Ginsenoyne E

Base Information

• Chemical Name: Ginsenoyne E
• CAS No.: 126146-63-2
• Molecular Formula: C₁₇H₂₂O₂
• Molecular Weight: 258.36
• Nikkaji Number: J367.017A
• Wikidata: Q105306408
• Metabolomics Workbench ID: 47861
• Mol file: 126146-63-2.mol

Synonyms:Ginsenoyne E;8-(3-heptyloxiran-2-yl)oct-1-en-4,6-diyn-3-one;PQ 3;9,10-Epoxy-1-heptadecene-4,6-diyn-3-one;126146-63-2;3-Oxopanaxydol;Panaquinquecol 3;SCHEMBL10493749;CHEBI:173842;WIONCQLWGYLTME-UHFFFAOYSA-N;8-(3-Heptyloxiranyl)-1-octene-4,6-diyn-3-one, 9CI;1-Octene-4,6-diyn-3-one, 8-[(2R,3S)-3-heptyloxiranyl]-;8-((2R,3S)-3-Heptyloxiran-2-yl)octa-1-en-4,6-diyn-3-one;1-Octene-4,6-diyn-3-one, 8-(3-heptyloxiranyl)-, (2R-cis)-;1-Octene-4,6-diyn-3-one, 8-[(2R,3S)-3-heptyl-2-oxiranyl]-

Chemical Property of Ginsenoyne E

Chemical Property:

• Boiling Point: 369.2±34.0 °C(Predicted)
• PSA: 29.60000
• Density: 0.994±0.06 g/cm3(Predicted)
• LogP: 3.26630
• XLogP3: 5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 9
• Exact Mass: 258.161979940
• Heavy Atom Count: 19
• Complexity: 435

Purity/Quality:

98%Min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCC1C(O1)CC#CC#CC(=O)C=C

Technology Process of Ginsenoyne E

There total 7 articles about Ginsenoyne 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: 67.0%

(3RS,9R,10S)-panaxydol (500763-15-5) → (9R,10S)-3-oxo-panaxydol (126146-63-2)

Guidance literature:

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; Oxone; tetrabutylammomium bromide; In toluene; for 3.5h;

DOI:10.3987/com-02-s25

Reference yield:

(3S,9R,10S)-9,10-epoxyheptadec-1-ene-4,6-diyn-3-ol (664980-96-5) → (9R,10S)-3-oxo-panaxydol (126146-63-2)

Guidance literature:

With manganese(IV) oxide; In acetone; at 40 ℃; for 3h;

DOI:10.1055/s-2006-957763

Reference yield:

rac-hept-1-ene-4,6-diyn-3-ol (14304-31-5) → (9R,10S)-3-oxo-panaxydol (126146-63-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-BuLi; DMPU / tetrahydrofuran / 1 h / -78 °C

1.2: 47 percent / 16 h / -78 °C

2.1: 67 percent / TEMPO; nBu₄Br; oxone / toluene / 3.5 h

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 2,2,6,6-tetramethyl-piperidine-N-oxyl; Oxone; n-butyllithium; tetrabutylammomium bromide; In tetrahydrofuran; toluene;

DOI:10.3987/com-02-s25

upstream raw materials:

(3RS,9R,10S)-panaxydol

(3S,9R,10S)-9,10-epoxyheptadec-1-ene-4,6-diyn-3-ol

(6R,7S)-6,7-epoxytetradeca-1,3-diyne

rac-hept-1-ene-4,6-diyn-3-ol

Refernces

• 1、 Hirakura, Kazuhiro,Morita, Makoto,Nakajima, Kaoru,Ikeya, Yukinobu,Mitsuhashi, Hiroshi. "POLYACETYLENES FROM THE ROOTS OF PANAX GINSENG". . p. 3327 - 3333. Retrieved 1991.
• 2、 Baldwin, Jack E.,Adlington, Robert M.,Wilkinson, Peter J.,Marquez, Rodolfo,Adamo, Mauro F. A.. "Studies towards the biomimetic synthesis of ginsenoyne L; efficient synthesis of 2′-epi-ginsenoyne L". . p. 81 - 85. Retrieved 2007/10/03.