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Names | |||
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Preferred IUPAC name Oxetane [1] | |||
Systematic IUPAC name 1,3-Epoxypropane Oxacyclobutane | |||
Other names 1,3-Propylene oxide Trimethylene oxide | |||
Identifiers | |||
3D model (JSmol) | |||
102382 | |||
ChEBI | |||
ChemSpider | |||
ECHA InfoCard | 100.007.241 | ||
EC Number |
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239520 | |||
PubChem CID | |||
UNII | |||
UN number | 1280 | ||
CompTox Dashboard (EPA) | |||
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Properties | |||
C3H6O | |||
Molar mass | 58.08 g/mol | ||
Density | 0.8930 g/cm3 | ||
Melting point | −97 °C (−143 °F; 176 K) | ||
Boiling point | 49 to 50 °C (120 to 122 °F; 322 to 323 K) | ||
Refractive index (nD) | 1.3895 at 25 °C | ||
Hazards | |||
GHS labelling: | |||
![]() ![]() | |||
Danger | |||
H225, H302, H312, H332 | |||
P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P301+P312, P302+P352, P303+P361+P353, P304+P312, P304+P340, P312, P322, P330, P363, P370+P378, P403+P235, P501 | |||
Flash point | −28.3 °C; −19.0 °F; 244.8 K (NTP, 1992) | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Oxetane, or 1,3-propylene oxide, is a heterocyclic organic compound with the molecular formula C
3H
6O, having a four-membered ring with three carbon atoms and one oxygen atom.
The term "an oxetane" or "oxetanes" refer to any organic compound containing the oxetane ring.
A typical well-known method of preparation is the reaction of potassium hydroxide with 3-chloropropyl acetate at 150 °C: [2]
Yield of oxetane made this way is c. 40%, as the synthesis can lead to a variety of by-products including water, potassium chloride, and potassium acetate.
Another possible reaction to form an oxetane ring is the Paternò–Büchi reaction. The oxetane ring can also be formed through diol cyclization [3] as well as through decarboxylation of a six-membered cyclic carbonate.[ citation needed ]
More than a hundred different oxetanes have been synthesized. [4] Functional groups can be added into any desired position in the oxetane ring, including fully fluorinated (perfluorinated) and fully deuterated analogues. Major examples are:
Name | Structure | Boiling point, Bp [°C] |
---|---|---|
3,3-Bis(chloromethyl)oxetane | ![]() | 198 [5] |
3,3-Bis(azidomethyl)oxetane | ![]() | 165 [6] |
2-Methyloxetane | ![]() | 60 [4] [ failed verification ] |
3-Methyloxetane | ![]() | 67 [4] [ failed verification ] |
3-Azidooxetane | ![]() | 122 [7] |
3-Nitrooxetane | ![]() | 195 [8] |
3,3-Dimethyloxetane | ![]() | 80 [4] [ failed verification ] |
3,3-Dinitrooxetane | ![]() | – |
Paclitaxel (Taxol) is an example of a natural product containing an oxetane ring. Taxol has become a major point of interest among researchers due to its unusual structure and success in the involvement of cancer treatment. [9] The attached oxetane ring is an important feature that is used for the binding of microtubules in structure activity; however little is known about how the reaction is catalyzed in nature, which creates a challenge for scientists trying to synthesize the product. [9]
Oxetane is used in one of the syntheses of Disparlure (Gypsy moth sexual pheromone). [10]
Oxetanes are less reactive than epoxides, and generally unreactive in basic conditions, [11] although Grignard reagents at elevated temperatures [12] and complex hydrides will cleave them. [13] However, the ring strain does make them much more reactive than larger rings, [14] and oxetanes decompose in the presence of even mildly acidic nucleophiles. [15] In non-nucleophilic acids, they mainly isomerize to allyl alcohols. [16]
Noble metals tend to catalyze isomerization to a carbonyl. [17]
In industry, the parent compound, oxetane polymerizes to polyoxetane in the presence of a dry acid catalyst, [18] although the compound was described in 1967 as "rarely polymerized commercially". [19]
In organic chemistry, ethers are a class of compounds that contain an ether group—an oxygen atom connected to two organyl groups. They have the general formula R−O−R′, where R and R′ represent organyl groups. Ethers can again be classified into two varieties: if the organyl groups are the same on both sides of the oxygen atom, then it is a simple or symmetrical ether, whereas if they are different, the ethers are called mixed or unsymmetrical ethers. A typical example of the first group is the solvent and anaesthetic diethyl ether, commonly referred to simply as "ether". Ethers are common in organic chemistry and even more prevalent in biochemistry, as they are common linkages in carbohydrates and lignin.
In chemistry, an ester is a compound derived from an acid in which the hydrogen atom (H) of at least one acidic hydroxyl group of that acid is replaced by an organyl group. Analogues derived from oxygen replaced by other chalcogens belong to the ester category as well. According to some authors, organyl derivatives of acidic hydrogen of other acids are esters as well, but not according to the IUPAC.
Phthalic anhydride is the organic compound with the formula C6H4(CO)2O. It is the anhydride of phthalic acid. Phthalic anhydride is a principal commercial form of phthalic acid. It was the first anhydride of a dicarboxylic acid to be used commercially. This white solid is an important industrial chemical, especially for the large-scale production of plasticizers for plastics. In 2000, the worldwide production volume was estimated to be about 3 million tonnes per year.
In organic chemistry, thioesters are organosulfur compounds with the molecular structure R−C(=O)−S−R’. They are analogous to carboxylate esters with the sulfur in the thioester replacing oxygen in the carboxylate ester, as implied by the thio- prefix. They are the product of esterification of a carboxylic acid with a thiol. In biochemistry, the best-known thioesters are derivatives of coenzyme A, e.g., acetyl-CoA. The R and R' represent organyl groups, or H in the case of R.
The Friedel–Crafts reactions are a set of reactions developed by Charles Friedel and James Crafts in 1877 to attach substituents to an aromatic ring. Friedel–Crafts reactions are of two main types: alkylation reactions and acylation reactions. Both proceed by electrophilic aromatic substitution.
In organometallic chemistry, organolithium reagents are chemical compounds that contain carbon–lithium (C–Li) bonds. These reagents are important in organic synthesis, and are frequently used to transfer the organic group or the lithium atom to the substrates in synthetic steps, through nucleophilic addition or simple deprotonation. Organolithium reagents are used in industry as an initiator for anionic polymerization, which leads to the production of various elastomers. They have also been applied in asymmetric synthesis in the pharmaceutical industry. Due to the large difference in electronegativity between the carbon atom and the lithium atom, the C−Li bond is highly ionic. Owing to the polar nature of the C−Li bond, organolithium reagents are good nucleophiles and strong bases. For laboratory organic synthesis, many organolithium reagents are commercially available in solution form. These reagents are highly reactive, and are sometimes pyrophoric.
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.
In organic chemistry, nitro compounds are organic compounds that contain one or more nitro functional groups. The nitro group is one of the most common explosophores used globally. The nitro group is also strongly electron-withdrawing. Because of this property, C−H bonds alpha (adjacent) to the nitro group can be acidic. For similar reasons, the presence of nitro groups in aromatic compounds retards electrophilic aromatic substitution but facilitates nucleophilic aromatic substitution. Nitro groups are rarely found in nature. They are almost invariably produced by nitration reactions starting with nitric acid.
A trimethylsilyl group (abbreviated TMS) is a functional group in organic chemistry. This group consists of three methyl groups bonded to a silicon atom [−Si(CH3)3], which is in turn bonded to the rest of a molecule. This structural group is characterized by chemical inertness and a large molecular volume, which makes it useful in a number of applications.
Palladium(II) acetate is a chemical compound of palladium described by the formula [Pd(O2CCH3)2]n, abbreviated [Pd(OAc)2]n. It is more reactive than the analogous platinum compound. Depending on the value of n, the compound is soluble in many organic solvents and is commonly used as a catalyst for organic reactions.
The Nicolaou Taxol total synthesis, published by K. C. Nicolaou and his group in 1994 concerns the total synthesis of taxol. Taxol is an important drug in the treatment of cancer but also expensive because the compound is harvested from a scarce resource, namely the pacific yew.
Ring-closing metathesis (RCM) is a widely used variation of olefin metathesis in organic chemistry for the synthesis of various unsaturated rings via the intramolecular metathesis of two terminal alkenes, which forms the cycloalkene as the E- or Z- isomers and volatile ethylene.
The Peterson olefination is the chemical reaction of α-silyl carbanions with ketones to form a β-hydroxysilane (2) which eliminates to form alkenes (3).
The Danishefsky Taxol total synthesis in organic chemistry is an important third Taxol synthesis published by the group of Samuel Danishefsky in 1996 two years after the first two efforts described in the Holton Taxol total synthesis and the Nicolaou Taxol total synthesis. Combined they provide a good insight in the application of organic chemistry in total synthesis.
Wender Taxol total synthesis in organic chemistry describes a Taxol total synthesis by the group of Paul Wender at Stanford University published in 1997. This synthesis has much in common with the Holton Taxol total synthesis in that it is a linear synthesis starting from a naturally occurring compound with ring construction in the order A,B,C,D. The Wender effort is shorter by approximately 10 steps.
The Varrentrapp reaction, also named Varrentrapp degradation, is a name reaction in the organic chemistry. It is named after Franz Varrentrapp, who described this reaction in 1840. The reaction entails the degradation of an unsaturated carboxylic acid into a saturated acid with two fewer carbon atoms and acetic acid. The fragmentation is induced by action of molten alkali.
The Mukaiyama taxol total synthesis published by the group of Teruaki Mukaiyama of the Tokyo University of Science between 1997 and 1999 was the 6th successful taxol total synthesis. The total synthesis of Taxol is considered a hallmark in organic synthesis.
The Takahashi Taxol total synthesis published by Takashi Takahashi in 2006 is one of several methods in taxol total synthesis. The method starts from geraniol and differs from the other 6 published methods that it is a formal synthesis and that it is racemic. A key feature of the published procedure is that several synthetic steps were performed in an automated synthesizer on a scale up to 300 gram and that purification steps were also automated.
2,2,4,4-Tetramethylcyclobutanedione is the organic compound with the formula (CH3)4C4O2. The compound is a diketone of cyclobutane, bearing four methyl groups. It is a white solid that is used as a precursor to diverse industrial products.
Polyoxetane (POX), or poly(oxetane), is synthetic organic heteroatomic thermoplastic polymer with molecular formula (–OCH2CH2CH2–)n. It is polymerized from oxetane monomer, which is a four-membered cyclic ether.
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