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CS-W001157 4
Total: USD 88.00

3-((Benzyloxy)methyl)cyclobutanone

  • CAS No. 172324-67-3

  • Cat. No. CS-0051580
  • Purity≥96%
  • MDL No.MFCD09055138

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

3-((Benzyloxy)methyl)cyclobutanone|CS-0051580

Structure of 172324-67-3

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General Information

  • CAS No. 172324-67-3
  • Cat. No. CS-0051580
  • Purity ≥96%
  • MDL No. MFCD09055138
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₁₄O₂
  • Molecular Weight None
  • Synonym(s) None
  • SMILES O=C1CC(COCC2=CC=CC=C2)C1

Description

This cyclobutanone derivative features a benzyloxymethyl group that enhances solubility and facilitates selective functionalization. The carbonyl moiety enables efficient enolization and participation in Michael additions, while the benzyl protecting group allows for orthogonal deprotection under mild conditions.

Application

3-((Benzyloxy)methyl)cyclobutanone serves as a versatile synthetic intermediate for cyclobutane-based scaffolds, offering a bench-stable ketone functionality with orthogonal benzyloxy protection. It facilitates selective reductions, nucleophilic additions, and downstream functionalization in medicinal chemistry workflows. The benzyl ether group enables mild deprotection under hydrogenolysis conditions, supporting efficient late-stage modifications.

Synthesis

  • Route1
    • null|null
      172324-66-2
    • ~84%
    • In-stock
      3-((Benzyloxy)methyl)cyclobutanone|CS-0051580
      172324-67-3

    References

    • PFIZER LIMITED Patent: WO2006/92691 A1, 2006 ; Location in patent: Page/Page column 77-78 ;
  • Route2
    • null|null
      583830-08-4
    • ~57%
    • In-stock
      3-((Benzyloxy)methyl)cyclobutanone|CS-0051580
      172324-67-3

    References

    • Wager, Travis T.; Pettersen, Betty A.; Schmidt, Anne W.; Spracklin, Douglas K.; Mente, Scot; Butler, Todd W.; Howard, Harry; Lettiere, Daniel J.; Rubitski, David M.; Wong, Diane F.; Nedza, Frank M.; Nelson, Frederick R.; Rollema, Hans; Raggon, Jeffrey W.; Aubrecht, Jiri; Freeman, Jody K.; Marcek, John M.; Cianfrogna, Julie; Cook, Karen W.; James, Larry C.; Chatman, Linda A.; Iredale, Philip A.; Banker, Michael J.; Homiski, Michael L.; Munzner, Jennifer B.; Chandrasekaran, Rama Y. Journal of Medicinal Chemistry, 2011 , vol. 54, # 21 p. 7602 - 7620
  • Route3
    • In-stock
      ((Allyloxy)methyl)benzene|CS-0157968
      14593-43-2
    • null|null
      76-02-8
    • ~%
    • In-stock
      3-((Benzyloxy)methyl)cyclobutanone|CS-0051580
      172324-67-3

    References

    • Eisai RandD Management Co., Ltd. Patent: US2011/86882 A1, 2011 ; Location in patent: Page/Page column 23 ; US 20110086882 A1

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   26.3
  • LogP   2.1823
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   4

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