Propenyl

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In organic chemistry, 1-propenyl (or simply propenyl) has the formula CH=CHCH3 and 2-propenyl (isopropenyl) has the formula CH2=C-CH3. These groups are found in many compounds. Propenyl compounds are isomeric with allyl compounds, which have the formula CH2-CH=CH2.

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The three common precursors to lignin are derivatives of propenylbenzene: paracoumaryl alcohol (1), coniferyl alcohol (2) and sinapyl alcohol (3). Monolignols general.svg
The three common precursors to lignin are derivatives of propenylbenzene: paracoumaryl alcohol (1), coniferyl alcohol (2) and sinapyl alcohol (3).

Chemicals with 1-propenyl groups

Many phenylpropanoids and their derivatives feature derivatives of propenylbenzene:

Chemicals with 2-propenyl groups

p-Isopropenylphenol features a 2-propenyl derivative of phenol. P-isopropenylphenol.svg
p-Isopropenylphenol features a 2-propenyl derivative of phenol.

Several terpenes feature 2-propenyl substituents:

See also

Related Research Articles

In chemistry, a chemical formula is a way of presenting information about the chemical proportions of atoms that constitute a particular chemical compound or molecule, using chemical element symbols, numbers, and sometimes also other symbols, such as parentheses, dashes, brackets, commas and plus (+) and minus (−) signs. These are limited to a single typographic line of symbols, which may include subscripts and superscripts. A chemical formula is not a chemical name since it does not contain any words. Although a chemical formula may imply certain simple chemical structures, it is not the same as a full chemical structural formula. Chemical formulae can fully specify the structure of only the simplest of molecules and chemical substances, and are generally more limited in power than chemical names and structural formulae.

<span class="mw-page-title-main">Ketone</span> Organic compounds of the form >C=O

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 (CH3)2CO. Many ketones are of great importance in biology and in industry. Examples include many sugars (ketoses), many steroids, and the solvent acetone.

<span class="mw-page-title-main">Phenyl group</span> Cyclic chemical group (–C₆H₅)

In organic chemistry, the phenyl group, or phenyl ring, is a cyclic group of atoms with the formula C6H5, and is often represented by the symbol Ph. Phenyl group is closely related to benzene and can be viewed as a benzene ring, minus a hydrogen, which may be replaced by some other element or compound to serve as a functional group. Phenyl group has six carbon atoms bonded together in a hexagonal planar ring, five of which are bonded to individual hydrogen atoms, with the remaining carbon bonded to a substituent. Phenyl groups are commonplace in organic chemistry. Although often depicted with alternating double and single bonds, phenyl group is chemically aromatic and has equal bond lengths between carbon atoms in the ring.

<span class="mw-page-title-main">Acyl group</span> Chemical group (R–C=O)

In chemistry, an acyl group is a moiety derived by the removal of one or more hydroxyl groups from an oxoacid, including inorganic acids. It contains a double-bonded oxygen atom and an organyl group or hydrogen in the case of formyl group. In organic chemistry, the acyl group is usually derived from a carboxylic acid, in which case it has the formula R−C(=O)−, where R represents an organyl group that is linked to the carbon atom of the group by a single bond. Although the term is almost always applied to organic compounds, acyl groups can in principle be derived from other types of acids such as sulfonic acids and phosphonic acids. In the most common arrangement, acyl groups are attached to a larger molecular fragment, in which case the carbon and oxygen atoms are linked by a double bond.

Mesitylene or 1,3,5-trimethylbenzene is a derivative of benzene with three methyl substituents positioned symmetrically around the ring. The other two isomeric trimethylbenzenes are 1,2,4-trimethylbenzene (pseudocumene) and 1,2,3-trimethylbenzene (hemimellitene). All three compounds have the formula C6H3(CH3)3, which is commonly abbreviated C6H3Me3. Mesitylene is a colorless liquid with sweet aromatic odor. It is a component of coal tar, which is its traditional source. It is a precursor to diverse fine chemicals. The mesityl group (Mes) is a substituent with the formula C6H2Me3 and is found in various other compounds.

<span class="mw-page-title-main">Safrole</span> Chemical compound

Safrole is an organic compound with the formula CH2O2C6H3CH2CH=CH2. It is a colorless oily liquid, although impure samples can appear yellow. A member of the phenylpropanoid family of natural products, it is found in sassafras plants, among others. Small amounts are found in a wide variety of plants, where it functions as a natural antifeedant. Ocotea pretiosa, which grows in Brazil, and Sassafras albidum, which grows in eastern North America, are the main natural sources of safrole. It has a characteristic "sweet-shop" aroma.

<span class="mw-page-title-main">Dicarbonyl</span> Molecule containing two adjacent C=O groups

In organic chemistry, a dicarbonyl is a molecule containing two carbonyl groups. Although this term could refer to any organic compound containing two carbonyl groups, it is used more specifically to describe molecules in which both carbonyls are in close enough proximity that their reactivity is changed, such as 1,2-, 1,3-, and 1,4-dicarbonyls. Their properties often differ from those of monocarbonyls, and so they are usually considered functional groups of their own. These compounds can have symmetrical or unsymmetrical substituents on each carbonyl, and may also be functionally symmetrical or unsymmetrical.

<span class="mw-page-title-main">Regioselectivity</span> Preference of chemical bonding or breaking in one direction over others

In chemistry, regioselectivity is the preference of chemical bonding or breaking in one direction over all other possible directions. It can often apply to which of many possible positions a reagent will affect, such as which proton a strong base will abstract from an organic molecule, or where on a substituted benzene ring a further substituent will be added.

<span class="mw-page-title-main">Allyl group</span> Chemical group (–CH₂–CH=CH₂)

In organic chemistry, an allyl group is a substituent with the structural formula −CH2−HC=CH2. It consists of a methylene bridge attached to a vinyl group. The name is derived from the scientific name for garlic, Allium sativum. In 1844, Theodor Wertheim isolated an allyl derivative from garlic oil and named it "Schwefelallyl". The term allyl applies to many compounds related to H2C=CH−CH2, some of which are of practical or of everyday importance, for example, allyl chloride.

<span class="mw-page-title-main">Organotin chemistry</span> Branch of organic chemistry

Organotin chemistry is the scientific study of the synthesis and properties of organotin compounds or stannanes, which are organometallic compounds containing tin carbon bonds. The first organotin compound was diethyltin diiodide, discovered by Edward Frankland in 1849. The area grew rapidly in the 1900s, especially after the discovery of the Grignard reagents, which are useful for producing Sn–C bonds. The area remains rich with many applications in industry and continuing activity in the research laboratory.

Organophosphorus chemistry is the scientific study of the synthesis and properties of organophosphorus compounds, which are organic compounds containing phosphorus. They are used primarily in pest control as an alternative to chlorinated hydrocarbons that persist in the environment. Some organophosphorus compounds are highly effective insecticides, although some are extremely toxic to humans, including sarin and VX nerve agents.

<span class="mw-page-title-main">1,4-Dihydropyridine</span> Chemical compound

1,4-Dihydropyridine (DHP) is an organic compound with the formula CH2(CH=CH)2NH. The parent compound is uncommon, but derivatives of 1,4-dihydropyridine are important commercially and biologically. The pervasive cofactors NADH and NADPH are derivatives of 1,4-dihydropyridine. 1,4-Dihydropyridine-based drugs are L-type calcium channel blockers, used in the treatment of hypertension. 1,2-Dihydropyridines are also known.

<span class="mw-page-title-main">Syringol</span> Chemical compound

Syringol is the organic compound with the formula HO(CH3O)2C6H3. The molecule is a phenol, with methoxy groups in the flanking (2 and 6) positions. It is the symmetrically dimethylated derivative of pyrogallol. It is a colorless solid, although typical samples are brown owing to air-oxidized impurities. Together with guaiacol, syringol and its derivatives are produced by the pyrolysis of lignin. Specifically, syringol is derived from the thermal decomposition of the sinapyl alcohol component. As such, syringol is an important component of wood smoke.

<span class="mw-page-title-main">Copper(I) bromide</span> Chemical compound

Copper(I) bromide is the chemical compound with the formula CuBr. This diamagnetic solid adopts a polymeric structure akin to that for zinc sulfide. The compound is widely used in the synthesis of organic compounds and as a lasing medium in copper bromide lasers.

<span class="mw-page-title-main">Thiosulfinate</span> Functional group

In organosulfur chemistry, thiosulfinate is a functional group consisting of the linkage R-S(O)-S-R. Thiolsulfinates are also named as alkanethiosulfinic acid esters.

<span class="mw-page-title-main">Isoeugenol</span> Chemical compound

Isoeugenol is a phenylpropene, a propenyl-substituted guaiacol. A phenylpropanoid, it occurs in the essential oils of plants such as ylang-ylang, and is a component of wood smoke and liquid smoke. It can be synthesized from eugenol and has been used in the manufacture of vanillin. It may occur as either the cis (Z) or trans (E) isomer. Trans (E) isoeugenol is crystalline while cis (Z) isoeugenol is a liquid. Isoeugenol is one of several phenolic compounds responsible for the mold-inhibiting effect of smoke on meats and cheeses.

<span class="mw-page-title-main">Phenylpropene</span> Chemical compound

Phenylpropene is the organic compound with the formula C6H5CH2CH=CH2. It is a colorless liquid. The compound consists of a phenyl group attached to allyl. Phenylpropene isomerizes to trans-propenylbenzene.

<i>trans</i>-Propenylbenzene Chemical compound

trans-Propenylbenzene is an organic compound with the formula C6H5CH=CHCH3. It is the more stable of the two isomers of 1-propenylbenzene. Both isomers are colorless flammable liquids. It is formed by the isomerization of allylbenzene.

Silanes refers to diverse organosilicon charge-neutral compounds with the formula SiR
4
. The R substituents can any combination of organic or inorganic groups. Most silanes contain Si-C bonds, and are discussed under organosilicon compounds. Some contain Si-H bonds and are discussed under hydrosilanes.

<span class="mw-page-title-main">2-Chloropropylene</span> Chemical compound

2-Chloropropylene is an organochlorine compound with the formula CH2=C(Cl)CH3. It is a colorless gas that condenses just below room temperature. Unlike the closely related vinyl chloride, which is a major industrial chemical, 2-chloropropene has no commercial applications and is a lightly studied compound. In the research laboratory, it is used as a source of the 2-propenyl group. One early synthesis involves dehydrohalogenation of 1,2-dichloropropane with potassium hydroxide.

References

  1. Linstrumelle, Gerard; Krieger, Jeanne K.; Whitesides, George M. (1976). "Preparation of Alkenes by Reaction of Lithium Dipropenylcuprates with Alkyl Halides: (E)-2-Undecene" (PDF). Org. Synth. 55: 103. doi:10.15227/orgsyn.055.0103.