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CS-W001157 4
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cis-endo-Bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid

  • CAS No. 3853-88-1

  • Cat. No. CS-0157298
  • Purity≥97%
  • MDL No.None

*For research and further manufacturing use only, not for direct human use.

cis-endo-Bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid|CS-0157298

Structure of 3853-88-1

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General Information

  • CAS No. 3853-88-1
  • Cat. No. CS-0157298
  • Purity ≥97%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₁₀O₄
  • Molecular Weight 182.17
  • Synonym(s) endo-Norbornene-cis-5,6-dicarboxylic acid
  • SMILES C1=C[C@@H]2C[C@H]1[C@@H]([C@@H]2C(=O)O)C(=O)O

Description

cis-endo-Bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid features a rigid, electron-deficient bicyclic framework with two carboxylic acid groups positioned for efficient cycloaddition reactions. This structure enables high diastereoselective [2+2] and [4+2] cycloadditions under mild conditions, making it ideal for constructing complex polycyclic architectures in synthetic organic chemistry and natural product synthesis.

Application

cis-endo-Bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid serves as a versatile Diels-Alder cycloaddition precursor and chiral building block in synthetic organic chemistry. Its rigid bicyclic framework provides defined stereochemistry, enabling predictable transformations in natural product synthesis and heterocycle construction. The molecule exhibits excellent bench stability, facilitates straightforward derivatization via esterification or amide formation, and functions effectively in standard coupling reactions due to its high functional group tolerance and clean reaction profiles.

Safety Information

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GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302+H312+H332-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P405-P501

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Computational Chemistry Data

  • TPSA   74.6
  • LogP   0.5939
  • H_Acceptors   2
  • H_Donors   2
  • Rotatable_Bonds   2

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