Methyl 14-ethylidene-18-oxa-2,12-diazahexacyclo[9.6.1.19,15.01,9.03,8.012,17]nonadeca-3,5,7-triene-19-carboxylate

Base Information

• Chemical Name: Methyl 14-ethylidene-18-oxa-2,12-diazahexacyclo[9.6.1.19,15.01,9.03,8.012,17]nonadeca-3,5,7-triene-19-carboxylate
• CAS No.: 4684-32-6
• Molecular Formula: C₂₀H₂₂N₂O₃
• Molecular Weight: 338.406
• DSSTox Substance ID: DTXSID30425161
• Wikipedia: Picrinine
• Wikidata: Q72499464,Q105100575
• Mol file: 4684-32-6.mol

Synonyms:picrinine

Chemical Property of Methyl 14-ethylidene-18-oxa-2,12-diazahexacyclo[9.6.1.19,15.01,9.03,8.012,17]nonadeca-3,5,7-triene-19-carboxylate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 222-224 °C
• Boiling Point: 501.1°Cat760mmHg
• PKA: 4.47±0.40(Predicted)
• Flash Point: 256.9°C
• PSA: 50.80000
• Density: 1.38g/cm³
• LogP: 2.32170
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 338.16304257
• Heavy Atom Count: 25
• Complexity: 678

Purity/Quality:

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

Picrinine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC=C1CN2C3CC1C(C45C3(NC6=CC=CC=C64)OC2C5)C(=O)OC
• Description: An Alstonia alkaloid obtained from A. scholaris R. Br., this base also occurs in Rauwolfia vornitora. It has [α]D - 47° (CHCI3). The ultraviolet spectrum in neutral solution (EtOH) has absorption maxima at 237 and 287 mil, while in acidic solution (perchloric acid), there are absorption maxima at 239, 244 and 305 mil. A methoxycarbonyl group, an alkyl group and an ether bridge are present in the molecule. The picrate is obtained as light yellow crystals with m.p. 172- 4°C (dec.) and the methiodide has m.p. 235-7°C.
• Uses: Picrinine is a monoterpenoid indole alkaloid extracted from Ochrosia elliptica, displaing the enhancement of immunomodulatory activity and apaptosis inducing in the A549 cell lines.

Technology Process of Methyl 14-ethylidene-18-oxa-2,12-diazahexacyclo[9.6.1.19,15.01,9.03,8.012,17]nonadeca-3,5,7-triene-19-carboxylate

There total 36 articles about Methyl 14-ethylidene-18-oxa-2,12-diazahexacyclo[9.6.1.19,15.01,9.03,8.012,17]nonadeca-3,5,7-triene-19-carboxylate 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: 76.0%

(-)-scholarisine C → picrinine (4684-32-6)

Guidance literature:

With pyridinium p-toluenesulfonate; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1021/acs.orglett.1c02393

Reference yield: 75.0%

C26H27N3O8S → picrinine (4684-32-6)

Guidance literature:

With caesium carbonate; In acetonitrile; at 65 ℃; for 1h; Inert atmosphere;

DOI:10.1021/ja501780w

Reference yield: 41.0%

C27H34N2O7 → (-)-scholarisine C + picrinine (4684-32-6)

Guidance literature:

With methanol; acetyl chloride; at 0 - 20 ℃; for 24.5h;

DOI:10.1021/acs.orglett.1c02393

Downstream raw materials:

strictamine

Refernces

• 1、 Smith, Joel M.,Moreno, Jesus,Boal, Ben W.,Garg, Neil K.. "Total synthesis of the akuammiline alkaloid picrinine". . p. 4504 - 4507. Retrieved 2014/04/17.