enanthotoxin

Base Information

• Chemical Name: enanthotoxin
• CAS No.: 20311-78-8
• Molecular Formula: C₁₇H₂₂O₂
• Molecular Weight: 258.36
• Mol file: 20311-78-8.mol

Synonyms:(+)-Heptadeca-2t,8t,10t-trien-4,6-diin-1,14-diol;Oenanthotoxin;(+)-heptadeca-2t,8t,10t-triene-4,6-diyne-1,14-diol;Enanthotoxin;(+)-Heptadeca-2t,8t,10t-trien-4,6-diin-1,14-diol,Oenanthotoxin;

Chemical Property of enanthotoxin

Chemical Property:

• Vapor Pressure: 2.42E-10mmHg at 25°C
• Melting Point: 87° (natural), 68° (synthetic)
• Refractive Index: 1.4770 (estimate)
• Boiling Point: 458.7°C at 760 mmHg
• Flash Point: 213.8°C
• PSA: 40.46000
• Density: 1.025g/cm³
• LogP: 2.59530

Purity/Quality:

99% ^*data from raw suppliers

ENANTHOTOXIN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of enanthotoxin

There total 23 articles about enanthotoxin 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: 82.6%

(7E,9E,15E)-17-hydroxy-7,9,15-heptadecatrien-11,13-diyn-4-one (20311-75-5) → (2E,8E,10E)-2,8,10-heptadecatrien-4,6-diyne-1,14-diol (463-02-5,20311-78-8,111128-27-9)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; at 25 ℃; for 2h;

DOI:10.1016/j.bmc.2015.07.031

Reference yield:

3,4-dihydro-2H-pyran (110-87-2) → (2E,8E,10E)-2,8,10-heptadecatrien-4,6-diyne-1,14-diol (463-02-5,20311-78-8,111128-27-9)

Guidance literature:

Multi-step reaction with 8 steps

1.1: N-Bromosuccinimide / methanol / 1 h / -10 - 25 °C

1.2: 10 h / Reflux

2.1: phosphoric acid / 60 °C

3.1: lithium chloride / tetrahydrofuran / -20 - 25 °C

4.1: phosphorus tribromide; pyridine / diethyl ether / 0.5 h / 0 °C / Reflux

5.1: N-ethyl-N,N-diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 0.17 h / -15 °C

5.2: 1 h / 20 °C

6.1: tetrahydrofuran; diethyl ether / 1 h / -15 °C

7.1: N-Bromosuccinimide; N-ethyl-N,N-diisopropylamine; copper(l) iodide / acetonitrile / 12 h / 25 °C

8.1: lithium aluminium tetrahydride / diethyl ether / 2 h / 25 °C

With pyridine; N-Bromosuccinimide; copper(l) iodide; lithium aluminium tetrahydride; n-butyllithium; phosphoric acid; phosphorus tribromide; N-ethyl-N,N-diisopropylamine; lithium chloride; In tetrahydrofuran; methanol; diethyl ether; hexane; acetonitrile; 5.1: |Weinreb Ketone Synthesis / 5.2: |Weinreb Ketone Synthesis / 7.1: |Glaser Coupling;

DOI:10.1016/j.bmc.2015.07.031

Reference yield:

trans-3-bromo-2-methoxytetrahydro-2H-pyran → (2E,8E,10E)-2,8,10-heptadecatrien-4,6-diyne-1,14-diol (463-02-5,20311-78-8,111128-27-9)

Guidance literature:

Multi-step reaction with 8 steps

1.1: potassium hydroxide / methanol / 6 h / Reflux

2.1: phosphoric acid / 60 °C

3.1: lithium chloride / tetrahydrofuran / -20 - 25 °C

4.1: phosphorus tribromide; pyridine / diethyl ether / 0.5 h / 0 °C / Reflux

5.1: N-ethyl-N,N-diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 0.17 h / -15 °C

5.2: 1 h / 20 °C

6.1: tetrahydrofuran; diethyl ether / 1 h / -15 °C

7.1: N-Bromosuccinimide; N-ethyl-N,N-diisopropylamine; copper(l) iodide / acetonitrile / 12 h / 25 °C

8.1: lithium aluminium tetrahydride / diethyl ether / 2 h / 25 °C

With pyridine; N-Bromosuccinimide; copper(l) iodide; lithium aluminium tetrahydride; n-butyllithium; phosphoric acid; phosphorus tribromide; N-ethyl-N,N-diisopropylamine; lithium chloride; potassium hydroxide; In tetrahydrofuran; methanol; diethyl ether; hexane; acetonitrile; 5.1: |Weinreb Ketone Synthesis / 5.2: |Weinreb Ketone Synthesis / 7.1: |Glaser Coupling;

DOI:10.1016/j.bmc.2015.07.031

upstream raw materials:

(7E,9E,15E)-17-hydroxy-7,9,15-heptadecatrien-11,13-diyn-4-one

17-acetoxy-heptadeca-7t,9t,15t-triene-11,13-diyn-4-ol

(E)-2-penten-4-yn-1-ol

6-methoxy-3,6-dihydro-2H-pyran

Downstream raw materials:

4-heptadecanol

heptadecan-4-one

oenanthotoxin-1-O-14-O-(S)-MTPA diester

oenanthotoxin-1-O-14-O-(R)-MTPA diester

Refernces