(1R,​2S)​-​rel-1,​2-Cyclohexanedimethano​l

  • CAT Number: R025178
  • CAS Number: 15753-50-1
  • Molecular Formula: C8H16O2
  • Molecular Weight: 144.214
  • Purity: ≥95%
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Catalog Number R025178
CAS Number 15753-50-1
Molecular Formula

C8H16O2

Purity 95%
Storage -20°C
IUPAC Name [(1S,2R)-2-(hydroxymethyl)cyclohexyl]methanol
InChI InChI=1S/C8H16O2/c9-5-7-3-1-2-4-8(7)6-10/h7-10H,1-6H2/t7-,8+
InChIKey XDODWINGEHBYRT-OCAPTIKFSA-N
SMILES C1CCC(C(C1)CO)CO
Reference

[1]. van Bebber, J., Ahrens, H., Fr&ouml;hlich, R. and Hoppe, D., 1999.<br />
Efficient Desymmetrization of meso‐cis‐1, 2‐Cyclohexanedimethanol with Differentiation between Diastereotopic and Enantiotopic C&minus; H Bonds by (&minus;)‐Sparteine‐Mediated Deprotonation.<br />
Abstract: A powerful nonenzymatic desymmetrization of a meso-diol, coupled with an efficient diastereoselective C&ndash;C bond formation at one of the enantiotopic sites is reported. The key step consists of the selection by sec-butyllithium/(&minus;)-sparteine between enantiotopic and diastereotopic groups in the deprotonation step [Eq. (a)]. Kinetic resolutions of desymmetrized racemates (El = [D1] or Me3Sn) also were achieved.<br />
Chemistry&ndash;A European Journal, 5(6), pp.1905-1916.<br />
<br />
[2].YANG, C., HUANG, H., CHEN, L. and JI, T., 2017.<br />
Synthesis and Process Optimization of cis-1, 2-Cyclohexanedimethanol.<br />
Abstract: YANG, C., HUANG, H., CHEN, L. and JI, T., 2017. Synthesis and Process Optimization of cis-1, 2-Cyclohexanedimethanol. Journal of Hunan Institute of Science and Technology (Natural Sciences), p.04.<br />
Journal of Hunan Institute of Science and Technology (Natural Sciences), p.04.<br />
<br />
[3]. Nozaki, K., Yoshida, M. and Takaya, H., 1994.<br />
Reaction rate enhancement by addition of anionic surfactant SDS in the ruthenium catalyzed hydrogen transfer from a 1, 4-diol to 4-phenyl-3-buten-2-one.<br />
Abstract: Hydrogen transfer from cis-1,2-cyclohexanedimethanol to (E)-4-phenyl-3-buten-2-one catalyzed by [RuCl((S)-binap)(benzene)]Cl was accelerated by addition of SDS (sodium dodecyl sulfate). The long alkyl chain is essential for the enhancement of catalytic activity.<br />
Journal of organometallic chemistry, 473(1-2), pp.253-256.<br />
<br />
[4]. Huang, L., Romero, E., Ressmann, A.K., Rudroff, F., Hollmann, F., Fraaije, M.W. and Kara, S., 2017.<br />
Nicotinamide adenine dinucleotide‐dependent redox‐neutral convergent cascade for lactonizations with type II flavin‐containing monooxygenase.<br />
Abstract: A nicotinamide adenine dinucleotide (NADH)-dependent redox-neutral convergent cascade composed of a recently discovered type II flavin-containing monooxygenase (FMO&minus;E) and horse liver alcohol dehydrogenase (HLADH) has been established. Two model reaction cascades were analyzed for the synthesis of &gamma;-butyrolactone and chiral bicyclic lactones. In the former cascade, all substrates were converted into one single product &gamma;-butyrolactone with high atom efficiency. More than 130 mM &gamma;-butyrolactone were obtained when applying 100 mM cyclobutanone and 50 mM 1,4-butanediol in this cascade. In the second cascade where bicyclo[4.2.0]octan-7-one and cis-1,2-cyclohexanedimethanol were coupled, the ketone substrate was converted to the corresponding normal lactone with an ee value of 89&ndash;74% (3aS, 7aS) by FMO&minus;E alone and the abnormal lactone with an ee value of &gt;99% (3aR, 7aS) was formed by both HLADH and FMO&minus;E.<br />
Advanced Synthesis &amp; Catalysis, 359(12), pp.2142-2148.<br />
<br />
[5]. Sonmez, H.B., Karadag, K. and Onaran, G., 2011.<br />
Synthesis and swelling properties of crosslinked poly (orthosilicate) s from cyclohexanedimethanols.<br />
Abstract: Condensations of cyclohexanedimethanol derivatives with tetraethyl orthosilicate in the proper stoichiometric ratio produce crosslinked poly(orthosilicate)s. Synthesized crosslinked polymers have swelling abilities in common organic solvents such as tetrahydrofuran (THF), dichloromethane, benzene and acetone. All these polymers are moderately thermally stable and possess solvent uptake abilities that are not only good and fast but are also regenerable. FTIR, solid-state 13C, 29Si-NMR and thermal methods were used to characterize these synthesized polymers. The effects of different cyclohexanedimethanol derivatives on the properties of polymers were also examined. &copy; 2011 Wiley Periodicals, Inc. J Appl Polym Sci 122:1182&ndash;1189, 2011<br />
Journal of Applied Polymer Science, 122(2), pp.1182-1189.

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