Paspalicine

Base Information

• Chemical Name: Paspalicine
• CAS No.: 11024-55-8
• Molecular Formula: C₂₇H₃₁NO₃
• Molecular Weight: 417.548
• UNII: J35628M7AA
• Metabolomics Workbench ID: 164841
• Nikkaji Number: J1.386.480B
• Wikidata: Q27281117
• Mol file: 11024-55-8.mol

Synonyms:paspalicine

Chemical Property of Paspalicine

Chemical Property:

• Vapor Pressure: 1.15E-13mmHg at 25°C
• Melting Point: 230 °C (decomp)(Solv: methanol (67-56-1))
• Boiling Point: 584.9°Cat760mmHg
• PKA: 17.72±0.70(Predicted)
• Flash Point: 307.6°C
• PSA: 51.32000
• Density: 1.28g/cm³
• LogP: 5.20740
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 417.23039385
• Heavy Atom Count: 31
• Complexity: 880

Purity/Quality:

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C2C(=O)C=C3C4CCC5CC6=C(C5(C4(CCC3(O2)O1)C)C)NC7=CC=CC=C67)C
• Isomeric SMILES: C[C@]12CC[C@]34C(=CC(=O)[C@H](O3)C(O4)(C)C)[C@@H]1CC[C@@H]5[C@@]2(C6=C(C5)C7=CC=CC=C7N6)C

Technology Process of Paspalicine

There total 19 articles about Paspalicine 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: 70.0%

C27H31NO3 (129896-05-5) → Paspalicine (11024-55-8,138331-69-8)

Guidance literature:

With rhodium(III) chloride; In ethanol; benzene; for 17h; Heating;

DOI:10.1021/ja00178a071

Reference yield:

[(2S)-3,3-dimethyloxiran-2-yl]methanol (116347-29-6) → Paspalicine (11024-55-8,138331-69-8)

Guidance literature:

Multi-step reaction with 11 steps

1: 65 percent / Et₃N / CH₂Cl₂

2: 80 percent / H₂SO₄ / benzene

3: 97 percent / K₂CO₃ / ethanol

4: 80 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂

5: 72 percent / DMSO, NaH / tetrahydrofuran

7: 84 percent / Py, DMAP

8: 1.) MeI, 2.) HCO₂Na / 1.) MeCN, RT, 2.) MeO(CH₂)2OH, 110 deg C, 20 h

9: 76 percent / 70percent HClO₄ / CH₂Cl₂ / 1 h / 0 °C

10: 95 percent / K₂CO₃ / methanol

11: DCC, TFA, Py, DMSO / benzene

With pyridine; dmap; perchloric acid; oxalyl dichloride; sulfuric acid; sodium formate; sodium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; methyl iodide; In tetrahydrofuran; methanol; ethanol; dichloromethane; benzene;

DOI:10.1021/ja00178a071

Reference yield:

(S)-(3,3-dimethyl-1,4-dioxaspiro[4.4]nonan-2-yl)methanol (129896-06-6) → Paspalicine (11024-55-8,138331-69-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 80 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂

2: 72 percent / DMSO, NaH / tetrahydrofuran

4: 84 percent / Py, DMAP

5: 1.) MeI, 2.) HCO₂Na / 1.) MeCN, RT, 2.) MeO(CH₂)2OH, 110 deg C, 20 h

6: 76 percent / 70percent HClO₄ / CH₂Cl₂ / 1 h / 0 °C

7: 95 percent / K₂CO₃ / methanol

8: DCC, TFA, Py, DMSO / benzene

With pyridine; dmap; perchloric acid; oxalyl dichloride; sodium formate; sodium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; methyl iodide; In tetrahydrofuran; methanol; dichloromethane; benzene;

DOI:10.1021/ja00178a071

upstream raw materials:

C₂₇H₃₃NO₃

C₂₇H₃₁NO₃

[(2S)-3,3-dimethyloxiran-2-yl]methanol

(S)-(3,3-dimethyl-1,4-dioxaspiro[4.4]nonan-2-yl)methanol

Downstream raw materials:

Paspalinine

C₂₇H₃₁NO₅

Refernces

• 1、 Smith III,Sunazuka,Leenay,Kingery-Wood. "Total synthesis of (+)-paspalicine and (+)-paspalinine". . p. 8197 - 8198. Retrieved 2007/10/02.