(+-)-Epiboxidine

Base Information

• Chemical Name: (+-)-Epiboxidine
• CAS No.: 188895-96-7
• Molecular Formula: C₁₀H₁₄N₂O
• Molecular Weight: 178.234
• UNII: XI646L2ARJ
• DSSTox Substance ID: DTXSID20172258
• Nikkaji Number: J816.882B
• Wikipedia: Epiboxidine
• Wikidata: Q5382428
• Mol file: 188895-96-7.mol

Synonyms:epiboxidine;exo-2-(3-methyl-5-isoxazolyl)-7-azbicyclo(2.2.1)heptane

Chemical Property of (+-)-Epiboxidine

Chemical Property:

• Vapor Pressure: 0.000507mmHg at 25°C
• Melting Point: 200-205 °C (decomp)
• Boiling Point: 313.1°Cat760mmHg
• PKA: 10.14±0.40(Predicted)
• Flash Point: 143.2°C
• PSA: 38.06000
• Density: 1.13g/cm³
• LogP: 2.72170
• Storage Temp.: −20°C
• Solubility.: H2O: 22 mg/mL
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 178.110613074
• Heavy Atom Count: 13
• Complexity: 209

Purity/Quality:

99% ^*data from raw suppliers

Epiboxidine hydrochloride ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=NOC(=C1)C2CC3CCC2N3
• Isomeric SMILES: CC1=NOC(=C1)[C@H]2C[C@@H]3CC[C@H]2N3

Technology Process of (+-)-Epiboxidine

There total 18 articles about (+-)-Epiboxidine 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: 62.5%

exo-7-(tert-butoxycarbonyl)-7-azabicyclo[2.2.1]heptan-1,3-butanedione-3-oxime → (+/-)-epiboxidine (188895-96-7)

Guidance literature:

With hydrogenchloride; at 90 - 95 ℃; for 3h;

DOI:10.1248/cpb.47.1501

Reference yield: 55.0%

(+/-)-2exo-(3-methyl-isoxazol-5-yl)-7-(toluene-4-sulfonyl)-7-azabicyclo[2.2.1]heptane → (+/-)-epiboxidine (188895-96-7)

Guidance literature:

With hydrogen bromide; phenol; for 3h; Heating;

DOI:10.1021/jo701536a

Reference yield:

7-benzyl-2-carbethoxy-7-azabicyclo<2.2.1>heptane → (+/-)-epiboxidine (188895-96-7)

Guidance literature:

Multi-step reaction with 5 steps

1: H₂ / Pd(OH)2 / ethanol / 48 h / 2585.74 Torr

2: Et₃N / CH₂Cl₂ / 18 h / Ambient temperature

3: K₂CO₃ / methanol / 1 h / Heating

4: SOCl₂ / 10 h / 0 °C

5: 1.) n-BuLi, 3.) conc. HCl / 1.) THF, hexane, 0 deg C to room temperature, 30 min, 2.) THF, refluxm 45 min, 3.) 80 deg C, 4 h

With hydrogenchloride; n-butyllithium; thionyl chloride; hydrogen; potassium carbonate; triethylamine; palladium dihydroxide; In methanol; ethanol; dichloromethane;

DOI:10.1021/jo9903757

upstream raw materials:

7-(tert-butyloxycarbonyl)-2-exo-carbethoxy-7-azabicyclo<2.2.1>heptane

acetone oxime

N-carbethoxytropinone

tropinone