(-)-dihydroedulan II

Base Information

• Chemical Name: (-)-dihydroedulan II
• CAS No.: 41678-32-4
• Molecular Formula: C13H22O
• Molecular Weight: 194.317
• DSSTox Substance ID: DTXSID601316713
• Nikkaji Number: J238.383G
• Wikidata: Q27159863
• Mol file: 41678-32-4.mol

Synonyms:(-)-dihydroedulan II;Dihydroedulan II;SCHEMBL20873434;CHEBI:87716;DTXSID601316713;Q27159863;(2S,4aR,8aS)-2,5,5,8a-tetramethyl-3,4,4a,6-tetrahydro-2H-chromene;3,4,4abeta,5,6,8a-Hexahydro-2beta,5,5,8abeta-tetramethyl-2H-1-benzopyran;(2S,4aR,8aS)-2,5,5,8a-tetramethyl-3,4,4a,5,6,8a-hexahydro-2H-1-benzopyran

Chemical Property of (-)-dihydroedulan II

Chemical Property:

• Boiling Point: 239.3°Cat760mmHg
• Flash Point: 94.4°C
• Density: 0.899g/cm³
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 194.167065321
• Heavy Atom Count: 14
• Complexity: 254

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1CCC2C(CC=CC2(O1)C)(C)C
• Isomeric SMILES: C[C@H]1CC[C@H]2[C@@](O1)(C=CCC2(C)C)C

Technology Process of (-)-dihydroedulan II

There total 40 articles about (-)-dihydroedulan II 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%

dihydro-α-ionol (13720-37-1) → 2,6,10,10-tetramethyl-1-oxaspiro[4.5]dec-6-ene (36431-72-8,59872-09-2,79516-57-7,169102-88-9,43126-21-2,43126-22-3,66537-39-1,66537-40-4) + dl-dihydroedulan (41678-32-4,63335-66-0,72746-44-2,74006-61-4,74006-62-5,122797-82-4)

Guidance literature:

With bis(p-chlorophenyl) diselenide; tetraethylammonium perchlorate; In water; acetonitrile; at 65 - 70 ℃; electrochemical oxidation;

DOI:10.1016/S0040-4039(00)98772-0

Reference yield: 46.0%

C20H30N2O3S → (-)-dihydroedulan II (41678-32-4)

Guidance literature:

With sodium hydride; In toluene; for 1.5h; Heating;

Reference yield:

alpha-ionone (127-41-3,6901-97-9,14398-36-8,24190-29-2,30685-95-1,31798-12-6,52340-45-1,67529-94-6,67529-95-7) → (-)-dihydroedulan II (41678-32-4)

Guidance literature:

Multi-step reaction with 9 steps

1: 1) H₂, KOH, 2) NaBH₄ / 1) 10percent Pd/C / 1) EtOH, 3 h, rt, 2) 12 h, rt

2: 50 percent / vinyl acetate / 24 h / 22 °C / lipase PS

3: 96 percent / phosphate buffer (pH 7) / 20 h / 30 °C / lipase PS

4: 94 percent / pyridine / CH₂Cl₂ / 48 h / 0 °C

5: 64 percent / monoperoxyphthalic acid monomagnesium salt / propan-2-ol; H₂O / 12 h / Ambient temperature

6: 60 percent / 37percent aq. HClO₄ / tetrahydrofuran; H₂O / 48 h / Ambient temperature

7: 35 percent / 60percent NaH / tetrahydrofuran / 2 h / 70 °C

8: 96 percent / CrO₃, 6 N H₂SO₄ / acetone / 0.5 h / Ambient temperature

9: 2) NaH / 1) aq. MeOH, 2) toluene

With pyridine; chromium(VI) oxide; potassium hydroxide; sodium tetrahydroborate; vinyl acetate; perchloric acid; phosphate buffer; sulfuric acid; hydrogen; sodium hydride; magnesium monoperoxyphthalate hexahydrate; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; isopropyl alcohol; acetone;

DOI:10.1016/S0040-4020(01)89725-8

upstream raw materials:

dihydro-α-ionol

(2R,4aR,8R,8aR)-8-(4-Chloro-phenylselanyl)-2,5,5,8a-tetramethyl-octahydro-chromene

9-hydroxymegastigma-4,7-dien-3-one

(1R,3S,6R)-(-)-1,3,7,7-tetramethyl-2-oxabicyclo<4.4.0>decan-10-one

Refernces

• 1、 Mori, Kenji,Aki, Shinji,Kido, Masaru. "Pheromone Synthesis, CXLVII. Synthesis of (1R,3S,6R,9S,10S)-9,10-Epoxytetrahydroedulan, the Main Component of the Hairpencil Secretion of Male Danaid Butterfly Eupoloea klugii". . p. 83 - 90. Retrieved 2007/10/02.
• 2、 Francke, Wittko,Schulz, Stefan,Sinnwell, Volker,Koenig, Wilfried A.,Roisin, Yves. "Epoxytetrahydroedulan, a New Terpenoid from the Hairpencils of Euploea (Lep.: Danainae) Butterflies". . p. 1195 - 1202. Retrieved 2007/10/02.