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1072-86-2 Usage

Chemical Properties

white to off-white crystals

Check Digit Verification of cas no

The CAS Registry Mumber 1072-86-2 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,0,7 and 2 respectively; the second part has 2 digits, 8 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 1072-86:
(6*1)+(5*0)+(4*7)+(3*2)+(2*8)+(1*6)=62
62 % 10 = 2
So 1072-86-2 is a valid CAS Registry Number.
InChI:InChI=1/C6H12O2/c7-5-3-1-2-4-6(5)8/h5-8H,1-4H2/t5-,6-/m1/s1

1072-86-2 Well-known Company Product Price

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  • Aldrich

  • (421790)  (1R,2R)-trans-1,2-Cyclohexanediol  99%

  • 1072-86-2

  • 421790-1G

  • 3,279.51CNY

  • Detail

1072-86-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name (1R,2R)-cyclohexane-1,2-diol

1.2 Other means of identification

Product number -
Other names 1R,2R-cyclohexanediol

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1072-86-2 SDS

1072-86-2Relevant articles and documents

Asymmetric trans-dihydroxylation of cyclic olefins by enzymatic or chemo-enzymatic sequential epoxidation and hydrolysis in one-pot

Xu, Yi,Li, Aitao,Jia, Xin,Li, Zhi

, p. 2452 - 2458 (2011)

Novel and efficient one-pot enzymatic and chemo-enzymatic synthetic methods are developed for the asymmetric trans-dihydroxylations of cyclic olefins 1a and 1bvia sequential epoxidation and hydrolysis. The Novozym 435 -mediated epoxidation of cyclohexene 1a and subsequent hydrolysis of the intermediate cyclohexene oxide 2a with resting cells of Sphingomonas sp. HXN-200 in one-pot gave (1R,2R)-cyclohexane diol 3a in 84% ee and 95% conversion. trans-Dihydroxylation of N-benzyloxycarbonyl 3-pyrroline 1b with the same enzymatic system gave the corresponding (3R,4R)-N- benzyloxycarbonyl-3,4-dihydroxy-pyrrolidine 3b in 93% ee and 94% conversion. In the one-pot chemo-enzymatic system, epoxidation of N-benzyloxycarbonyl 3-pyrroline 1b by m-CPBA and subsequent hydrolysis of epoxide intermediate 2b with resting cells of Sphingomonas sp. HXN-200 gave the trans-diol (3R,4R)-3b in 92% ee and 94-97% conversion. While the trans-dihydroxylation of cyclohexene 1a to (1R,2R)-cyclohexane diol 3a is reported for the first time, the trans-dihydroxylation of N-benzyloxycarbonyl 3-pyrroline 1b to (3R,4R)-3b with such an enzymatic or chemo-enzymatic system afforded a much higher product concentration than the same reaction with the system using a microorganism containing the two necessary enzymes. The developed one-pot enzymatic and chemo-enzymatic systems for the asymmetric trans-dihydroxylation of olefins are new, easy to prepare, adjust and operate, are high yielding, complementary to Sharpless asymmetric dihydroxylation and particularly useful for the asymmetric synthesis of cyclic trans-diols.

Enantioselective Ester Hydrolyses Employing Rhizopus nigricans. A Method of Preparing and Assigning the Absolute Stereochemistry of Cyclic Alcohols

Kasai, Masaji,Kawai, Ken-ichi,Imuta, Mitsuru,Ziffer, Herman

, p. 675 - 679 (1984)

The mold Rhizopus nigricans has been used to hydrolyze enantioselectively the acetates of several series of benzocycloalken-3-ols and 2-substituted cycloalkanols to yield chiral alcohols.The configurations of the alcohols formed were established.The absolute stereochemistries of 25 of the 26 alcohols obtained were found to conform to a generalization based on the effective sizes of substituents on the carbinol carbon.The relative sizes of substituents required for agreement were identical with those employed in Horeu's method of establishing the absolute stereochemistry of the same compounds.The use of these microbially mediated hydrolyses to assign the absolute stereochemistry of cyclic secondary alcohols is compared to Horeau's method and to the use of empirical relations between the absolute stereochemistry of an enantiomer and the order, relative to its antipode, in which it is eluted from a chiral (Pirkle) column.

Bunton,Carr

, p. 770,774 (1963)

Selective electrochemical reduction of cinnamyl ethers in the presence of other allylic C-O bonds

Solis-Oba, Aida,Hudlicky, Tomas,Koroniak, Lukasz,Frey, Dean

, p. 1241 - 1243 (2001)

Several conduritol derivatives protected as allyl and cinnamyl ethers were subjected to electrochemical reduction at a mercury cathode, resulting in selective removal of the cinnamyl group.

Highly enantioselective hydrolysis of alicyclic meso-epoxides with a bacterial epoxide hydrolase from Sphingomonas sp. HXN-200: Simple syntheses of alicyclic vicinal trans-diols

Chang, Dongliang,Wang, Zunsheng,Heringa, Maarten F.,Wirthner, Renato,Witholt, Bernard,Li, Zhi

, p. 960 - 961 (2003)

Hydrolysis of N-benzyloxycarbonyl-3,4-epoxy-pyrrolidine and cyclohexene oxide with the epoxide hydrolase of Sphingomonas sp. HXN-200, respectively, gave the corresponding vicinal trans-diols in high ee and yield, representing the first example of enantioselective hydrolysis of a meso-epoxide with a bacterial epoxide hydrolase.

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Freppel et al.

, p. 2586 (1971)

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Epoxidation of cyclohexene with H2O2 over efficient water-tolerant heterogeneous catalysts composed of mono-substituted phosphotungstic acid on co-functionalized SBA-15

Jin, Manman,Niu, Qingtao,Guo, Zhenmei,Lv, Zhiguo

, (2019)

A series of Keggin-type heteropolyacid-based heterogeneous catalysts (Co-/Fe-/Cu-POM-octyl-NH3-SBA-15) were synthesized via immobilized transition metal mono- substituted phosphotungstic acids (Co-/Fe-/Cu-POM) on octyl-amino-co-functionalized mesoporous silica SBA-15 (octyl-NH2-SBA-15). Characterization results indicated that Co-/Fe-/Cu-POM units were highly dispersed in mesochannels of SBA-15, and both types of Br?nsted and Lewis acid sites existed in Co-/Fe-/Cu-POM-octyl-NH3-SBA-15 catalysts. Co-POM-octyl-NH3-SBA-15 catalyst showed excellent catalytic performance in H2O2-mediated cyclohexene epoxidation with 83.8% of cyclohexene conversion, 92.8% of cyclohexene oxide selectivity, and 98/2 of epoxidation/allylic oxidation selectivity. The order of catalytic activity was Co-POM-octyl-NH3-SBA-15?>?Fe-POM-octyl-NH3-SBA-15?>?Cu-POM-octyl-NH3-SBA-15. In order to obtain insights into the role of -octyl moieties during catalysis, an octyl-free catalyst (Co-POM-NH3-SBA-15) was also synthesized. In comparison with Co-POM-NH3-SBA-15, Co-POM-octyl-NH3-SBA-15 showed enhanced catalytic properties (viz. activity and selectivity) in cyclohexene epoxidation. Strong chemical bonding between -NH3 + anchored on the surface of SBA-15 and heteropolyanions resulted in excellent stability of Co-POM-octyl-NH3-SBA-15 catalyst, and it could be reused six times without considerable loss of activity.

STEREOSPECIFIC PREPARATION OF MONOGLUCOSIDES OF OPTICALY ACTIVE trans-1,2-CYCLOHEXANEDIOLS BY ENZYMIC TRANS-D-GLUCOSYLATION, AND (13)C-N.M.R. SPECTROSCOPY OF THE RESULTING MONO-D-GLUCOPYRANOSIDES

Itano, Kayoko,Yamasaki, Kazuo,Kihara, Chikako,Tanaka, Osamu

, p. 27 - 34 (1980)

Anomeric mono-D-glucosides of optically active trans-1,2-cyclohexanediols were stereoselectively prepared from the racemic mixture by means of enzymic trans-D-glucosylation using crude enzyme preparations that are commercially available or are utilized for food manufacturing.The (13)C-n.m.r. spectra of these D-glucosides were characterized, and the stereochemical influence, on the glycosylation shifts of cyclohexanol, of the vicinal hydroxyl substitution was discussed in comparison with that of vicinal alkyl substitution reported previously.

Mixing and matching chiral cobalt- and manganese-based calix-salen catalysts for the asymmetric hydrolytic ring opening of epoxides

Dandachi, Hiba,Zaborova, Elena,Kolodziej, Emilie,David, Olivier R.P.,Hannedouche, Jér?me,Mellah, Mohamed,Jaber, Nada,Schulz, Emmanuelle

, p. 246 - 253 (2016)

Homochiral oligomeric salen macrocycles possessing aromatic spacers have been prepared as new calix-salen derivatives. The corresponding cobalt and manganese complexes were synthesized and characterized, and their catalytic activities have been studied in the challenging hydrolysis of meso epoxides. While manganese calix-salen complexes were not active in the studied reactions, the dual heterobimetallic system, using an equimolar combination of cobalt and manganese calix-salen derivatives proved to be more enantioselective than the sole cobalt system. Furthermore, as heterogeneous complexes, the catalytic mixture could be easily recovered by simple filtration and successfully reengaged in subsequent catalytic runs. Interestingly, no need for cobalt reactivation was noticed to maintain maximum efficiency of this dual system. The matched Co/Mn dual catalyst was also used to promote the dynamic hydrolytic kinetic resolution of epibromohydrin.

Structure-Guided Triple-Code Saturation Mutagenesis: Efficient Tuning of the Stereoselectivity of an Epoxide Hydrolase

Sun, Zhoutong,Lonsdale, Richard,Wu, Lian,Li, Guangyue,Li, Aitao,Wang, Jianbo,Zhou, Jiahai,Reetz, Manfred T.

, p. 1590 - 1597 (2016)

The directed evolution of enzymes promises to eliminate the long-standing limitations of biocatalysis in organic chemistry and biotechnology - the often-observed limited substrate scope, insufficient activity, and poor regioselectivity or stereoselectivity. Saturation mutagenesis at sites lining the binding pocket with formation of focused libraries has emerged as the technique of choice, but choosing the optimal size of the randomization site and reduced amino acid alphabet for minimizing the labor-determining screening effort remains a challenge. Here, we introduce structure-guided triple-code saturation mutagenesis (TCSM) by encoding three rationally chosen amino acids as building blocks in the randomization of large multiresidue sites. In contrast to conventional NNK codon degeneracy encoding all 20 canonical amino acids and requiring the screening of more than 1015 transformants for 95% library coverage, TCSM requires only small libraries not exceeding 200-800 transformants in one library. The triple code utilizes structural (X-ray) and consensus-derived sequence data, and is therefore designed to match the steric and electrostatic characteristics of the particular enzyme. Using this approach, limonene epoxide hydrolase has been successfully engineered as stereoselective catalysts in the hydrolytic desymmetrization of meso-type epoxides with formation of either (R,R)- or (S,S)-configurated diols on an optional basis and kinetic resolution of chiral substrates. Crystal structures and docking computations support the source of notably enhanced and inverted enantioselectivity.

Optically active polycarbonates: Asymmetric alternating copolymerization of cyclohexene oxide and carbon dioxide [4]

Nozaki, Kyoko,Nakano, Koji,Hiyama, Tamejiro

, p. 11008 - 11009 (1999)

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Heterobimetallic dual-catalyst systems for the hydrolytic kinetic resolution of terminal epoxides

Hong, Xiang,Mellah, Mohamed,Schulz, Emmanuelle

, p. 2608 - 2617 (2014)

A heterobimetallic dual-catalyst system based on the preparation and use of various salen complexes has been developed for the hydrolytic kinetic resolution (HKR) of terminal epoxides. A combination of cobalt-salen and manganese-salen complexes, generated from ligands with the same configuration possessing thiophene or pyrrole moieties, produced indeed highly selective catalysts for the hydrolysis of epibromohydrin. This effect could also be extended to other terminal epoxides and to the more challenging ring opening of cyclohexene oxide. Kinetic studies indicated that only one CoIII salen complex was involved in the rate-determining step, which supported a heterobimetallic highly enantioselective pathway based on the crucial existence of in situ generated CoIII-OH species, previously postulated in the literature. The beneficial effect of the presence of additional Mn-complexes was ascribed to the inhibition of the alternative less enantioselective monometallic reaction pathway by epoxide activation.

Kinetic resolution of vic-diols by Bacillus stearothermophilus diacetyl reductase

Bortolini, Olga,Casanova, Elena,Fantin, Giancarlo,Medici, Alessandro,Poli, Silvia,Hanau, Stefania

, p. 647 - 651 (1998)

The kinetic resolution of several racemic syn- and anti-1,2-diols by enzymatic oxidation with Bacillus stearothermophilus diacetyl reductase is described. The enantiomerically pure (R,R)- and (R,S)-diols are recovered in almost quantitative yield.

Enantiotopic Discrimination by Coordination-Desymmetrized meso-Ligands

Li, Yutang,Lidskog, Anna,Armengol-Relats, Helena,Pham, Thanh Huong,Favraud, Antoine,Nicolas, Maxime,Dawaigher, Sami,Xiao, Zeyun,Ma, Dayou,Lindb?ck, Emil,Strand, Daniel,W?rnmark, Kenneth

, p. 1575 - 1579 (2020)

The first examples of enantiopure catalysts that are chiral merely due to coordination of different metal ions at enantiotopic positions of an achiral meso-ligand are reported. These catalysts exhibit a pseudo-Cs symmetry and are able to catalyze reactions demanding simultaneous involvement of two catalytic sites. The latter was demonstrated by application in the asymmetric ring-opening of meso-epoxides.

Highly Enantioselective Catalytic System for Asymmetric Copolymerization of Carbon Dioxide and Cyclohexene Oxide

Hua, Yuan-Zhao,Lu, Liu-Jie,Huang, Pei-Jin,Wei, Dong-Hui,Tang, Ming-Sheng,Wang, Min-Can,Chang, Jun-Biao

, p. 12394 - 12398 (2014)

A new ligand can be easily prepared, and its intramolecular dinuclear zinc complexes act as a high performance catalyst for the asymmetric alternating copolymerization of cyclohexene oxide and CO2under very mild conditions (1 atm CO2, room temperature), affording completely alternating polycarbonates with up to 93.8 % enantiomeric excess (ee) and 98 % yield. A high Mnvalue of 28 600 and a relatively narrow polydispersity (Mw/Mnratio) of 1.43 were also achieved.

Enantioselective hydrolysis of aryl, alicyclic and aliphatic epoxides by Rhodotorula glutinis

Weijers, Carel A. G. M.

, p. 639 - 647 (1997)

Enantioselective epoxide hydrolysis by yeasts has been demonstrated for the hydrolysis of several aryl, alicyclic and aliphatic epoxides by a strain of Rhodotorula glutinis. High enantioselectivity was obtained in the hydrolysis of methyl substituted aryl and aliphatic epoxides whereas selectivity towards terminal epoxides in all cases was lower. Homochiral vicinal diols were formed from several methyl substituted epoxides and also from meso epoxides. Kinetic resolution of trans-1-phenyl-1,2-epoxypropane was studied in more detail.

Wynberg,Kraak

, p. 3919 (1961)

Tris[Trinitrato Ce(IV)]paraperiodate, an efficient heterogeneous catalyst for alcoholysis, acetolysis and hydrolysis of epoxides

Iranpoor,Zardaloo

, p. 1959 - 1969 (1994)

Tristrinitrato [Ce(IV)]paraperiodate (TTCPP) catalyses ring opening of epoxides in alcohols and water stereo- and regioselectively and under heterogeneous conditions to produce the corresponding β-alkoxy alcohols and 1,2 diols respectively in good to high yields. In acetic acid, ring opening and dimerization of epoxides occurs with this catalyst to produce the corresponding succinic acid derivatives in high yields.

Asymmetric hydrogenation of cyclohexane-1,2-dione over cinchonidine-modified platinum

Sonderegger, Otmar J.,Buergi, Thomas,Baiker, Alfons

, p. 116 - 121 (2003)

The asymmetric hydrogenation of cyclohexane-1,2-dione over cinchonidine-modified platinum was investigated. Despite the fact that the first hydrogenation step is close to nonenantioselective, a high enantiomeric excess is obtained for the (R)-α-hydroxyketone due to kinetic resolution. In the second hydrogenation step one out of the four reactions of the network is substantially accelerated with respect to the others and with respect to the reaction in the absence of modifier, leading to an enantiomeric excess of (1R,2R)-trans-cyclohexane-1,2-diol of over 80%. Comparison with recently reported asymmetric hydrogenation of α-hydroxyethers indicates striking similarities, which hint at similar reactant-modifier interaction in both cases. The importance of cis versus trans conformation of the reactant for the reactant-modifier interaction emerges from a comparison of suggested reaction intermediates for cyclohexane-1,2-dione and butane-2,3-dione hydrogenation, respectively.

Enantioselective biooxidation of racemic trans-cyclic vicinal diols: One-pot synthesis of both enantiopure (S,S)-cyclic vicinal diols and (R)-α-hydroxy ketones

Zhang, Jiandong,Xu, Tingting,Li, Zhi

, p. 3147 - 3153 (2013)

Highly regio- and enantioselective alcohol dehydrogenases BDHA (2,3-butanediol dehydrogenase from Bacillus subtilis BGSC1A1), CDDHPm (cyclic diol dehydrogenase from Pseudomonas medocina TA5), and CDDHRh (cyclic diol dehydrogenase from Rhodococcus sp. Moj-3449) were discovered for the oxidation of racemic trans-cyclic vicinal diols. Recombinant Escherichia coli expressing BDHA was engineered as an efficient whole-cell biocatalyst for the oxidation of (±)-1,2-cyclopentanediol, 1,2-cyclohexanediol, 1,2-cycloheptane-diol, and 1,2-cyclooctanediol, respectively, to give the corresponding (R)-α-hydroxy ketones in >99% ee and (S,S)-cyclic diols in >99% ee at 50% conversion in one pot. Escherichia coli (BDHA-LDH) co-expressing lactate dehydrogenase (LDH) for intracellular regeneration of NAD+ catalyzed the regio- and enantioselective oxidation of (±)-1,2-dihydroxy-1,2,3,4- tetrahydronaphthalene to produce the corresponding (R)-α-hydroxy ketone in >99% ee and (S,S)-cyclic diol in 96% ee at 49% conversion. Preparative biotransformations were also demonstrated. Thus, a novel and useful method for the one-pot synthesis of both vicinal diols and α-hydroxy ketones in high ee was developed via high Copyright

Bergbreiter,Killough

, p. 2126,2128, 2132, 2133 (1978)

Phenolic glycosides from the twigs of Salix glandulosa

Kim, Chung Sub,Kwon, Oh Wook,Kim, Sun Yeou,Choi, Sang Un,Kim, Jae Yoon,Han, Ji Young,Choi, Soo Im,Choi, Jong Gil,Kim, Ki Hyun,Lee, Kang Ro

, p. 1955 - 1961 (2014)

As a part of an ongoing search for bioactive constituents from Korean medicinal plants, the phytochemical investigations of the twigs of Salix glandulosa afforded 12 new phenolic glycosides (1-12) and a known analogue (13). The structures of 1-13 were characterized by a combination of NMR methods (1H and 13C NMR, 1H-1H COSY, HMQC, and HMBC), chemical hydrolysis, and GC/MS. The absolute configuration of 13 [(1R,2S)-2-hydroxycyclohexyl-2′-O-trans-p-coumaroyl-β-d- glucopyranoside] was determined for the first time. Compounds 1-3, 6, and 7 exhibited inhibitory effects on nitric oxide production in lipopolysaccharide- activated murine microglial cells (IC50 values in the range 6.6-20.5 μM).

Groves,Swanson

, p. 1953,1954 (1975)

Enantioselective Cascade Biocatalysis via Epoxide Hydrolysis and Alcohol Oxidation: One-Pot Synthesis of (R)-α-Hydroxy Ketones from Meso- or Racemic Epoxides

Zhang, Jiandong,Wu, Shuke,Wu, Jinchuan,Li, Zhi

, p. 51 - 58 (2015)

A new type of cascade biocatalysis was developed for one-pot enantioselective conversion of a meso- or racemic epoxide to an α-hydroxy ketone in high ee via an epoxide hydrolase-catalyzed hydrolysis of the epoxide, an alcohol dehydrogenase-catalyzed oxidation of the diol intermediate, and an enzyme-catalyzed cofactor regeneration. In vitro cascade biotransformation of meso-epoxides (cyclopentene oxide 1a, cyclohexene oxide 1b, and cycloheptene oxide 1c) was achieved with cell-free extracts containing recombinant SpEH (epoxide hydrolase from Sphingomonas sp. HXN-200), BDHA (butanediol dehydrogenase from Bacillus subtilis BGSC1A1), and LDH (lactate dehydrogenase form Bacillus subtilis) or NOX (NADH oxidase from Lactobacillus brevis DSM 20054), respectively, giving the corresponding (R)-α-hydroxycyclopentanone 3a, (R)-α-hydroxycyclohexanone 3b, and (R)-α-hydroxycycloheptanone 3c in 98-99% ee and 70-50% conversion with TTN of NAD+-recycling of 5500-26000. Cascade catalysis with mixed cells of Escherichia coli (SpEH) and E. coli (BDHA-NOX) converted 100-300 mM meso-epoxides 1a-1c to (R)-α-hydroxy ketones 3a-3c in 98-99% ee and 85-57% conversion. Cells of E. coli (SpEH-BDHA-NOX) coexpressing all three enzymes were also proven as good catalysts for the cascade conversion of 100-200 mM meso-epoxides 1a-1c, giving (R)-α-hydroxy ketones 3a-3c in 98-99% ee and 79-52% conversion. The cascade biocatalysis for one-pot synthesis of α-hydroxy ketone in high ee was also successfully demonstrated with a racemic epoxide (1,2,3,4-tetrahydronaphthalene-1,2-oxide 1d) as the substrate. By using two whole-cells based approaches, (R)-α-hydroxytetralone 3d was obtained in 99% ee and 49-40% conversion from 20 to 5 mM racemic epoxide 1d. Preparative cascade biotransformation of cyclohexene oxide 1b gave (R)-α-hydroxycyclohexanone 3b in 98% ee with 70% isolated yield. The developed new type of cascade biocatalysis is enantioselective, green, and often high yielding. The concept might be generally applicable to produce other useful enantiopure α-hydroxy ketones from the corresponding meso- or racemic epoxides by cascade catalysis using appropriate enzymes. (Chemical Equation Presented).

Olefin reaction in the catalyst and the olefin production

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Paragraph 0147; 0149, (2020/10/31)

PROBLEM TO BE SOLVED: To provide a catalyst for obtaining an olefin in high selectivity with a vicinal diol as a raw material.SOLUTION: A catalyst for olefination reaction for use in a reaction to produce an olefin by a reaction of a polyol, having two adjacent carbon atoms each having a hydroxy group, with hydrogen comprises: a carrier; at least one oxide selected from the group consisting of oxides of the group 6 elements and oxides of the group 7 elements supported on the carrier; and at least one metal selected from the group consisting of silver, iridium, and gold supported on the carrier.SELECTED DRAWING: None

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