jolkinolide E

Base Information

• Chemical Name: jolkinolide E
• CAS No.: 54494-34-7
• Molecular Formula: C20H28O2
• Molecular Weight: 300.44
• Mol file: 54494-34-7.mol

Synonyms:jolkinolide E;helioscopoindolide G;(4aR,10aR,11aR,11bR)-4,4,8,11b-Tetramethyl-2,3,4,4a,5,6,10a,11,11a,11b-decahydro-1H-10-oxa-cyclopenta[b]phenanthren-9-one;

Chemical Property of jolkinolide E

Chemical Property:

• Melting Point: 182.3 °C
• Boiling Point: 458.5±24.0 °C(Predicted)
• PSA: 26.30000
• Density: 1.09±0.1 g/cm3(Predicted)
• LogP: 4.80100

Purity/Quality:

Analysis control,HPLC≥95% ^*data from raw suppliers

JolkinolideE 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of jolkinolide E

There total 21 articles about jolkinolide E 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%

2-(Diethoxy-phosphoryl)-propionic acid (3R,4aR,4bR,8aR)-4b,8,8-trimethyl-2-oxo-2,3,4,4a,4b,5,6,7,8,8a,9,10-dodecahydro-phenanthren-3-yl ester (84162-38-9) → jolkinolide E (54494-34-7)

Guidance literature:

With sodium hydride; In 1,2-dimethoxyethane; for 0.5h; Ambient temperature;

DOI:10.1246/cl.1982.1689

Reference yield: 69.5%

12-(2-diethylphosphonopropionyloxy)-Δ8(14)-podocarpen-13-one (84162-38-9) → jolkinolide E (54494-34-7,84236-10-2,100761-23-7)

Guidance literature:

With sodium hydride; In 1,2-dimethoxyethane; for 0.5h; Ambient temperature;

DOI:10.1016/0040-4020(89)80132-2

Reference yield:

4,4,10-trimethyl-9-methylidene-Δ6-8-octalone (84162-35-6,91547-82-9) → jolkinolide E (54494-34-7,84236-10-2,100761-23-7)

Guidance literature:

Multi-step reaction with 9 steps

1: Na / methanol / 40 h / Ambient temperature

2: 1percent aq. NaOH / methanol; H₂O / 15 h / 15 °C

3: benzene / 1 h / Heating

4: H₂ / 10percent Pd-C / 1,2-dimethoxy-ethane / 1.5 h / 28 °C

5: 1percent aq. NaOH / methanol; H₂O / 0.5 h / Heating

6: 1.) diisopropylamine, n-BuLi / 1.) hexane, DME, -15 deg C, 10 min; 2.) hexane, DME, -15 deg C to rt 1.5 h

7: 1.) MCPBA; 2.) Bu₄NF*3H₂O / 1.) hexane, rt, 40 min; 2.) CH₂Cl₂, rt, overnight

8: 92 percent / dimethylaminopyridine / benzene / 0.17 h / Ambient temperature

9: 69.5 percent / NaH (60percent in oil) / 1,2-dimethoxy-ethane / 0.5 h / Ambient temperature

With dmap; sodium hydroxide; n-butyllithium; tetrabutyl ammonium fluoride; hydrogen; sodium; sodium hydride; diisopropylamine; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In methanol; 1,2-dimethoxyethane; water; benzene;

DOI:10.1016/0040-4020(89)80132-2

upstream raw materials:

12-(2-diethylphosphonopropionyloxy)-Δ⁸⁽¹⁴⁾-podocarpen-13-one

Δ⁸⁽¹⁴⁾-podocarpen-13-one

4,4,10-trimethyl-9-methylidene-Δ⁶-8-octalone

1-(hydroxymethyl)-5,5,8a-trimethyl-4a,5,6,7,8,8a-hexahydronaphthalen-2(1H)-one

Refernces

• 1、 Katsumura, Shigeo,Isoe, Sachiniko. "AN EFFICIENT SYNTHESIS OF JOLKINOLIDE E INVOLVING THE BUTENOLIDE RING FORMATION". . p. 1689 - 1692. Retrieved 2007/10/02.