CID 31306

Base Information

• Chemical Name: CID 31306
• CAS No.: 17617-45-7
• Molecular Formula: C15H16 O6
• Molecular Weight: 292.31
• European Community (EC) Number: 634-009-1
• NCI Thesaurus Code: C87770
• Mol file: 17617-45-7.mol

Synonyms:picrotoxinin;picrotoxinine

Chemical Property of CID 31306

Chemical Property:

• Vapor Pressure: 1.82E-14mmHg at 25°C
• Melting Point: 203-205°C
• Refractive Index: 1.4359 (estimate)
• Boiling Point: 551.6°Cat760mmHg
• PKA: 13.18±0.60(Predicted)
• Flash Point: 214°C
• PSA: 85.36000
• Density: 1.52g/cm³
• LogP: -0.06200
• Storage Temp.: 2-8°C
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 292.09468823
• Heavy Atom Count: 21
• Complexity: 642

Purity/Quality:

98%,99%, ^*data from raw suppliers

Picrotoxinin ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T+
• Statements: 25-28
• Safety Statements: 13-20-45-36/37-28

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=C)C1C2C3C4(C(C1C(=O)O2)(CC5C4(O5)C(=O)O3)O)C
• Isomeric SMILES: CC(=C)[C@@H]1C2[C@@H]3[C@@]4([C@](C1C(=O)O2)(CC5[C@]4(O5)C(=O)O3)O)C

Technology Process of CID 31306

There total 72 articles about CID 31306 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: 100.0%

(-)-Bromopicrotoxinin (20744-71-2) → picrotoxinin (17617-45-7)

Guidance literature:

With copper; ammonium chloride; zinc; In ethanol; for 0.5h; Heating;

DOI:10.1021/ja00192a035

Reference yield: 99.0%

β-Brom-picrotoxinin (20744-71-2) → (-)-picrotoxinin (17617-45-7)

Guidance literature:

With ammonium chloride; zinc; In ethanol; for 1h; Heating;

DOI:10.1021/ja00328a041

Reference yield: 96.0%

β-Brom-picrotoxinin (20744-71-2) → picrotoxinin (17617-45-7)

Guidance literature:

With ammonium chloride; zinc; In ethanol; water; at 95 ℃; for 2h; Inert atmosphere;

DOI:10.1021/jacs.0c05042

upstream raw materials:

(2aS)-2a,3c-epoxy-4a-hydroxy-9syn-(α-hydroxy-isopropyl)-8b-methyl-(2ar,4ac,8ac,8bc)-octahydro-1,7-dioxa-5c,8c-methano-cyclopent[cd]azulene-2,6-dione; compound with picrotoxinin

(-)-Bromopicrotoxinin

8,9-deoxypicrotoxinin

(1R,3R,5S,8R,9S,11R)-9-(bromomethyl)-5,9-dimethyl-3-hydroxy-11-(hydroxymethyl)-4-methylidine-10-oxotricyclo<6.2.1.0^1.5>undec-6-ene

Downstream raw materials:

13-(Phenylseleno)picrotin

picrotin

α-dihydropicrotoxinin

(2aS)-9syn-acetyl-2a,3c-epoxy-4a-hydroxy-8b-methyl-(2ar,4ac,8ac,8bc)-octahydro-1,7-dioxa-5c,8c-methano-cyclopent[cd]azulene-2,6-dione

Refernces

• 1、 Burdge, Hannah E.,Crossley, Steven W. M.,Lambrecht, Michael J.,Shenvi, Ryan A.,Tong, Guanghu. "Synthesis of (-)-Picrotoxinin by Late-Stage Strong Bond Activation". . . Retrieved 2020.
• 2、 Trost, Barry,Krische, Michael J.. "Palladium-catalyzed enyne cycloisomerization reaction in an asymmetric approach to the picrotoxane sesquiterpenes. 2. Second-generation total syntheses of corianin, picrotoxinin, picrotin, and methyl picrotoxate". . p. 6131 - 6141. Retrieved 2007/10/03.