Ehhpoh

Base Information

• Chemical Name: Ehhpoh
• CAS No.: 113704-34-0
• Molecular Formula: C₂₄H₃₀O₆
• Molecular Weight: 414.499
• Mol file: 113704-34-0.mol

Synonyms:7-(5,6-epoxy-3-(3-hydroxy-5-(4-hydroxyphenyl)-1-pentenyl)-7-oxabicyclo(2.2.1)hept-2-yl)-5-heptenoic acid;EHHPOH

Chemical Property of Ehhpoh

Chemical Property:

• Vapor Pressure: 1.3E-17mmHg at 25°C
• Boiling Point: 646.8°Cat760mmHg
• Flash Point: 222.4°C
• PSA: 99.52000
• Density: 1.293g/cm³
• LogP: 3.22390
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 11
• Exact Mass: 414.20423867
• Heavy Atom Count: 30
• Complexity: 638

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1CCC(C=CC2C(C3C4C(C2O3)O4)CC=CCCCC(=O)O)O)O
• Isomeric SMILES: C1=CC(=CC=C1CC[C@H](/C=C/[C@@H]2[C@@H]([C@H]3[C@@H]4[C@H]([C@@H]2O3)O4)C/C=C\CCCC(=O)O)O)O

Technology Process of Ehhpoh

There total 17 articles about Ehhpoh 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:

exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride (6118-51-0) → <1α,2β(5Z),3β(1E,3S),4α,5α,6α>-7-<5,6-epoxy-3-<3-hydroxy-5-(p-hydroxyphenyl)-1-pentenyl>-7-oxabicyclo<2.2.1>hept-2-yl>-5-heptenoic acid (113704-34-0)

Guidance literature:

Multi-step reaction with 17 steps

1: 92 percent / LiAlH₄ / tetrahydrofuran / 24 h / 25 °C

2: toluene / 0.25 h / 0 - 5 °C

3: pyridine / CH₂Cl₂ / 0.5 h / -50 °C

4: 100 percent / p-TsOH / 8 h / Heating

5: pyridine / 24 h / 25 °C

6: 75 percent / dimethylsulfoxide / 2 h / 90 - 95 °C

7: 75 percent / K₂CO₃ / methanol; H₂O / 6 h / 25 °C

8: 86 percent / p-TsOH / CH₂Cl₂ / 4 h / 0 - 5 °C

9: 93 percent / MCPBA / CH₂Cl₂ / 6 h / 25 °C

10: 73 percent / DIBAH / toluene / 4 h / -78 °C

11: 1.) potassium tert-amylate / 1.) THF, toluene, 0 deg C, 30 min; 25 deg C, 1 h, 2.) -20 deg C, 2 h; 0 deg C, 15 min

12: diethyl ether

13: 91 percent / amberlyst-15 acid exchange resin / methanol / 6 h / 25 °C

14: 83 percent / pyridinium chloroformate, Celite / CH₂Cl₂ / 4 h / 25 °C

15: 1.) LiBr, Et₃N / 1.) CH₂Cl₂, 25 deg C, 15 min, 2.) 25 deg C, overnight

16: 1.) CeCl₃, 2.) NaBH₄ / 1.) THF, MeOH, 25 deg C, 10 min, 2.) -50 deg C, 1 h

17: LiOH / tetrahydrofuran; H₂O / 8 h / 25 °C

With pyridine; lithium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; cerium(III) chloride; pyridinium chloroformate; amberlyst-15 acid exchange resin; Celite; diisobutylaluminium hydride; potassium 2-methylbutan-2-olate; potassium carbonate; toluene-4-sulfonic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium bromide; In tetrahydrofuran; pyridine; methanol; diethyl ether; dichloromethane; water; dimethyl sulfoxide; toluene;

DOI:10.1021/jm00400a007

Reference yield:

(Z)-7-((1S,2S,4R,5R,6R,7S)-7-{(E)-(S)-5-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-3-hydroxy-pent-1-enyl}-3,8-dioxa-tricyclo[3.2.1.02,4]oct-6-yl)-hept-5-enoic acid methyl ester → <1α,2β(5Z),3β(1E,3S),4α,5α,6α>-7-<5,6-epoxy-3-<3-hydroxy-5-(p-hydroxyphenyl)-1-pentenyl>-7-oxabicyclo<2.2.1>hept-2-yl>-5-heptenoic acid (113704-34-0)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water; at 25 ℃; for 8h; Yield given;

DOI:10.1021/jm00400a007

Reference yield:

exo-2,3-bis(hydroxymethyl)-7-oxabicyclo[2.2.1]hept-5-ene (106137-27-3,817201-06-2) → <1α,2β(5Z),3β(1E,3S),4α,5α,6α>-7-<5,6-epoxy-3-<3-hydroxy-5-(p-hydroxyphenyl)-1-pentenyl>-7-oxabicyclo<2.2.1>hept-2-yl>-5-heptenoic acid (113704-34-0)

Guidance literature:

Multi-step reaction with 16 steps

1: toluene / 0.25 h / 0 - 5 °C

2: pyridine / CH₂Cl₂ / 0.5 h / -50 °C

3: 100 percent / p-TsOH / 8 h / Heating

4: pyridine / 24 h / 25 °C

5: 75 percent / dimethylsulfoxide / 2 h / 90 - 95 °C

6: 75 percent / K₂CO₃ / methanol; H₂O / 6 h / 25 °C

7: 86 percent / p-TsOH / CH₂Cl₂ / 4 h / 0 - 5 °C

8: 93 percent / MCPBA / CH₂Cl₂ / 6 h / 25 °C

9: 73 percent / DIBAH / toluene / 4 h / -78 °C

10: 1.) potassium tert-amylate / 1.) THF, toluene, 0 deg C, 30 min; 25 deg C, 1 h, 2.) -20 deg C, 2 h; 0 deg C, 15 min

11: diethyl ether

12: 91 percent / amberlyst-15 acid exchange resin / methanol / 6 h / 25 °C

13: 83 percent / pyridinium chloroformate, Celite / CH₂Cl₂ / 4 h / 25 °C

14: 1.) LiBr, Et₃N / 1.) CH₂Cl₂, 25 deg C, 15 min, 2.) 25 deg C, overnight

15: 1.) CeCl₃, 2.) NaBH₄ / 1.) THF, MeOH, 25 deg C, 10 min, 2.) -50 deg C, 1 h

16: LiOH / tetrahydrofuran; H₂O / 8 h / 25 °C

With pyridine; lithium hydroxide; sodium tetrahydroborate; cerium(III) chloride; pyridinium chloroformate; amberlyst-15 acid exchange resin; Celite; diisobutylaluminium hydride; potassium 2-methylbutan-2-olate; potassium carbonate; toluene-4-sulfonic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium bromide; In tetrahydrofuran; pyridine; methanol; diethyl ether; dichloromethane; water; dimethyl sulfoxide; toluene;

DOI:10.1021/jm00400a007

upstream raw materials:

exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride

exo-2,3-bis(hydroxymethyl)-7-oxabicyclo[2.2.1]hept-5-ene

exo-cis-7-oxabicyclo<2.2.1>hept-5-ene-2,3-dimethanol carbonate

Refernces