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CS-W001157 4
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2,2-Dimethyl-5-(pyrrolidin-2-ylidene)-1,3-dioxane-4,6-dione

  • CAS No. 70912-52-6

  • Cat. No. CS-0165882
  • Purity≥97%
  • MDL No.None

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

2,2-Dimethyl-5-(pyrrolidin-2-ylidene)-1,3-dioxane-4,6-dione|CS-0165882

Structure of 70912-52-6

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General Information

  • CAS No. 70912-52-6
  • Cat. No. CS-0165882
  • Purity ≥97%
  • MDL No. None
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₁₃NO₄
  • Molecular Weight 211.21
  • Synonym(s) 2,2-dimethyl-5-pyrrolidin-2-ylidene-[1,3]dioxane-4.6-dione
  • SMILES O=C(/C1=C2NCCC/2)OC(C)(C)OC1=O

Description

This cyclic β-ketoester features a sterically hindered dimethyl substitution at the 2-position and a pyrrolidinylidene moiety at the 5-position, enhancing stability and modulating reactivity. The dioxane-dione core provides a rigid, electron-deficient scaffold ideal for Diels-Alder cycloadditions and heterocycle synthesis under mild conditions.

Application

2,2-Dimethyl-5-(pyrrolidin-2-ylidene)-1,3-dioxane-4,6-dione serves as a stable, bench-ready Michael acceptor and key building block for heterocyclic synthesis. Its α,β-unsaturated dione framework enables efficient conjugate addition with nucleophiles, facilitating the construction of complex pyrrolidine and piperidine scaffolds. The molecule exhibits excellent functional group tolerance and simplifies purification due to its crystalline nature, making it well-suited for iterative synthesis in medicinal chemistry and process development workflows.

Synthesis

  • Route1

    References

    • Fasseur, Dominique; Rigo, Benoit; Leduc, Catherine; Cauliez, Pascal; Couturier, Daniel Journal of Heterocyclic Chemistry, 1992 , vol. 29, # 5 p. 1285 - 1291
  • Route2
    • In-stock
      Pyrrolidine-2-thione|CS-W013703
      2295-35-4
    • null|null
      7270-63-5
    • ~45%
    • In-stock
      2,2-Dimethyl-5-(pyrrolidin-2-ylidene)-1,3-dioxane-4,6-dione|CS-0165882
      70912-52-6

    References

    • Koduri, Naga Durgarao; Scott, Halee; Hileman, Bethany; Cox, Justin D.; Coffin, Michael; Glicksberg, Lindsay; Hussaini, Syed R. Organic Letters, 2012 , vol. 14, # 2 p. 440 - 443
  • Route3
    • In-stock
      Pyrrolidine-2-thione|CS-W013703
      2295-35-4
    • 5-Bromo-2,2-dimethyl-1,3-dioxane-4,6-dione|CS-0322705
      66145-20-8
    • ~64%
    • In-stock
      2,2-Dimethyl-5-(pyrrolidin-2-ylidene)-1,3-dioxane-4,6-dione|CS-0165882
      70912-52-6

    References

    • Koduri, Naga Durgarao; Hileman, Bethany; Cox, Justin D.; Scott, Halee; Hoang, Phuong; Robbins, Alexa; Bowers, Kyle; Tsebaot, Lemma; Miao, Kun; Castaneda, Maria; Coffin, Michael; Wei, Guan; Claridge, Tim D. W.; Roberts, Kenneth P.; Hussaini, Syed Raziullah RSC Advances, 2013 , vol. 3, # 1 p. 181 - 188

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS05,GHS07
Signal Word : Danger
UN#: 3259
Class : 8
Packing Group : Ⅲ
Hazard Statements : H302-H315-H318-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   64.63
  • LogP   0.46
  • H_Acceptors   5
  • H_Donors   1
  • Rotatable_Bonds   0

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