3.0 MB)",

"license": "CC-BY 4.0 (Crossref VOR/AM/TDM; diamond OA)"

},

{

"url": "https://www.beilstein-journals.org/bjoc/content/supplementary/1860-5397-20-143-S2.pdf",

"what": "SI File 2: 'Parallel synthesis of compound library 4'. 169-page text PDF table with columns #, ID, product structure as CXSMILES, internal ID, amine/aldehyde/isonitrile IDs and SMILES, yield (mg and %). About 2052 rows, grouped into condition sections (e.g. preliminary TsOH vs Sc(OTf)3 catalyst runs)",

"license": "CC-BY 4.0 (stated in the SI file header)"

},

{

"url": "https://www.beilstein-journals.org/bjoc/content/supplementary/1860-5397-20-143-S1.zip",

"what": "SI File 1: ZIP of 3 PDFs of drawn reactant structures (amines 1, aldehydes 2, isonitriles 3)",

"license": "CC-BY 4.0"

},

{

"url": "https://www.beilstein-journals.org/bjoc/content/supplementary/1860-5397-20-143-S3.pdf",

"what": "SI File 3: experimental part (general procedures and conditions, characterization)",

"license": "CC-BY 4.0"

}

],

"notes": "Parallel Groebke-Blackburn-Bienaymé 3-component library synthesis (Enamine), about 700 unique products. The data is in SI File 2, a text-based PDF table (CC-BY 4.0). Each row gives the product SMILES (ChemAxon CXSMILES with |c:...,t:...| extensions), the amine, aldehyde and isonitrile IDs and SMILES, and the yield in mg and %. There are about 2052 rows, including zero-yield outcomes, which should be kept as negative results. General procedures and conditions are in SI File 3. Reactant structure drawings are in SI File 1 (ZIP of PDFs). Pitfalls: long SMILES wrap across several text lines inside table cells, so parse by column position (e.g. pdfplumber word coordinates) rather than by raw text order. Strip CXSMILES extensions before validation. Amines may appear as salts (e.g. 'Cl.' prefix). Rows are grouped under condition headings (preliminary experiments with TsOH vs Sc(OTf)3 catalyst, then the library runs), and those conditions must be carried into each reaction. An author-supplied spreadsheet version is reported to exist but is not public. Check with the ORD maintainers before starting to avoid duplicated effort. Cite DOI 10.3762/bjoc.20.143.",

"verification_caveats": "Rows run across many condition sections (catalyst and scale vary), so templating must track section headers. Wrapped SMILES make reconstruction errors likely, which can be checked with RDKit parse plus a GBB reaction template (amine + aldehyde + isonitrile -> product) against the listed product SMILES. Yields are isolated mg/%; confirm purification and analysis details in SI File 3. The 2052 rows exceed ORD's estimate of 2000; reconcile the count."

}