Teuclatriol

Base Information

• Chemical Name: Teuclatriol
• CAS No.: 152110-17-3
• Molecular Formula: C₁₅H₂₈O₃
• Molecular Weight: 256.386
• Mol file: 152110-17-3.mol

Synonyms:1,4,8-Azulenetriol,decahydro-1,4-dimethyl-7-(1-methylethyl)-, [1S-(1a,3ab,4b,7a,8a,8aa)]-; Teuclatriol

Chemical Property of Teuclatriol

Chemical Property:

• Boiling Point: 382.1±37.0 °C(Predicted)
• PKA: 14.62±0.70(Predicted)
• PSA: 60.69000
• Density: 1.075±0.06 g/cm3(Predicted)
• LogP: 1.94150

Purity/Quality:

98%min ^*data from raw suppliers

Teuclatriol ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Teuclatriol

There total 20 articles about Teuclatriol 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: 52.0%

(-)-4β,6β-dihydroxy-1α,5β(H)-guai-9-ene → (-)-teuclatriol (151563-36-9,152110-17-3) + (-)-10-epiteuclatriol (151563-36-9,152110-17-3)

Guidance literature:

(-)-4β,6β-dihydroxy-1α,5β(H)-guai-9-ene; With oxygen; cobalt acetylacetonate; In tetrahydrofuran; at 20 ℃; for 1h;

With phenylsilane; oxygen; In tetrahydrofuran; at 20 ℃; for 14h;

DOI:10.1021/ol5032975

Reference yield: 52.0%

(-)-4β,6β-dihydroxy-1α,5β(H)-guai-9-ene → (-)-teuclatriol (151563-36-9,152110-17-3) + (-)-10-epiteuclatriol (151563-36-9,152110-17-3)

Guidance literature:

(-)-4β,6β-dihydroxy-1α,5β(H)-guai-9-ene; With oxygen; cobalt acetylacetonate; In tetrahydrofuran; at 20 ℃; for 1h;

With phenylsilane; oxygen; In tetrahydrofuran; at 20 ℃; for 14h;

DOI:10.1021/ol5032975

Reference yield:

(2-furyl)methyl alcohol (98-00-0,25212-86-6,93793-62-5) → (-)-teuclatriol (151563-36-9,152110-17-3) + (-)-10-epiteuclatriol (151563-36-9,152110-17-3)

Guidance literature:

Multi-step reaction with 9 steps

1.1: water / pH 4 / Large scale

2.1: Inert atmosphere

3.1: caesium carbonate; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; (1R,2R)-1,2-bis[(2-diphenylphosphanyl)benzoylamino]cyclohexane / dichloromethane / Inert atmosphere; Resolution of racemate

4.1: copper(l) cyanide; lithium chloride / tetrahydrofuran / 0.07 h / -78 °C / Inert atmosphere

4.2: 0.08 h / -78 °C / Inert atmosphere; Resolution of racemate

5.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 44 °C / Inert atmosphere

6.1: diphenylsilane; zinc(II) chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / chloroform / 0.33 h / 20 °C

7.1: 1H-imidazole / N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere

8.1: cerium(III) chloride heptahydrate / tetrahydrofuran; diethyl ether / 0.5 h / -78 °C / Inert atmosphere

8.2: 4 h / -78 °C / Inert atmosphere

8.3: 0.58 h / 0 - 20 °C / Inert atmosphere

9.1: cobalt acetylacetonate; oxygen / tetrahydrofuran / 1 h / 20 °C

9.2: 14 h / 20 °C

With 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; tetrakis(triphenylphosphine) palladium⁽⁰⁾; cerium(III) chloride heptahydrate; diphenylsilane; oxygen; copper(l) cyanide; caesium carbonate; (1R,2R)-1,2-bis[(2-diphenylphosphanyl)benzoylamino]cyclohexane; cobalt acetylacetonate; lithium chloride; zinc(II) chloride; In tetrahydrofuran; diethyl ether; dichloromethane; chloroform; water; N,N-dimethyl-formamide;

DOI:10.1021/ol5032975

upstream raw materials:

4β,10β-dihydroxy-6β-acetoxy-cis-1β-H,5β-H-guaiane

4β-hydroxy-6β,10β-diacetoxy-cis-1β-H,5β-H-guaiane

(2-furyl)methyl alcohol

4-Hydroxycyclopent-2-enone