Names | |
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IUPAC name (1S,2S,4S)-1,7,7-trimethylbicyclo[2.2.1]heptane-2-ol, (1R,2R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptane-2-ol | |
Identifiers | |
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PubChem CID |
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Properties | |
C10H18O | |
Molar mass | 154.253 g·mol−1 |
Appearance | white or colorless solid |
Melting point | 212–214 °C (414–417 °F; 485–487 K) + or -; 210–215 °C for rac |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Isoborneol is a bicyclic organic compound and a terpene derivative. The hydroxyl group in this compound is placed in an exo position. The endo diastereomer is called borneol. Being chiral, isoborneol exists as enantiomers.
Isoborneol is synthesized commercially by hydrolysis of isobornyl acetate. The latter is obtained from treatment of camphene with acetic acid in the presence of a strong acid catalyst. [1]
It can also be produced by reduction of camphor:
Derivatives of isoborneol are used as ligands in asymmetric synthesis. [2]
In organic chemistry, a ketone is a functional group with the structure R–C(=O)–R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group –C(=O)–. The simplest ketone is acetone, with the formula CH3C(O)CH3. Many ketones are of great importance in biology and in industry. Examples include many sugars (ketoses), many steroids, and the solvent acetone.
Pyrimidine is an aromatic, heterocyclic, organic compound similar to pyridine. One of the three diazines, it has nitrogen atoms at positions 1 and 3 in the ring. The other diazines are pyrazine and pyridazine.
In organic chemistry, an imine is a functional group or organic compound containing a carbon–nitrogen double bond. The nitrogen atom can be attached to a hydrogen or an organic group (R). The carbon atom has two additional single bonds. Imines are common in synthetic and naturally occurring compounds and they participate in many reactions.
Benzoyl chloride, also known as benzenecarbonyl chloride, is an organochlorine compound with the formula C7H5ClO. It is a colourless, fuming liquid with an irritating odour, and consists of a benzene ring with an acyl chloride substituent. It is mainly useful for the production of peroxides but is generally useful in other areas such as in the preparation of dyes, perfumes, pharmaceuticals, and resins.
The Simmons–Smith reaction is an organic cheletropic reaction involving an organozinc carbenoid that reacts with an alkene to form a cyclopropane. It is named after Howard Ensign Simmons, Jr. and Ronald D. Smith. It uses a methylene free radical intermediate that is delivered to both carbons of the alkene simultaneously, therefore the configuration of the double bond is preserved in the product and the reaction is stereospecific.
The chiral pool is a "collection of abundant enantiopure building blocks provided by nature" used in synthesis. In other words, a chiral pool would be a large quantity of common organic enantiomers. Contributors to the chiral pool are amino acids, sugars, and terpenes. Their use improves the efficiency of total synthesis. Not only does the chiral pool contribute a premade carbon skeleton, their chirality is usually preserved in the remainder of the reaction sequence.
Amidines are organic compounds with the functional group RC(NR)NR2, where the R groups can be the same or different. They are the imine derivatives of amides (RC(O)NR2). The simplest amidine is formamidine, HC(=NH)NH2.
In organic chemistry, a sulfonium ion, also known as sulphonium ion or sulfanium ion, is a positively-charged ion featuring three organic substituents attached to sulfur. These organosulfur compounds have the formula [SR3]+. Together with a negatively-charged counterion, they give sulfonium salts. They are typically colorless solids that are soluble in organic solvent.
The Strecker amino acid synthesis, also known simply as the Strecker synthesis, is a method for the synthesis of amino acids by the reaction of an aldehyde with ammonia in the presence of potassium cyanide. The condensation reaction yields an α-aminonitrile, which is subsequently hydrolyzed to give the desired amino acid. The method is used commercially for the production of racemic methionine from methional.
Tetrahydropyran (THP) is the organic compound consisting of a saturated six-membered ring containing five carbon atoms and one oxygen atom. It is named by reference to pyran, which contains two double bonds, and may be produced from it by adding four hydrogens. In 2013, its preferred IUPAC name was established as oxane. The compound is a colourless volatile liquid. Derivatives of tetrahydropyran are, however, more common. 2-Tetrahydropyranyl (THP-) ethers derived from the reaction of alcohols and 3,4-dihydropyran are commonly used as protecting groups in organic synthesis. Furthermore, a tetrahydropyran ring system, i.e., five carbon atoms and an oxygen, is the core of pyranose sugars, such as glucose.
Chiral resolution, or enantiomeric resolution, is a process in stereochemistry for the separation of racemic compounds into their enantiomers. It is an important tool in the production of optically active compounds, including drugs. Another term with the same meaning is optical resolution.
2-Chloropropionic acid (2-chloropropanoic acid) is the chemical compound with the formula CH3CHClCO2H. This colorless liquid is the simplest chiral chlorocarboxylic acid, and it is noteworthy for being readily available as a single enantiomer. The conjugate base of 2-chloropropionic acid (CH3CHClCO2−), as well as its salts and esters, are known as 2-chloropropionates or 2-chloropropanoates.
1,2-Diphenyl-1,2-ethylenediamine, DPEN, is an organic compound with the formula H2NCHPhCHPhNH2, where Ph is phenyl (C6H5). DPEN exists as three stereoisomers: meso and two enantiomers S,S- and R,R-. The chiral diastereomers are used in asymmetric hydrogenation. Both diastereomers are bidentate ligands.
Organoindium chemistry is the chemistry of compounds containing In-C bonds. The main application of organoindium chemistry is in the preparation of semiconducting components for microelectronic applications. The area is also of some interest in organic synthesis. Most organoindium compounds feature the In(III) oxidation state, akin to its lighter congeners Ga(III) and B(III).
Valinol is an organic compound named after, and commonly produced from, the amino acid valine. The compound is chiral and is produced almost exclusively as the S‑isomer, due to the abundant supply of S-valine. It is part of a broader class of amino alcohols.
Ugi’s amine is a chemical compound named for the chemist who first reported its synthesis in 1970, Ivar Ugi. It is a ferrocene derivative. Since its first report, Ugi’s amine has found extensive use as the synthetic precursor to a large number of metal ligands that bear planar chirality. These ligands have since found extensive use in a variety of catalytic reactions. The compound may exist in either the 1S or 1R isomer, both of which have synthetic utility and are commercially available. Most notably, it is the synthetic precursor to the Josiphos class of ligands.
In organophosphorus chemistry, an aminophosphine is a compound with the formula R3−nP(NR2)n where R = H or an organic substituent, and n = 0, 1, 2. At one extreme, the parent H2PNH2 is lightly studied and fragile, but at the other extreme tris(dimethylamino)phosphine (P(NMe2)3) is commonly available. Intermediate members are known, such as Ph2PN(H)Ph. These compounds are typically colorless and reactive toward oxygen. They have pyramidal geometry at phosphorus.
3,5-Dimethylpyrazole is an organic compound with the formula (CH3C)2CHN2H. It is one of several isomeric derivatives of pyrazole that contain two methyl substituents. The compound is unsymmetrical but the corresponding conjugate acid (pyrazolium) and conjugate base (pyrazolide) have C2v symmetry. It is a white solid that dissolves well in polar organic solvents.
N,N-Dimethylaminomethylferrocene is the dimethylaminomethyl derivative of ferrocene, (C5H5)Fe(C5H4CH2N(CH3)2. It is an air-stable, dark-orange syrup that is soluble in common organic solvents. The compound is prepared by the reaction of ferrocene with formaldehyde and dimethylamine:
Alaninol is the organic compound with the formula CH3CH(NH2)CH2OH. A colorless solid, the compound is classified as an amino alcohol. It can be generated by converting the carboxylic group of alanine to an alcohol with a strong reducing agent such as lithium aluminium hydride. The compound is chiral, and as is normal for chiral compounds, the physical properties of the racemate differ somewhat from those of the enantiomers. It is a precursor to numerous chiral ligands used in asymmetric catalysis.