Lot numbers can be found on the outside label of a product:
trans-2,5-Dioxopyrrolidin-1-yl 4-((2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)methyl)cyclohexanecarboxylate
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CAS No. 71875-81-5
- Cat. No. CS-0058807
- Purity≥96%
- MDL No.MFCD08274640
*For research and further manufacturing use only, not for direct human use.
Structure of 71875-81-5
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General Information
- CAS No. 71875-81-5
- Cat. No. CS-0058807
- Purity ≥96%
- MDL No. MFCD08274640
- Storage 4°C, stored under nitrogen
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₁₆H₁₈N₂O₆
- Molecular Weight 334.32
- Synonym(s) Cyclohexanecarboxylicacid, 4-[(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)methyl]-,2,5-dioxo-1-pyrrolidinyl ester, trans-
- SMILES O=C([C@H]1CC[C@H](CN2C(C=CC2=O)=O)CC1)ON3C(CCC3=O)=O
Description
This trans-2,5-dioxopyrrolidin-1-yl 4-((2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)methyl)cyclohexanecarboxylate features a sterically hindered cyclohexane core linked to a reactive pyrrolidinone ester. The pendant dioxopyrrolidinyl group enables efficient coupling under mild conditions, while the trans configuration ensures conformational rigidity. This structure delivers high reactivity and stability in amide bond formation workflows.
Application
trans-2,5-Dioxopyrrolidin-1-yl 4-((2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)methyl)cyclohexanecarboxylate serves as a robust activated ester for amide bond formation, enabling efficient coupling with amines under mild conditions. Its cyclohexanecarbonyl scaffold provides steric and electronic stability, while the pyrrolidinedione moiety enhances reactivity and facilitates purification. Functions reliably in peptide synthesis and macrocyclization workflows, offering high yield and compatibility with diverse functional groups.
Synthesis
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References
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Kimura, Sadaaki; Masunaga, Shin-Ichiro; Harada, Tomohiro; Kawamura, Yasuo; Ueda, Satoshi; Okuda, Kensuke; Nagasawa, Hideko Bioorganic and Medicinal Chemistry, 2011 , vol. 19, # 5 p. 1721 - 1728
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Route2
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69907-68-2 -
In-stock
5672-89-9 - ~89%
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In-stock
71875-81-5
References
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Paterson, Michael J.; Eggleston, Ian M. Synthetic Communications, 2008 , vol. 38, # 2 p. 303 - 308
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Route3
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69907-68-2
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In-stock
6066-82-6 - ~%
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In-stock
71875-81-5
References
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Leonard, Nicholas M.; Brunckova, Jarmila Journal of Organic Chemistry, 2011 , vol. 76, # 21 p. 9169 - 9174
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Safety Information
Download SDS|
GHS Pictogram :
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GHS No : GHS07
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Signal Word : Warning
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UN#: N/A
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Class : N/A
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Packing Group : N/A
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Hazard Statements : H315-H319-H335
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Precautionary Statements : P233-P261-P264-P271-P280-P302+P352-P304+P340-P362-P501
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Quality Control
Computational Chemistry Data
- TPSA 101.06
- LogP 0.325
- H_Acceptors 6
- H_Donors 0
- Rotatable_Bonds 4
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Key Words
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