3,4-Dehydro-L-proline

Name: 3,4-Dehydro-L-proline
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 4043-88-3
Cat. No. CS-W016613
Molecule weightNone
Purity≥95%
MDL No.MFCD00065964

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
Accessible (Haz class 3, 4, 5 or 8), International	$238.00+

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Structure of 4043-88-3

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General Information

CAS No. 4043-88-3
Cat. No. CS-W016613
Purity ≥95%
MDL No. MFCD00065964
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₅H₇NO₂
Molecular Weight None
Synonym(s) None
SMILES O=C(O)[C@H]1NCC=C1

Description

3,4-Dehydro-L-proline features a rigid, unsaturated pyrrolidine ring that enhances conformational control in peptide synthesis. This strained structure integrates readily into peptidomimetics, stabilizing bioactive conformations and improving metabolic resistance. Its electron-deficient double bond enables selective conjugate additions, streamlining access to complex heterocycles under mild conditions.

Application

3,4-Dehydro-L-proline serves as a versatile building block in peptide synthesis and medicinal chemistry, enabling the construction of constrained cyclic peptides and heterocyclic scaffolds. Its unsaturated pyrrolidine core facilitates stereoselective transformations and functions as a key intermediate in the synthesis of bioactive compounds. The compound exhibits bench stability and compatibility with standard coupling protocols, supporting efficient purification and integration into complex molecular architectures.

Synthesis

Route1
- 5211-24-5
- ~79%
- In-stock
  
  4043-88-3
References
- Rueeger, Heinrich; Benn, M. H. Canadian Journal of Chemistry, 1982 , vol. 60, p. 2918 - 2920
Route2
- 84062-30-6
- ~%
- In-stock
  
  4043-88-3
References
- Rueeger, Heinrich; Benn, M. H. Canadian Journal of Chemistry, 1982 , vol. 60, p. 2918 - 2920

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 49.33
LogP -0.401
H_Acceptors 2
H_Donors 2
Rotatable_Bonds 1

Other Classifications

Bioactive Molecules Peptides

Building Blocks Functional Group Carboxylic Acid

Building Blocks Skeleton Aliphatic heterocycle compounds Pyrroline compounds

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Life Science Amino Acids and their Derivatives Proline and derivatives

Chemical Biology Pharmaceutical Development and Drug Discovery Research Peptide Chemistry Amino Acid Derivatives

Chemical Biology Pharmaceutical Development and Drug Discovery Research Peptide Chemistry Unnatural Amino Acid Derivatives

Chemical Biology Pharmaceutical Development and Drug Discovery Research Reagents Peptide Chemistry Unnatural Amino Acid Derivatives

Chemical Biology Peptide Chemistry Amino Acid Derivatives

Biochemistry Biochemicals and Reagents Amino Acids non-Proteinogenic Amino Acids

Key Words

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3,4-Dehydro-L-proline

CAS No. 4043-88-3

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