1H-Indene-2-carboxylic acid, 1-(1,3-benzodioxol-5-yl)-3-(2-(carboxymethoxy)-4-methoxyphenyl)-2,3-dihydro-5-propoxy-, (1S,2R,3S)-

Base Information

• Chemical Name: 1H-Indene-2-carboxylic acid, 1-(1,3-benzodioxol-5-yl)-3-(2-(carboxymethoxy)-4-methoxyphenyl)-2,3-dihydro-5-propoxy-, (1S,2R,3S)-
• CAS No.: 157659-79-5
• Molecular Formula: C₂₉H₂₈O₉
• Molecular Weight: 520.536
• UNII: 0I32BCL40Z
• DSSTox Substance ID: DTXSID00935762
• Nikkaji Number: J597.682K
• Wikidata: Q27088700
• Pharos Ligand ID: Q7G2V611CDDP
• ChEMBL ID: CHEMBL8823
• Mol file: 157659-79-5.mol

Synonyms:1H-Indene-2-carboxylic acid, 1-(1,3-benzodioxol-5-yl)-3-(2- (carboxymethoxy)-4-methoxyphenyl)-2,3-dihydro-5-propoxy-, (1S,2R,3S)-;3-(2-(carboxymethoxy)-4-methoxyphenyl)-1-(3,4-(methylenedioxy)phenyl)-5-(prop-1-yloxy)indan-2-carboxylic acid;SB 209670;SB-209670

Chemical Property of 1H-Indene-2-carboxylic acid, 1-(1,3-benzodioxol-5-yl)-3-(2-(carboxymethoxy)-4-methoxyphenyl)-2,3-dihydro-5-propoxy-, (1S,2R,3S)-

Chemical Property:

• Vapor Pressure: 7.51E-21mmHg at 25°C
• Boiling Point: 704.8°C at 760 mmHg
• Flash Point: 233.3°C
• Density: 1.346g/cm³
• XLogP3: 4.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 10
• Exact Mass: 520.17333247
• Heavy Atom Count: 38
• Complexity: 820

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCCOC1=CC2=C(C=C1)C(C(C2C3=C(C=C(C=C3)OC)OCC(=O)O)C(=O)O)C4=CC5=C(C=C4)OCO5
• Isomeric SMILES: CCCOC1=CC2=C(C=C1)[C@@H]([C@H]([C@@H]2C3=C(C=C(C=C3)OC)OCC(=O)O)C(=O)O)C4=CC5=C(C=C4)OCO5

Technology Process of 1H-Indene-2-carboxylic acid, 1-(1,3-benzodioxol-5-yl)-3-(2-(carboxymethoxy)-4-methoxyphenyl)-2,3-dihydro-5-propoxy-, (1S,2R,3S)-

There total 23 articles about 1H-Indene-2-carboxylic acid, 1-(1,3-benzodioxol-5-yl)-3-(2-(carboxymethoxy)-4-methoxyphenyl)-2,3-dihydro-5-propoxy-, (1S,2R,3S)- 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: 81.0%

(+)Methyl-(1S,2S,3S)-3-(2-Carboethoxymethoxy-4-methoxyphenyl)-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indane-2-carboxylate (156129-15-6) → (+)-(1S,2R,3S)-1-(3,4-methylenedioxyphenyl)-3-[2-(carboxymethoxy)-4-methoxyphenyl]-2,3-dihydro-5-(prop-1-yloxy)-1H-indene-2-carboxylic acid (157659-79-5)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; water;

Reference yield:

3-Hydroxyacetophenone (121-71-1) → (+)-(1S,2R,3S)-1-(3,4-methylenedioxyphenyl)-3-[2-(carboxymethoxy)-4-methoxyphenyl]-2,3-dihydro-5-(prop-1-yloxy)-1H-indene-2-carboxylic acid (157659-79-5)

Guidance literature:

Multi-step reaction with 10 steps

1: 100 percent / K₂CO₃ / dimethylformamide

2: 100 percent / NaH

3: 48 percent / piperidine, acetic acid / benzene / Heating

4: 87 percent / TFA

5: 44 percent / DDQ / dioxane

6: 91 percent / diethyl ether

7: 96 percent / H₂ / 10percent Pd/C / ethanol; ethyl acetate / 50 °C / 2585.7 Torr

8: 78 percent / aq. HCl / methanol

9: 71 percent / NaH / dimethylformamide

10: 1.) aq. NaOH, 2.) aq. HCl / 1.) dioxane

With piperidine; hydrogenchloride; sodium hydroxide; hydrogen; sodium hydride; potassium carbonate; acetic acid; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium on activated charcoal; In 1,4-dioxane; methanol; diethyl ether; ethanol; ethyl acetate; N,N-dimethyl-formamide; benzene;

DOI:10.1021/jm00037a003

Reference yield:

3-(prop-1-yloxy)acetophenone (121704-77-6) → (+)-(1S,2R,3S)-1-(3,4-methylenedioxyphenyl)-3-[2-(carboxymethoxy)-4-methoxyphenyl]-2,3-dihydro-5-(prop-1-yloxy)-1H-indene-2-carboxylic acid (157659-79-5)

Guidance literature:

Multi-step reaction with 9 steps

1: 100 percent / NaH

2: 48 percent / piperidine, acetic acid / benzene / Heating

3: 87 percent / TFA

4: 44 percent / DDQ / dioxane

5: 91 percent / diethyl ether

6: 96 percent / H₂ / 10percent Pd/C / ethanol; ethyl acetate / 50 °C / 2585.7 Torr

7: 78 percent / aq. HCl / methanol

8: 71 percent / NaH / dimethylformamide

9: 1.) aq. NaOH, 2.) aq. HCl / 1.) dioxane

With piperidine; hydrogenchloride; sodium hydroxide; hydrogen; sodium hydride; acetic acid; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium on activated charcoal; In 1,4-dioxane; methanol; diethyl ether; ethanol; ethyl acetate; N,N-dimethyl-formamide; benzene;

DOI:10.1021/jm00037a003

upstream raw materials:

(1S,2S,3S)-1-Benzo[1,3]dioxol-5-yl-3-(4-methoxy-2-methoxycarbonylmethoxy-phenyl)-5-propoxy-indan-2-carboxylic acid methyl ester

piperonal

1-(2-Bromo-5-propoxyphenyl)ethanone

3-(1,3-benzodioxol-5-yl)-6-propoxy-1H-inden-1-one

Refernces

• 1、 Clark, William M.,Tickner-Eldridge, Ann M.,Kris Huang,Pridgen, Lendon N.,Olsen, Mark A.,Mills, Robert J.,Lantos, Ivan,Baine, Neil H.. "A catalytic enantioselective synthesis of the endothelin receptor antagonists SB-209670 and SB-217242. A base-catalyzed stereospecific formal 1,3-hydrogen transfer of a chiral 3-arylindenol". . p. 4550 - 4551. Retrieved 2007/10/03.
• 2、 -. "ENDOTHELIN RECEPTOR ANTAGONISTS". . . Retrieved 2008/06/13.