2,5-Heptadienoic acid, 7-(2-(4-(3-chlorophenoxy)-3-hydroxy-1-butenyl)-3,5-dihydroxycyclopentyl)-, methyl ester, (1R-(1-alpha(2E,5E),2-beta(1E,3R*),3-alpha,5-alpha))-

Base Information

• Chemical Name: 2,5-Heptadienoic acid, 7-(2-(4-(3-chlorophenoxy)-3-hydroxy-1-butenyl)-3,5-dihydroxycyclopentyl)-, methyl ester, (1R-(1-alpha(2E,5E),2-beta(1E,3R*),3-alpha,5-alpha))-
• CAS No.: 68399-12-2
• Molecular Formula: C23H29ClO6
• Molecular Weight: 436.93
• Mol file: 68399-12-2.mol

Synonyms:2,5-Heptadienoic acid, 7-(2-(4-(3-chlorophenoxy)-3-hydroxy-1-butenyl)-3,5- dihydroxycyclopentyl)-, methyl ester, (1R-(1-alpha(2E,5E),2-beta(1E,3R*),3-alpha,5-alpha))-;68399-12-2;LS-74201

Chemical Property of 2,5-Heptadienoic acid, 7-(2-(4-(3-chlorophenoxy)-3-hydroxy-1-butenyl)-3,5-dihydroxycyclopentyl)-, methyl ester, (1R-(1-alpha(2E,5E),2-beta(1E,3R*),3-alpha,5-alpha))-

Chemical Property:

• Vapor Pressure: 6.9E-15mmHg at 25°C
• Boiling Point: 592.6°C at 760 mmHg
• Flash Point: 312.2°C
• PSA: 96.22000
• Density: 1.282g/cm³
• LogP: 3.05940
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 11
• Exact Mass: 436.1652663
• Heavy Atom Count: 30
• Complexity: 605

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C=CCC=CCC1C(CC(C1C=CC(COC2=CC(=CC=C2)Cl)O)O)O
• Isomeric SMILES: COC(=O)/C=C/C/C=C/CC1[C@H](C(CC1O)O)/C=C/[C@H](COC2=CC(=CC=C2)Cl)O

Technology Process of 2,5-Heptadienoic acid, 7-(2-(4-(3-chlorophenoxy)-3-hydroxy-1-butenyl)-3,5-dihydroxycyclopentyl)-, methyl ester, (1R-(1-alpha(2E,5E),2-beta(1E,3R*),3-alpha,5-alpha))-

There total 5 articles about 2,5-Heptadienoic acid, 7-(2-(4-(3-chlorophenoxy)-3-hydroxy-1-butenyl)-3,5-dihydroxycyclopentyl)-, methyl ester, (1R-(1-alpha(2E,5E),2-beta(1E,3R*),3-alpha,5-alpha))- 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:

(2E,5E)-7-[(1R,2R,3R,5S)-2-[(E)-(R)-4-(3-Chloro-phenoxy)-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3,5-bis-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hepta-2,5-dienoic acid methyl ester (69222-86-2) → 16-(3-chlorophenoxy)-17,18,19,20-tetranor-2,3-trans-5,6-trans-tetradehydroprostaglandin F1α methyl ester (68399-12-2)

Guidance literature:

With acetic acid; In tetrahydrofuran; at 70 ℃; for 0.333333h; Yield given;

DOI:10.1021/jm00179a011

Reference yield:

methyl (8R,9S,11R,12S,15S)-16-(m-chlorophenoxy)-9,11,15-trihydroxy-17,18,19,20-tetranor-5Z,13E-prostadienoate (56687-85-5) → 16-(3-chlorophenoxy)-17,18,19,20-tetranor-2,3-trans-5,6-trans-tetradehydroprostaglandin F1α methyl ester (68399-12-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 61 percent / diphenyl sulfide / methanol; benzene / 22 h / Irradiation

2: 95 percent / p-toluenesulfonic acid / CH₂Cl₂ / 0.25 h / 25 °C

3: 1.) LDA / 1.) THF, hexane, -78 deg C, 20 min, 2.) THF, hexane, a) -78 deg C, 30 min, b) 20 deg C, 30 min

4: 30percent H₂O₂ / ethyl acetate; methanol / 0.33 h / 40 °C

5: 65percent aq. acetic acid / tetrahydrofuran / 0.33 h / 70 °C

With diphenyl sulfide; dihydrogen peroxide; toluene-4-sulfonic acid; acetic acid; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; benzene;

DOI:10.1021/jm00179a011

Reference yield:

16-(3-chlorophenoxy)-17,18,19,20-tetranor-5,6-trans-didehydroprostaglandin F1α methyl ester 9,11,15-tris(tetrahydropyran-2-yl ether) (69222-88-4) → 16-(3-chlorophenoxy)-17,18,19,20-tetranor-2,3-trans-5,6-trans-tetradehydroprostaglandin F1α methyl ester (68399-12-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) LDA / 1.) THF, hexane, -78 deg C, 20 min, 2.) THF, hexane, a) -78 deg C, 30 min, b) 20 deg C, 30 min

2: 30percent H₂O₂ / ethyl acetate; methanol / 0.33 h / 40 °C

3: 65percent aq. acetic acid / tetrahydrofuran / 0.33 h / 70 °C

With dihydrogen peroxide; acetic acid; lithium diisopropyl amide; In tetrahydrofuran; methanol; ethyl acetate;

DOI:10.1021/jm00179a011

upstream raw materials:

(2E,5E)-7-[(1R,2R,3R,5S)-2-[(E)-(R)-4-(3-Chloro-phenoxy)-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3,5-bis-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hepta-2,5-dienoic acid methyl ester

methyl (8R,9S,11R,12S,15S)-16-(m-chlorophenoxy)-9,11,15-trihydroxy-17,18,19,20-tetranor-5Z,13E-prostadienoate

16-(3-chlorophenoxy)-17,18,19,20-tetranor-5,6-trans-didehydroprostaglandin F_1α methyl ester 9,11,15-tris(tetrahydropyran-2-yl ether)

(E)-7-[(1R,2R,3R,5S)-2-[(E)-(R)-4-(3-Chloro-phenoxy)-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3,5-bis-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-2-phenylselanyl-hept-5-enoic acid methyl ester

Refernces