Tubotaiwine

Base Information

• Chemical Name: Tubotaiwine
• CAS No.: 6711-69-9
• Molecular Formula: C₂₀H₂₄N₂O₂
• Molecular Weight: 324.423
• ChEMBL ID: CHEMBL508920
• Metabolomics Workbench ID: 140691
• Wikidata: Q27138847
• Mol file: 6711-69-9.mol

Synonyms:condyfolan-16-carboxylic acid, 2,16-didehydro-, methyl ester;dihydrocondylocarpine;tubotaiwin;tubotaiwine

Chemical Property of Tubotaiwine

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 467.687°C at 760 mmHg
• Flash Point: 236.649°C
• PSA: 41.57000
• Density: 1.267g/cm³
• LogP: 2.98690
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 324.183778013
• Heavy Atom Count: 24
• Complexity: 600

Purity/Quality:

≥96% ^*data from raw suppliers

Tubotaiwine 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1C2CCN3C1C4(CC3)C5=CC=CC=C5NC4=C2C(=O)OC
• Isomeric SMILES: CC[C@H]1[C@@H]2CCN3[C@H]1[C@]4(CC3)C5=CC=CC=C5NC4=C2C(=O)OC

Technology Process of Tubotaiwine

There total 23 articles about Tubotaiwine 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: 91.0%

(+)-condylocarpine (4939-81-5,58074-72-9) → tubotaiwine (6711-69-9)

Guidance literature:

With platinum(IV) oxide; hydrogen; In ethanol; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1021/ol102709s

Reference yield: 20.0%

(3aRS,4SR,5SR,11bSR)-Methyl 4-ethyl-2,3,3a,4,5,7-hexahydro-3,5-ethano-1H-pyrrolo<2,3-d>carbazole-7-carboxylate (134734-63-7) → (+/-)-Tubotaiwine (6711-69-9,23365-76-6)

Guidance literature:

In methanol; for 0.5h; Irradiation;

DOI:10.1039/c39910000614 DOI:10.1021/jo00093a028

Reference yield:

(1RS,5RS,12SR)-2-Benzyl-12-ethyl-1,2,3,4,5,6-hexahydro-1,5-methanoazocino<4,3-b>indole (128350-30-1,128441-43-0) → (+/-)-Tubotaiwine (6711-69-9,23365-76-6)

Guidance literature:

Multi-step reaction with 7 steps

1: H₂ / Pd(OH)2 / methanol / 120 h

2: 72 percent / Na₂CO₃ / dioxane / 18 h / Heating

3: 79 percent / BF₃*Et₂O / CH₂Cl₂ / 4 h / 0 °C

4: dimethyl(methylthio)sulfonium fluoroborate / acetonitrile / 3 h / 0 °C

5: 50 percent / NaH / 1,2-dimethoxy-ethane / 1.) r.t., 15 min, 2.) 60 deg C, 1 h

6: 64 percent / Raney Ni W-2 / ethanol / 4 h / Heating

7: 20 percent / methanol / 0.5 h / Irradiation

With Raney Ni W-2; boron trifluoride diethyl etherate; dimethyl(methylthio)sulfonium tetrafluoroborate; hydrogen; sodium hydride; sodium carbonate; palladium dihydroxide; In 1,4-dioxane; methanol; 1,2-dimethoxyethane; ethanol; dichloromethane; acetonitrile;

DOI:10.1021/jo00093a028

upstream raw materials:

(+)-condylocarpine

(3aRS,4SR,5SR,11bSR)-Methyl 4-ethyl-2,3,3a,4,5,7-hexahydro-3,5-ethano-1H-pyrrolo<2,3-d>carbazole-7-carboxylate

C₁₆H₂₀N₂

(1RS,5RS,12SR)-2-Benzyl-12-ethyl-1,2,3,4,5,6-hexahydro-1,5-methanoazocino<4,3-b>indole

Refernces

• 1、 Gracia, Jordi,Casamitjana, Nuria,Bonjoch, Josep,Bosch, Joan. "Total Synthesis of Uleine-Type and Strychnos Alkaloids through a Common Intermediate". . p. 3939 - 3951. Retrieved 2007/10/02.
• 2、 Kuehne, Martin E.,Frasier, Deborah A.,Spitzer, Timothy D.. "Total Syntheses of Tubotaiwine and 19,20-Dihydro-20-epi-akuammicine". . p. 2696 - 2700. Retrieved 2007/10/02.