Austrobailignan 1

Base Information

• Chemical Name: Austrobailignan 1
• CAS No.: 55955-07-2
• Molecular Formula: C₂₁H₁₈O₇
• Molecular Weight: 382.37
• NSC Number: 294826
• DSSTox Substance ID: DTXSID001105675
• Nikkaji Number: J11.089B
• Wikidata: Q27105888
• Metabolomics Workbench ID: 68459
• ChEMBL ID: CHEMBL509850
• Mol file: 55955-07-2.mol

Synonyms:austrobai-lignan-1;austrobailignan 1;austrobailignan-1

Chemical Property of Austrobailignan 1

Chemical Property:

• Boiling Point: 568.8°Cat760mmHg
• Flash Point: 251.2°C
• Density: 1.423g/cm³
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 382.10525291
• Heavy Atom Count: 28
• Complexity: 626

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=CC2=C1OCO2)C3C4C(CC5=CC6=C(C=C35)OCO6)COC4=O
• Isomeric SMILES: COC1=CC(=CC2=C1OCO2)[C@H]3[C@@H]4[C@@H](CC5=CC6=C(C=C35)OCO6)COC4=O

Technology Process of Austrobailignan 1

There total 2 articles about Austrobailignan 1 which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 40.0%

(-)-5''-Methoxyhinokinin (112448-63-2) → (-)-austrobailignan 1 (55955-07-2)

Guidance literature:

With ferrous(II) sulfate heptahydrate; ATGGGCAGCACCGCGCCGCTGCGTTTCCCGGTTATCGATTTGAGCATGAAGAACCTGAAACCTGGAACCACATCATGGAACAGCGTACGCACTCAGGTGCGTGAAGCTTTGGAAGAATATGGTTGCTTTGAAGCCGTTATTGATGCGGTTTCCCCAGAGTTGCAAAAAGCTGTCTGCAACAAGGGGCACGAACTGTTAAATTTACCGCTGGAGACCAAGATGCTTAATGGTAATAAGCCGGAGTACGATGGATTTACATCAATCCCGAACCTTAACGAAGGTATGGGTGTTGGCCGCATCACTGACTTAGAGAAGGTCGAACGTTTCACTAATCTGATGTGGCCTGAGGGGAACAAGGATTTTTGCGAAACAGTTTACTCCTATGGTAAGCGCATGGCAGAGGTTGACCATATTCTGAAGATGATGGTATTCGAATCTTTTGGTATGGAGAAACATTTTGACTCCTTCTGCGAAAGTACAAATTACTTGCTGCATTTCATGCGCTATCAACAACCCGGCAAAGACGGTCGCTCTCCCGCATTGAGTTTACACAAAGATAAATCTATCCTTACGATCGTCAACCAAAACGATGTAAAAGGACTGGAGTTCGAAACAAAGGATGGCGAATGGATTTTGCCAACAGCCGATAACCACATCGTATTACTTGGAGATTGCTTCATGGCTTGGAGTAACGGTCGCCTGCACTCTCCACTGCACCGTGTGACATTAGTGGCAAATCAGGCACGTTTGAGTACCTCCTCATTTAGCTTCCCAAAAGATATTATTGAGACACCGGCGGAATTGGTGGACGAGGAACATCCGCTTTTATTCAATCCCTTCGAGATCACCGAGCTTTTAGCCTACTGTTTTACAAAAGAAGGAGCCAAGGCGGTTTGCGATTTAAAGCAGTATAAAGCGTACACTGGAGCATGA; α-ketoglutaric acid disodium salt; ascorbic acid; In dimethyl sulfoxide; at 23 ℃; for 20h;

DOI:10.1002/anie.201904102

Reference yield:

(R)-(+)-3-piperonyl-4-butanolide (17187-77-8) + 3-methoxy-4,5-methylenedioxybenzyl bromide (108853-31-2) → (-)-austrobailignan 1 (55955-07-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C

1.2: 2 h

2.1: ascorbic acid; α-ketoglutaric acid disodium salt; ferrous(II) sulfate heptahydrate; ATGGGCAGCACCGCGCCGCTGCGTTTCCCGGTTATCGATTTGAGCATGAAGAACCTGAAACCTGGAACCACATCATGGAACAGCGTACGCACTCAGGTGCGTGAAGCTTTGGAAGAATATGGTTGCTTTGAAGCCGTTATTGATGCGGTTTCCCCAGAGTTGCAAAAAGCTGTCTGCAACAAGGGGCACGAACTGTTAAATTTACCGCTGGAGACCAAGATGCTTAATGGTAATAAGCCGGAGTACGATGGATTTACATCAATCCCGAACCTTAACGAAGGTATGGGTGTTGGCCGCATCACTGACTTAGAGAAGGTCGAACGTTTCACTAATCTGATGTGGCCTGAGGGGAACAAGGATTTTTGCGAAACAGTTTACTCCTATGGTAAGCGCATGGCAGAGGTTGACCATATTCTGAAGATGATGGTATTCGAATCTTTTGGTATGGAGAAACATTTTGACTCCTTCTGCGAAAGTACAAATTACTTGCTGCATTTCATGCGCTATCAACAACCCGGCAAAGACGGTCGCTCTCCCGCATTGAGTTTACACAAAGATAAATCTATCCTTACGATCGTCAACCAAAACGATGTAAAAGGACTGGAGTTCGAAACAAAGGATGGCGAATGGATTTTGCCAACAGCCGATAACCACATCGTATTACTTGGAGATTGCTTCATGGCTTGGAGTAACGGTCGCCTGCACTCTCCACTGCACCGTGTGACATTAGTGGCAAATCAGGCACGTTTGAGTACCTCCTCATTTAGCTTCCCAAAAGATATTATTGAGACACCGGCGGAATTGGTGGACGAGGAACATCCGCTTTTATTCAATCCCTTCGAGATCACCGAGCTTTTAGCCTACTGTTTTACAAAAGAAGGAGCCAAGGCGGTTTGCGATTTAAAGCAGTATAAAGCGTACACTGGAGCATGA / dimethyl sulfoxide / 20 h / 23 °C

With ferrous(II) sulfate heptahydrate; ATGGGCAGCACCGCGCCGCTGCGTTTCCCGGTTATCGATTTGAGCATGAAGAACCTGAAACCTGGAACCACATCATGGAACAGCGTACGCACTCAGGTGCGTGAAGCTTTGGAAGAATATGGTTGCTTTGAAGCCGTTATTGATGCGGTTTCCCCAGAGTTGCAAAAAGCTGTCTGCAACAAGGGGCACGAACTGTTAAATTTACCGCTGGAGACCAAGATGCTTAATGGTAATAAGCCGGAGTACGATGGATTTACATCAATCCCGAACCTTAACGAAGGTATGGGTGTTGGCCGCATCACTGACTTAGAGAAGGTCGAACGTTTCACTAATCTGATGTGGCCTGAGGGGAACAAGGATTTTTGCGAAACAGTTTACTCCTATGGTAAGCGCATGGCAGAGGTTGACCATATTCTGAAGATGATGGTATTCGAATCTTTTGGTATGGAGAAACATTTTGACTCCTTCTGCGAAAGTACAAATTACTTGCTGCATTTCATGCGCTATCAACAACCCGGCAAAGACGGTCGCTCTCCCGCATTGAGTTTACACAAAGATAAATCTATCCTTACGATCGTCAACCAAAACGATGTAAAAGGACTGGAGTTCGAAACAAAGGATGGCGAATGGATTTTGCCAACAGCCGATAACCACATCGTATTACTTGGAGATTGCTTCATGGCTTGGAGTAACGGTCGCCTGCACTCTCCACTGCACCGTGTGACATTAGTGGCAAATCAGGCACGTTTGAGTACCTCCTCATTTAGCTTCCCAAAAGATATTATTGAGACACCGGCGGAATTGGTGGACGAGGAACATCCGCTTTTATTCAATCCCTTCGAGATCACCGAGCTTTTAGCCTACTGTTTTACAAAAGAAGGAGCCAAGGCGGTTTGCGATTTAAAGCAGTATAAAGCGTACACTGGAGCATGA; α-ketoglutaric acid disodium salt; lithium hexamethyldisilazane; ascorbic acid; In tetrahydrofuran; dimethyl sulfoxide;

DOI:10.1002/anie.201904102

upstream raw materials:

(-)-5''-Methoxyhinokinin

(R)-(+)-3-piperonyl-4-butanolide

3-methoxy-4,5-methylenedioxybenzyl bromide