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cis-Dimethyl cyclohexane-1,4-dicarboxylate

  • CAS No. 3399-21-1

  • Cat. No. CS-0043139
  • Purity≥95%
  • MDL No.MFCD00216473

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

cis-Dimethyl cyclohexane-1,4-dicarboxylate|CS-0043139

Structure of 3399-21-1

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General Information

  • CAS No. 3399-21-1
  • Cat. No. CS-0043139
  • Purity ≥95%
  • MDL No. MFCD00216473
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₁₆O₄
  • Molecular Weight 200.23
  • Synonym(s) CIS-1,4-DIMETHYL CYCLOHEXANEDICARBOXYLATE
  • SMILES O=C([C@H]1CC[C@@H](C(OC)=O)CC1)OC

Description

cis-Dimethyl cyclohexane-1,4-dicarboxylate features a rigid, chair-conformationed cyclohexane core with both ester groups occupying equatorial positions. This stereochemical configuration enhances stability and facilitates predictable reactivity in asymmetric synthesis. The molecule serves as a key chiral scaffold for constructing complex cyclic architectures under standard conditions.

Application

cis-Dimethyl cyclohexane-1,4-dicarboxylate serves as a versatile chiral building block in synthetic organic chemistry, offering predictable stereochemical control due to its rigid cis-1,4-diaxial configuration. The molecule facilitates efficient functionalization at both carboxylate termini and supports transformations such as reduction, ester hydrolysis, and coupling reactions. Its bench-stable nature and compatibility with standard reaction conditions make it particularly useful for constructing cyclic scaffolds in natural product synthesis and medicinal chemistry campaigns.

Synthesis

  • Route1
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      1078-58-6
    • ~%
    • In-stock
      cis-Dimethyl cyclohexane-1,4-dicarboxylate|CS-0043139
      3399-21-1

    References

    • Takimoto; Mori Journal of the American Chemical Society, 2001 , vol. 123, # 12 p. 2895 - 2896
  • Route2
    • In-stock
      cis-Cyclohexane-1,4-dicarboxylic acid|CS-0042323
      619-81-8
    • null|null
      18107-18-1
    • ~%
    • In-stock
      cis-Dimethyl cyclohexane-1,4-dicarboxylate|CS-0043139
      3399-21-1

    References

    • Sankyo Company, Limited Patent: US5843973 A1, 1998 ;
  • Route3

    References

    • Kawai, Makoto; Sakurada, Isao; Morita, Asato; Iwamuro, Yuko; Ando, Kazuo; Omura, Hirofumi; Sakakibara, Sachiko; Masuda, Tsutomu; Koike, Hiroki; Honma, Teruki; Hattori, Kazunari; Takashima, Tadayuki; Mizuno, Kunihiko; Mizutani, Mayumi; Kawamura, Mitsuhiro Bioorganic and Medicinal Chemistry Letters, 2007 , vol. 17, # 20 p. 5537 - 5542

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   52.6
  • LogP   1.1388
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   2

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