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CS-W001157 4
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tert-Butyl trans-4-formylcyclohexylcarbamate

  • CAS No. 181308-57-6

  • Cat. No. CS-0047863
  • Purity≥95%
  • MDL No.MFCD03844598

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

tert-Butyl trans-4-formylcyclohexylcarbamate|CS-0047863

Structure of 181308-57-6

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General Information

  • CAS No. 181308-57-6
  • Cat. No. CS-0047863
  • Purity ≥95%
  • MDL No. MFCD03844598
  • Storage -20°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₂₁NO₃
  • Molecular Weight 227.30
  • Synonym(s) trans-tert-Butyl (4-formylcyclohexyl)carbamate
  • SMILES CC(C)(C)OC(=O)N[C@H]1CC[C@@H](CC1)C=O

Description

tert-Butyl trans-4-formylcyclohexylcarbamate features a rigid, conformationally defined cyclohexyl scaffold with a strategically positioned formyl group at the trans-4 position. This configuration enables precise spatial control in synthetic applications, while the carbamate moiety offers stability and convenient deprotection under mild conditions. The compound serves as a key intermediate in the construction of complex heterocycles and bioactive molecules.

Application

tert-Butyl trans-4-formylcyclohexylcarbamate serves as a versatile, bench-stable building block for the synthesis of functionalized cyclohexane scaffolds. The formyl group enables direct derivatization via nucleophilic addition, oxime formation, or reductive amination, while the carbamate protects the amine under standard reaction conditions. Its trans configuration ensures predictable stereochemical control in downstream transformations, facilitating access to complex heterocyclic and bioactive molecules with high regioselectivity.

Synthesis

  • Route1

    References

    • Zak, Mark; Hurley, Christopher A.; Ward, Stuart I.; Bergeron, Philippe; Barrett, Kathy; Balazs, Mercedesz; Blair, Wade S.; Bull, Richard; Chakravarty, Paroma; Chang, Christine; Crackett, Peter; Deshmukh, Gauri; Devoss, Jason; Dragovich, Peter S.; Eigenbrot, Charles; Ellwood, Charles; Gaines, Simon; Ghilardi, Nico; Gibbons, Paul; Gradl, Stefan; Gribling, Peter; Hamman, Chris; Harstad, Eric; Hewitt, Peter; Johnson, Adam; Johnson, Tony; Kenny, Jane R.; Koehler, Michael F. T.; Bir Kohli, Pawan; Labadie, Sharada; Lee, Wyne P.; Liao, Jiangpeng; Liimatta, Marya; Mendonca, Rohan; Narukulla, Raman; Pulk, Rebecca; Reeve, Austin; Savage, Scott; Shia, Steven; Steffek, Micah; Ubhayakar, Savita; Van Abbema, Anne; Aliagas, Ignacio; Avitabile-Woo, Barbara; Xiao, Yisong; Yang, Jing; Kulagowski, Janusz J. Journal of Medicinal Chemistry, 2013 , vol. 56, # 11 p. 4764 - 4785
  • Route2

    References

    • Journal of Medicinal Chemistry, , vol. 56, # 22 p. 9199 - 9221
  • Route3

    References

    • Journal of Medicinal Chemistry, , vol. 56, # 22 p. 9199 - 9221

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07,GHS09
Signal Word : Warning
UN#: 3077
Class : 9
Packing Group : Ⅲ
Hazard Statements : H400-H317
Precautionary Statements : P264-P273-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362+P364-P391-P501

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Computational Chemistry Data

  • TPSA   55.4
  • LogP   2.2688
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   2

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