5-Norbornene-2,3-dicarboxylic acid, (1R,2S,3S,4S)-

Base Information

• Chemical Name: 5-Norbornene-2,3-dicarboxylic acid, (1R,2S,3S,4S)-
• CAS No.: 70190-87-3
• Molecular Formula: C₉H₁₀O₄
• Molecular Weight: 182.176
• UNII: 0EYF5B854O
• Nikkaji Number: J690.873J
• Wikidata: Q27236694

Synonyms:0EYF5B854O;UNII-0EYF5B854O;5-Norbornene-2,3-dicarboxylic acid, (-)-;5-Norbornene-2,3-dicarboxylic acid, (1R,2S,3S,4S)-;(1S,2S,3S,4R)-Bicyclo(2.2.1)hept-5-ene-2,3-dicarboxylic acid;Bicyclo(2.2.1)hept-5-ene-2,3-dicarboxylic acid, (1R,2S,3S,4S)-;Bicyclo(2.2.1)hept-5-ene-2,3-dicarboxylic acid, (1R-(2-endo,3-exo))-;70190-87-3;SCHEMBL1462211;(1R,2S,3S,4S)-5-norbornene-2,3-dicarboxylic acid;Q27236694

Chemical Property of 5-Norbornene-2,3-dicarboxylic acid, (1R,2S,3S,4S)-

Chemical Property:

• XLogP3: 0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 182.05790880
• Heavy Atom Count: 13
• Complexity: 266

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1C2C=CC1C(C2C(=O)O)C(=O)O
• Isomeric SMILES: C1[C@@H]2C=C[C@H]1[C@@H]([C@H]2C(=O)O)C(=O)O

Technology Process of 5-Norbornene-2,3-dicarboxylic acid, (1R,2S,3S,4S)-

There total 8 articles about 5-Norbornene-2,3-dicarboxylic acid, (1R,2S,3S,4S)- 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: 95.0%

(1S,2S,3S,4R)-Bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid bis-((R)-1-anthracen-9-yl-2,2,2-trifluoro-ethyl) ester (929108-82-7) → (R)-2,2,2-trifluoro-1-(9-anthryl)ethanol (53531-34-3,65487-67-4) + (1R,2S,3S,4S)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid (70190-87-3)

Guidance literature:

With potassium hydroxide; In tetrahydrofuran; water; for 4h;

DOI:10.1016/j.tetasy.2006.11.047

Reference yield: 72.0%

(2R,4S,8R)-2-((S)-hydroxy(quinolin-4-yl)methyl)-8-vinyl-1-azoniabicyclo[2.2.2]octane-(2S,3S)-3-carboxybicyclo[2.2.1]hept-5-ene-2-carboxylate → (+)-bicyclo[2.2.1]hept-5-ene-trans-2,3-dicarboxylic acid (1200-88-0,3813-52-3,3853-88-1,21196-51-0,32216-02-7,70095-09-9,70190-87-3)

Guidance literature:

With hydrogen bromide; In water;

DOI:10.1007/s10870-016-0640-4

Reference yield:

→ 5-norbornane-2,3-dicarboxylic acid (1200-88-0,3813-52-3,3853-88-1,21196-51-0,32216-02-7,70095-09-9,70190-87-3)

Guidance literature:

1,4-Endomethylen-cyclohex-5-en-endo,cis-2,3-dicarbonsaeureanhydrid, h. W.;

DOI:10.1007/BF00902103

upstream raw materials:

norbornene-5,6-dicarboxylic acid

(1S,2S,3S,4R)-Bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid bis-((R)-1-anthracen-9-yl-2,2,2-trifluoro-ethyl) ester

Downstream raw materials:

(1R,2R,3R,6S,7S,9S)-2-Hydroxy-5-oxo-4-oxa-tricyclo[4.2.1.0^3,7]nonane-9-carboxylic acid methyl ester

(1R,2R,3R,6S,7S,9R)-5-Oxo-2-phenylsulfanyl-4-oxa-tricyclo[4.2.1.0^3,7]nonane-9-carboxylic acid

(1R,2R,3R,6S,7S,9R)-5-Oxo-2-phenylsulfanyl-4-oxa-tricyclo[4.2.1.0^3,7]nonane-9-carboxylic acid amide

(1S,2S,3R,4R)-5-Benzenesulfonyl-3-carbamoyl-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester

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