Rhombifoline

Base Information

• Chemical Name: Rhombifoline
• CAS No.: 529-78-2
• Molecular Formula: C₁₅H₂₀N₂O
• Molecular Weight: 244.337
• DSSTox Substance ID: DTXSID501118132
• Nikkaji Number: J102.936C
• Wikidata: Q105384597
• Metabolomics Workbench ID: 123435
• ChEMBL ID: CHEMBL1397610
• Mol file: 529-78-2.mol

Synonyms:rhombifoline

Chemical Property of Rhombifoline

Chemical Property:

• Vapor Pressure: 6.64E-08mmHg at 25°C
• Boiling Point: 438.9°Cat760mmHg
• PKA: 9.45±0.20(Predicted)
• Flash Point: 202.3°C
• PSA: 25.24000
• Density: 1.14g/cm³
• LogP: 1.78140
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 244.157563266
• Heavy Atom Count: 18
• Complexity: 424

Purity/Quality:

98%min ^*data from raw suppliers

Rhombifoline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=CCCN1CC2CC(C1)C3=CC=CC(=O)N3C2
• Isomeric SMILES: C=CCCN1C[C@@H]2C[C@H](C1)C3=CC=CC(=O)N3C2
• Description: A minor alkaloid obtained from Thermopsis rhombifolia (Watt), Richards, the base was originally given the empirical formula ClsH2002N2, but subsequently changed to that given. It is strongly laevorotatory with [α]25D - 232.4° (c 2.13, EtOH) and yields crystalline salts including the hydrochloride, m.p. 256-8°C (dec.) which sublimes at l20°CjO.000l mm; the perchlorate, m.p. 243-5°C (dec.); platinichloride, m.p. 268° C and the picrate, m.p. 226°C (dec.).

Technology Process of Rhombifoline

There total 5 articles about Rhombifoline 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: 51.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + allyl bromide (106-95-6) + cytisine (485-35-8) → (-)-rhombifoline (529-78-2)

Guidance literature:

With copper(l) iodide; acetic acid; zinc; In water; at 20 ℃; for 22h;

DOI:10.1002/anie.201712852

Reference yield:

(1R,5R)-6-methyl-3,7-diazabicyclo[3.3.1]non-6-en-2-one → (-)-rhombifoline (529-78-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: triethylamine; dmap / dichloromethane / 20 h

2.1: triethylamine / tetrahydrofuran / 5 h / 20 °C

3.1: methanol; sodium tetrahydroborate / 2 h / 0 - 20 °C

3.2: 15 h / -78 - 20 °C

4.1: acetic acid; zinc; copper(l) iodide / water / 22 h / 20 °C

With methanol; dmap; sodium tetrahydroborate; copper(l) iodide; acetic acid; triethylamine; zinc; In tetrahydrofuran; dichloromethane; water;

DOI:10.1002/anie.201712852

Reference yield:

(1R,5R)-3-tert-butoxycarbonyl-6-methyl-3,7-diazabicyclo[3.3.1]non-6-en-2-one → (-)-rhombifoline (529-78-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: triethylamine / tetrahydrofuran / 5 h / 20 °C

2.1: methanol; sodium tetrahydroborate / 2 h / 0 - 20 °C

2.2: 15 h / -78 - 20 °C

3.1: acetic acid; zinc; copper(l) iodide / water / 22 h / 20 °C

With methanol; sodium tetrahydroborate; copper(l) iodide; acetic acid; triethylamine; zinc; In tetrahydrofuran; water;

DOI:10.1002/anie.201712852

upstream raw materials:

3-butenyl chloride

cytisine

formaldehyd

allyl bromide

Downstream raw materials:

(-)-tsukushinamine-B

(-)-tsukushinamine-A

Refernces

• 1、 Scharnagel, Dagmar,Goller, Jessica,Deibl, Nicklas,Milius, Wolfgang,Breuning, Matthias. "The Enantioselective Total Synthesis of Bisquinolizidine Alkaloids: A Modular “Inside-Out” Approach". . p. 2432 - 2435. Retrieved 2018/02/16.