2H-Pyran-2-one, tetrahydro-6-(2-pentenyl)-

Base Information

• Chemical Name: 2H-Pyran-2-one, tetrahydro-6-(2-pentenyl)-
• CAS No.: 25524-95-2
• Molecular Formula: C₁₀H₁₆O₂
• Molecular Weight: 168.236
• European Community (EC) Number: 247-074-2,252-148-2
• DSSTox Substance ID: DTXSID001347059
• Nikkaji Number: J596.589F,J250.948B
• Wikipedia: Jasmine_lactone
• Metabolomics Workbench ID: 46162
• Mol file: 25524-95-2.mol

Synonyms:6-[(E)-pent-2-enyl]oxan-2-one;2H-Pyran-2-one, tetrahydro-6-(2-pentenyl)-;34686-71-0;EINECS 252-148-2;Jasminlactone;2H-Pyran-2-one, tetrahydro-6-(2-penten-1-yl)-;creamy lactone;(-)-(Z)-Tetrahydro-6-(2-pentenyl)-2H-pyran-2-one;25524-95-2;(Z)-7-DECEN-5-OLIDE;cis-7-decen-5-olide;Tetrahydro-6-(2-pentenyl)-2H-pyran-2-one;Dec-7(Z)-en-5-olide;(Z)-Dec-7-en-5-olide;tetrahydro-6-(2z)-2-pentenyl-2h-pyran-2-one;Tetrahydro-6-(2Z)-2-penten-1-yl-2H-Pyran-2-one;SCHEMBL919912;SCHEMBL919914;cis-5-(2-Pentenyl)pentanolide;FEMA 3745;XPPALVZZCMPTIV-ONEGZZNKSA-N;DTXSID001347059;6-(pent-2-en-1-yl)oxan-2-one;AKOS006281379;100428-67-9;(Z)-dec-7-en-5-olide [jasmine lactone];6-(2-Pentenyl)tetrahydro-2H-pyran-2-one;6-[(2E)-pent-2-en-1-yl]oxan-2-one;(E)-6-(pent-2-enyl)tetrahydro-2H-pyran-2-one;tetrahydro-6-(2-pentenyl)-(z)-2h-pyran-2-one;Tetrahydro-6-[(E)-2-pentenyl]-2H-pyran-2-one;2H-Pyran-2-one,tetrahydro-6-(2-penten-1-yl)-;EN300-18533826;Tetrahydro-6-((Z)-2-penten-1-yl)-2H-Pyran-2-one;5-Hydroxy-7(Z)-decenoic acid-laquo deltaRaquo -lactone;tetrahydro - 6 - (2 - pentenyl) - 2H - pyran - 2 - one;25524-96-3

Chemical Property of 2H-Pyran-2-one, tetrahydro-6-(2-pentenyl)-

Chemical Property:

• Appearance/Colour: colourless to light yellow liquid with a coconut, fatty, fruity, peach, jasmine, woody, balsamic odour
• Vapor Pressure: 0.00355mmHg at 25°C
• Refractive Index: 1.462
• Boiling Point: 281.5 °C at 760 mmHg
• Flash Point: 113.1 °C
• PSA: 26.30000
• Density: 0.962 g/cm³
• LogP: 2.43840
• Water Solubility.: 5.05g/L at 20℃
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 168.115029749
• Heavy Atom Count: 12
• Complexity: 173

Purity/Quality:

99.9% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC=CCC1CCCC(=O)O1
• Isomeric SMILES: CC/C=C/CC1CCCC(=O)O1
• Description: 5-Hydroxy-7-decenoic acid δ-lactone has a coconut, fatty, fruity, peach, jasmine, woody, balsamic odor.

Technology Process of 2H-Pyran-2-one, tetrahydro-6-(2-pentenyl)-

There total 23 articles about 2H-Pyran-2-one, tetrahydro-6-(2-pentenyl)- 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: 90.0%

6-(2-pentynyl)-tetrahydro-2-pyranone (25448-66-2) → Jasmin lactone (25524-95-2,100428-67-9,68170-58-1)

Guidance literature:

With hydrogen; Lindlar's catalyst;

DOI:10.1246/cl.1983.911

Reference yield: 8.0%

2-<(Z)-2-pentenyl>cyclopentanone (42537-02-0,157357-32-9,157357-33-0,51608-18-5) → Jasmin lactone (25524-95-2,100428-67-9,68170-58-1) + (Z)-5-Hydroxy-dec-7-enoic acid (87611-61-8,173339-06-5,173339-07-6)

Guidance literature:

With bis-trimethylsilanyl peroxide; boron trifluoride diethyl etherate; In dichloromethane; at 25 ℃; for 4.5h;

DOI:10.1246/bcsj.56.2029

Reference yield:

1-bromo-pent-2-yne (16400-32-1) → Jasmin lactone (25524-95-2,100428-67-9,68170-58-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) LDA / 1.) THF, hexane, -10 deg C, 15 min, 2.) THF, hexane, -50 deg C, 6 h

2: Al₂O₃ / diethyl ether / 6 h / Ambient temperature

3: 99 percent / O₂, methylene blue / methanol / 3 h / 0 °C / Irradiation

4: NaBH₄, NaHCO₃ / H₂O / 2 h / Ambient temperature

5: p-TsOH / benzene / Heating

6: 90 percent / H₂, quinoline / 5percent Pd/BaSO₄ / benzene

With quinoline; aluminum oxide; sodium tetrahydroborate; hydrogen; oxygen; methylene blue; sodium hydrogencarbonate; toluene-4-sulfonic acid; lithium diisopropyl amide; Pd-BaSO₄; In methanol; diethyl ether; water; benzene;

DOI:10.1021/jo00356a035

upstream raw materials:

2-<(Z)-2-pentenyl>cyclopentanone

(Z)-5-Hydroxy-dec-7-enoic acid

6-(2-pentynyl)-tetrahydro-2-pyranone

2-((Z)-2-pentenyl)-3,4-dihydro-2H-pyran

Downstream raw materials:

(R)-(-)-jasmine lactone

(6S)-(+)-jasmine lactone

Refernces

• 1、 -. "Compounds having protected hydroxy groups". . . Retrieved 2008/06/13.
• 2、 -. "Beta-ketoester compounds". . . Retrieved 2008/06/13.