71749-03-6

Basic information

• Product Name: (+)-TRANS-1,2-CYCLOHEXANEDICARBOXYLIC ANHYDRIDE
• Synonyms: (+)-TRANS-1,2-CYCLOHEXANEDICARBOXYLIC ANHYDRIDE;Cyclohexanedicarboxylicanhydride;(R,R)-1,2-Cyclohexanedicarboxylic anhydride;(3aR,7aR)-hexahydro-2-benzofuran-1,3-dione;(3aR,7aR)-hexahydro-1,3-Isobenzofurandione;(+)-trans-1,2-Cyclohexanedicarboxylic Anhydride
• CAS NO: 71749-03-6
• Molecular Formula: C₈H₁₀O₃
• Molecular Weight: 154.16
• Product Categories: chiral;for Resolution of Alcohols & Thiols;for Resolution of Bases;Optical Resolution;Synthetic Organic Chemistry
• Mol File: 71749-03-6.mol

Chemical Properties

• Melting Point: 165 °C
• Boiling Point: 283.4±0.0 °C(Predicted)
• Appearance: /
• Density: 1.235±0.06 g/cm3(Predicted)
• Refractive Index: 85 ° (C=1, Dioxane)
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: soluble in Dioxane
• CAS DataBase Reference: (+)-TRANS-1,2-CYCLOHEXANEDICARBOXYLIC ANHYDRIDE(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-TRANS-1,2-CYCLOHEXANEDICARBOXYLIC ANHYDRIDE(71749-03-6)
• EPA Substance Registry System: (+)-TRANS-1,2-CYCLOHEXANEDICARBOXYLIC ANHYDRIDE(71749-03-6)

Safety Data

• Hazard Codes: Xn
• Statements: 41-42/43
• Safety Statements: 23-24-26-37/39
• Hazardous Substances Data: 71749-03-6(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
(+)-trans-1,2-Cyclohexanedicarboxylic anhydride is used as a reagent in chemical synthesis for its ability to participate in esterification, acylation, and the formation of acid halides. Its cyclic structure and anhydride properties make it a valuable component in creating a variety of complex organic molecules.
Used in Research Applications:
In the field of research, (+)-trans-1,2-Cyclohexanedicarboxylic anhydride serves as a key compound for studying the reactions and mechanisms involving anhydrides. Its unique structure allows scientists to explore new pathways and develop innovative synthetic methods.
Used in Pharmaceutical Industry:
(+)-trans-1,2-Cyclohexanedicarboxylic anhydride is used as an intermediate in the synthesis of pharmaceutical compounds. Its reactivity and structural features contribute to the development of new drugs and active pharmaceutical ingredients.
Used in Material Science:
In material science, (+)-trans-1,2-Cyclohexanedicarboxylic anhydride is utilized in the synthesis of polymers and other materials with specific properties. Its ability to undergo various chemical reactions enables the creation of materials with tailored characteristics for different applications.
Used in Agrochemical Industry:
(+)-trans-1,2-Cyclohexanedicarboxylic anhydride is employed as a building block in the production of agrochemicals, such as pesticides and herbicides. Its role in the synthesis of these compounds contributes to the development of effective and targeted agricultural products.
Used in Flavor and Fragrance Industry:
(+)-trans-1,2-Cyclohexanedicarboxylic anhydride is used as a precursor in the synthesis of various flavor and fragrance compounds. Its versatility in chemical reactions allows for the creation of unique and complex scents and tastes.

Upstream product

• 46022-05-3 (1R,2R)-(-)-trans-cyclohexane-1,2-dicarboxylic acid 
• 610-10-6 (1S,2S)-cyclohexane-1,2-dicarboxylic acid 

Downstream Products

• 147201-75-0 (1R,2R)-2-[(Benzyloxycarbamoyl-methyl)-methyl-carbamoyl]-cyclohexanecarboxylic acid 
• 288314-19-2 (1R,2R)-cyclohexane-1,2-dicarboxylic acid mono-n-propylamide 
• 488703-59-9 (1R)-trans-2-carbamoyl-cyclohexanecarboxylic acid 
• 288314-21-6 (1R,2R)-2-Propylcarbamoyl-cyclohexanecarbonyl fluoride 
• 288314-03-4 (3S,4S)-3,4-Bis-[((1R,2R)-2-{2-[4-(2-{ethyl-[4-(4-nitro-phenylazo)-phenyl]-amino}-ethoxy)-phenyl]-ethylcarbamoyl}-cyclohexanecarbonyl)-amino]-pyrrolidine-1-carboxylic acid 2-trimethylsilanyl-ethyl ester 
• 174592-16-6 (trans)-1,2-cyclohexanedicarboxylic acid, mono(phenylmethyl)ester 
• 488703-61-3 (1S)-trans-2-carbamoyl-cyclohexanecarboxylic acid 
• 1095263-14-1 (1R,2R)-N-(1-cyanocyclopropyl)-2-[(8-fluoro-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indol-2-yl)carbonyl]cyclohexanecarboxamide 
• 1095263-56-1 (1R,2R)-N-(1-cyanocyclopropyl)-2-(6-(2-(dimethylamino)ethoxy)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole-2-carbonyl)cyclohexanecarboxamide 
• 1095534-50-1 (1R,2R)-N-(1-cyanocyclopropyl)-2-{[4-(3-methylpyridin-2-yl)piperazin-1-yl]carbonyl}cyclohexanecarboxamide 

Relevant articles and documents

Synthesis method of trans 1 and 2 - cyclohexane dicarboxylic acid monomethylester

The invention provides a synthesis method of trans 1 and 2 - cyclohexane dicarboxylic acid monomethylester, and belongs to the field of organic synthesis. The trans 1-2 -cyclohexane dicarboxylic acid monomethylester synthesis method comprises the following steps: trans-cyclohexane -1 and 2 -dicarboxylic acid anhydride. The methanol and solvent is added to the reaction vessel, stirred and purified to obtain the target product trans 1, 2 - cyclohexanedicarboxylate, wherein the solvent is any one or more of tetrahydrofuran, 2 - methyltetrahydrofuran, benzene, toluene, methylene chloride, chloroform, ethyl acetate, methyl acetate or diethyl ether. Since a specific solvent is selected for the reaction solvent, racemization does not occur in the process of synthesizing trans 1 and 2 - cyclohexane dicarboxylic acid monomethyl ester, and the trans ee and 1 cyclohexane dicarboxylic acid monomethyl ester with higher 2 - value can be finally obtained.

RECYCLABLE POLYMERS BASED ON RING-FUSED GAMMA-BUTYROLACTONES

The invention discloses a class of new polymers, trans-ring-fused poly(4-hydroxybutyrate)s (RF-P4HB) that exhibit a unique set of properties, including robust thermal stability and mechanical strength, quantitative recyclability to the building block monomers via thermolysis and/or chemical catalysis, and convenient production from the chemical ring-opening polymerization under ambient temperature and pressure. Another unique property is the formation of crystalline stereocomplexed polymers with high melting temperature upon mixing the two enantiomeric RF-P4HB chains via stereocomplexing co-crystallization. This invention also provides the corresponding ring-fused lactone monomer structures that enable the synthesis of the RF-P4HB polymers, through trans-fusing of rings to the parent γ-butyrolactone ring. Furthermore, a polymerization or copolymerization process for the synthesis of RF-P4HB polymers and copolymers is disclosed.

Exploring the active conformation of cyclohexane carboxylate positive allosteric modulators of the type 4 metabotropic glutamate receptor

The active conformation of a family of metabotropic glutamate receptor subtype 4 (mGlu4) positive allosteric modulators (PAMs) with the cyclohexane 1,2-dicarboxylic scaffold present in cis-2-(3,5-dichlorophenylcarbamoyl)cyclohexanecarboxylic acid (VU0155041) was investigated by testing structurally similar six-membered ring compounds that have a locked conformation. The norbornane and cyclohexane molecules designed as mGlu4 conformational probes and the enantiomers of the trans diastereomer were computationally characterized and tested in mGlu4 pharmacological assays. The results support a VU0155041 active conformation, with the chair cyclohexane having the aromatic amide substituent in an axial position and the carboxylate in an equatorial position. Moreover, the receptor displays enantiomeric discrimination of the chiral PAMs. The constructed pharmacophore characterized a highly constrained mGlu4 allosteric binding site, thus providing a step forward in structure-based drug design for mGlu4 PAMs.

NOVEL HEPATITIS C VIRUS INHIBITORS

The invention provides compounds of formula (I): wherein Rings A and A' are independently 5-membered optionally substituted aromatic heterocycles; Q is C(=O)NR1R1' or formula U is C(R4)2, O, S, S(=O)2, C(R4)2C(R4)2, CH2O, OCH2, CH2S, SCH2, CH2S(=O)2, S(=O)CH2 or C=C(Ru )2; X is CH2, CHR12, CR12R12, O, S, S(=O)2 or NRx; m is 0, 1, 2 or 3; n is 0, 1, 2 or 3; the other variables are as defined in the claims, which are of use in the treatment or prophylaxis of hepatitis C virus infection, and related aspects.

(1 R,2 R)-N-(1-cyanocyclopropyl)-2-(6-methoxy-1,3,4,5-tetrahydropyrido[4,3- b]indole-2-carbonyl)cyclohexanecarboxamide (AZD4996): A potent and highly selective cathepsin k inhibitor for the treatment of osteoarthritis

Directed screening of nitrile compounds revealed 3 as a highly potent cathepsin K inhibitor but with cathepsin S activity and very poor stability to microsomes. Synthesis of compounds with reduced molecular complexity, such as 7, revealed key SAR and demonstrated that baseline physical properties and in vitro stability were in fact excellent for this series. The tricycle carboline P3 unit was discovered by hypothesis-based design using existing structural information. Optimization using small substituents, knowledge from matched molecular pairs, and control of lipophilicity yielded compounds very close to the desired profile, of which 34 (AZD4996) was selected on the basis of pharmacokinetic profile.

Novel Compound - 827

The present invention relates to compounds and compositions for treating diseases associated with cysteine protease activity. The compounds are reversible inhibitors of cysteine proteases, including cathepsins B, K, C, F, H, L, O, S, W and X. Of particular interest are diseases associated with Cathepsin K.

1,2-CYCL0HEXANE DICARBOXAMIDES AS CATHEPSIN INHIBITORS

The present invention relates to compounds and compositions for treating diseases associated with cysteine protease activity. The compounds are reversible inhibitors of cysteine proteases, including cathepsins B, K, C, F, H, L, O, S, W and X. Of particular interest are diseases associated with Cathepsin K.

Enantiomerically pure β-amino acids: A convenient access to both enantiomers of trans-2-aminocyclohexanecarboxylic acid

Enantiomerically pure trans-2-aminocyclohexanecarboxylic acid is an important building block for helical β-peptides. We report here that this amino acid can be obtained from trans-cyclohexane-1,2-dicarboxylic acid in good yield by a simple one-pot procedure comprising cyclization to the anhydride, amide formation with ammonia, and a subsequent Hofmann-type degradation with phenyliodine(III) bis(trifluoroacetate) (PIFA) as the oxidant. The N-Fmoc- and N-BOC-protected derivatives were obtained by treatment of the amino acid with Fmoc-OSu and BOC2O, respectively. The N-BOC derivative could be prepared in even better overall yield by a one-pot procedure leading directly from trans-cyclohexane-1,2-dicarboxylic acid to the N-BOC-protected amino acid. Both enantiomers of the starting trans-1,2-cyclohexanedicarboxylic acid can be obtained easily and in large quantities by separating commercially available racemic trans-1,2-cyclohexanedicarboxylic acid using either (R)- or (S)-1-phenethylamine. X-ray crystallography of the diastereomerically pure salt obtained from (R)-1-phenethylamine revealed that the configuration of the diacid component is (1R,2R), and not (1S,2S) as reported in the literature. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

DRUG DISCHARGE PUMP INHIBITORS

A medicament for preventive and/or therapeutic treatment of a microbial infection having an activity of eliminating resistance of a microorganism with acquired resistance to an antimicrobial agent, which comprises as an active ingredient a compound represented by the following general formula (I), a physiologically acceptable salt thereof, or a hydrate thereof: wherein R1 and R2 independently represent hydrogen atom, a halogen atom, carboxyl group and the like; J1 represents a 5- or 6-membered heteroaromatic ring; W1 represents -CH=CH-, -C≡C-, -CH2CH2- and the like; A1 represents phenylene group, pyridinediyl group, furandiyl group and the like; G1 represents oxygen atom, carbonyl group, ethynyl group and the like; p represents an integer of from 0 to 3; G2 represents phenylene group, furandiyl group, tetrahydrofurandiyl group and the like; G3 represents -CH2- or single bond; m and n represent an integer of 0 or 1; and Q1 represents an acidic group.