Corianin

Base Information

• Chemical Name: Corianin
• CAS No.: 35481-77-7
• Molecular Formula: C15H18O6
• Molecular Weight: 294.2998
• Nikkaji Number: J3.546.718A
• Wikidata: Q105114939
• Mol file: 35481-77-7.mol

Synonyms:corianin

Chemical Property of Corianin

Chemical Property:

• Vapor Pressure: 5.54E-14mmHg at 25°C
• Melting Point: 216-217 °C
• Boiling Point: 541.5°Cat760mmHg
• PKA: 12.75±0.70(Predicted)
• Flash Point: 208.7°C
• PSA: 88.52000
• Density: 1.583g/cm³
• LogP: -0.61780
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 294.11033829
• Heavy Atom Count: 21
• Complexity: 603

Purity/Quality:

98%min ^*data from raw suppliers

Corianin 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=C)C1C2C3C4(C(CO3)(C5C(C4(C1C(=O)O2)O)O5)O)C
• Isomeric SMILES: CC(=C)[C@@H]1[C@@H]2[C@@H]3[C@]4([C@@](CO3)([C@H]5[C@@H]([C@]4([C@H]1C(=O)O2)O)O5)O)C

Technology Process of Corianin

There total 71 articles about Corianin 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: 87.0%

C15H18O5 (172172-92-8) → corianine (35481-77-7)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 ℃;

DOI:10.1021/ja953060r DOI:10.1016/S0040-4020(98)00350-0 DOI:10.1021/ja990183t

Reference yield:

C15H16O6 (172172-89-3) → corianine (35481-77-7)

Guidance literature:

Multi-step reaction with 4 steps

1: LiBH₄, AcOH / tetrahydrofuran / 0.5 h / 0 °C

2: 98 percent / Me₃SiCl, 20 h / acetonitrile / 20 h / Ambient temperature

3: 84 percent / Ph₃SnH, AIBN / toluene / 1.5 h / Heating

4: 87 percent / MCPBA / CH₂Cl₂ / 0 °C

With lithium borohydride; chloro-trimethyl-silane; 2,2'-azobis(isobutyronitrile); triphenylstannane; acetic acid; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; toluene; acetonitrile;

DOI:10.1021/ja990183t

Reference yield:

8,9-dihydroxypicrotoxinin (172172-87-1) → corianine (35481-77-7)

Guidance literature:

Multi-step reaction with 5 steps

1: N-methylimidazole, triflic anhydride / 1 h / 100 °C

2: LiBH₄, AcOH / tetrahydrofuran / 0.5 h / 0 °C

3: 98 percent / Me₃SiCl, 20 h / acetonitrile / 20 h / Ambient temperature

4: 84 percent / Ph₃SnH, AIBN / toluene / 1.5 h / Heating

5: 87 percent / MCPBA / CH₂Cl₂ / 0 °C

With 1-methyl-1H-imidazole; lithium borohydride; chloro-trimethyl-silane; 2,2'-azobis(isobutyronitrile); trifluoromethylsulfonic anhydride; triphenylstannane; acetic acid; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; toluene; acetonitrile;

DOI:10.1021/ja990183t

upstream raw materials:

C₁₅H₁₈O₅

C₁₉H₂₆O₇

(3aR,3bR,6R,7S,7aR,8aR)-3a-Benzyloxymethyl-7a-hydroxy-6-isopropenyl-2,2,3b-trimethyl-3b,6,7,7a,8,8a-hexahydro-3aH-indeno[1,2-d][1,3]dioxole-7-carbaldehyde

C₁₉H₂₈O₇

Downstream raw materials:

acetylcorianin

Refernces

• 1、 Trost, Barry M.,Haffner, Curt D.,Jebaratnam, David J.,Krische, Michael J.,Thomas, Andrew P.. "The palladium-catalyzed enyne cycloisomerization reaction in a general approach to the asymmetric syntheses of the picrotoxane sesquiterpenes. Part I. First-generation total synthesis of corianin and formal syntheses of picrotoxinin and picrotin". . p. 6183 - 6192. Retrieved 2007/10/03.
• 2、 Trost, Barry M.,Krische, Michael J.. "General strategy for the asymmetric synthesis of the picrotoxanes". . p. 233 - 234. Retrieved 2007/10/03.