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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/12/23 09:28:19」(JST)
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| Pyrrolidine |
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Other names
azolidine, azacyclopentane, tetrahydropyrrole
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| Identifiers |
| CAS number |
123-75-1 Y |
| PubChem |
31268 |
| ChemSpider |
29008 Y |
| UNII |
LJU5627FYV Y |
| ChEBI |
CHEBI:33135 Y |
| ChEMBL |
CHEMBL22830 Y |
| RTECS number |
UX9650000 |
| Jmol-3D images |
Image 1 |
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InChI=1S/C4H9N/c1-2-4-5-3-1/h5H,1-4H2 Y
Key: RWRDLPDLKQPQOW-UHFFFAOYSA-N Y
InChI=1/C4H9N/c1-2-4-5-3-1/h5H,1-4H2
Key: RWRDLPDLKQPQOW-UHFFFAOYAX
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| Properties |
| Molecular formula |
C4H9N |
| Molar mass |
71.12 g mol−1 |
| Appearance |
Clear colorless liquid |
| Density |
0.866 g/cm3 |
| Melting point |
−63 °C; −81 °F; 210 K |
| Boiling point |
87 °C; 189 °F; 360 K |
| Solubility in water |
Miscible |
| Acidity (pKa) |
11.27 (pKa of conjugate acid in water),[1]
19.56 (pKa of conjugate acid in acetonitrile)[2]
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| Hazards |
| MSDS |
MSDS |
| R-phrases |
R11-R20/21/22-R34[3] |
| S-phrases |
S16-S26-S28-S36/37-S45 |
| Main hazards |
highly flammable, harmful, corrosive, possible mutagen |
| NFPA 704 |
|
| Flash point |
3 °C; 37 °F; 276 K |
| Autoignition temperature |
345 °C; 653 °F; 618 K |
| Related compounds |
| Related Nitrogen heterocyclic compounds |
Pyrrole (aromatic with two double bonds)
Pyrroline (one double bond)
Pyrrolizidine (two pentagonal rings) |
Y (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa) |
| Infobox references |
Pyrrolidine, also known as tetrahydropyrrole, is an organic compound with the molecular formula (CH2)4NH. It is a cyclic secondary amine, also classified as a saturated heterocycle. It is a colourless liquid that is miscible with water and most organic solvents. It has a characteristic odor that is ammoniacal, fishy, shellfish-like.[4] Compared to acyclic secondary amines, it is about 10 times more basic.
Synthesis and occurrence[edit]
Pyrrolidine is produced industrially by treatment of 1,4-butanediol with ammonia over an oxide catalyst.[5]
Pyrrolidine is found in the leaves of tobacco and carrot. The pyrrolidine ring structure is present in numerous natural alkaloids such as nicotine and hygrine. It is found in many pharmaceutical drugs such as procyclidine and bepridil. It also forms the basis for the racetam compounds (e.g. piracetam, aniracetam). The amino acids proline and hydroxyproline are, in a structural sense, derivatives of pyrrolidine.
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Nicotine contains an
N-methylpyrrolidine ring linked to a pyridine ring.
Applications[edit]
Pyrrolidine is used as a building block in the synthesis of more complex compounds. In organic chemistry, pyrrolidine is used to activate ketones and aldehydes toward nucleophilic addition by formation of enamines:[6]
References[edit]
- ^ Hall, H. K. (1957). "Correlation of the Base Strengths of Amines". Journal of the American Chemical Society 79 (20): 5441. doi:10.1021/ja01577a030. edit
- ^ Kaljurand, I.; Kütt, A.; Sooväli, L.; Rodima, T.; Mäemets, V.; Leito, I.; Koppel, I. A. (2005). "Extension of the Self-Consistent Spectrophotometric Basicity Scale in Acetonitrile to a Full Span of 28 pKa Units: Unification of Different Basicity Scales". The Journal of Organic Chemistry 70 (3): 1019–1028. doi:10.1021/jo048252w. PMID 15675863. edit
- ^ MSDS
- ^ Pyrrolidine, The Good Scents Company
- ^ Karsten Eller, Erhard Henkes, Roland Rossbacher, Hartmut Höke "Amines, Aliphatic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005. doi:10.1002/14356007.a02_001
- ^ R. B. Woodward, I. J. Pachter, and M. L. Scheinbaum (1974), "2,2-(Trimethylenedithio)cyclohexanone", Org. Synth. 54: 39 ; Coll. Vol. 6: 1014
UpToDate Contents
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English Journal
- Chiral/ring closed vs. achiral/open chain triazine-based organogelators: induction and amplification of supramolecular chirality in organic gels.
- Lascialfari L1, Berti D, Brandi A, Cicchi S, Mannini M, Pescitelli G, Procacci P.
- Soft matter.Soft Matter.2014 Jun 7;10(21):3762-70. doi: 10.1039/c4sm00354c. Epub 2014 Apr 15.
- The purpose of this study is to compare the gelling behavior of two molecules: a chiral compound and its achiral counterpart. The chiral partner is characterized by a rigid, chiral pyrrolidine nucleus, while the achiral one contains a flexible diethanolamine moiety. The chiral compound is an already
- PMID 24733431
- A chiral benzoylthiourea-pyrrolidine catalyst for the highly enantioselective Michael addition of ketones to chalcones.
- Ban SR1, Zhu XX2, Zhang ZP2, Li QS3.
- Bioorganic & medicinal chemistry letters.Bioorg Med Chem Lett.2014 Apr 13. pii: S0960-894X(14)00341-2. doi: 10.1016/j.bmcl.2014.04.005. [Epub ahead of print]
- A benzoylthiourea-pyrrolidine catalyst was developed for the asymmetric Michael addition of ketones to chalcones. The corresponding products were obtained in high yields with high level of diastereoselectivities (up to 99:1 dr) and high level of enantioselectivities (up to 94% ee) under mild conditi
- PMID 24755429
- Testing for Designer Stimulants: Metabolic Profiles of 16 Synthetic Cathinones Excreted Free in Human Urine.
- Uralets V1, Rana S, Morgan S, Ross W.
- Journal of analytical toxicology.J Anal Toxicol.2014 Mar 25. [Epub ahead of print]
- The study of 34,561 urine specimens, submitted for designer stimulant testing between February 2011 and January 2013, provided an opportunity: to estimate the range of synthetic cathinones (SC) abused in the USA, to observe multiple examples of metabolic profiles for each drug in various stages of e
- PMID 24668489
Japanese Journal
- Antitumor effect of sonodynamically activated pyrrolidine tris-acid fullerene
- Catalytic discrimination between formyl groups in regio-and stereoselective intramolecular cross-Aldol reactions
- Practical Total Syntheses of Acromelic Acids A and B
Related Links
- [Pyrrolidine] [123-75-1] | 価格や在庫、物性値などの詳細情報ページです。 ... ・川口の在庫は即日，つくばの在庫は2〜3日以内の出荷となります。・詳細につきましては，お手数ですが営業部までお問い合わせください。
- Sigma-Aldrich offers Aldrich-394238, Pyrrolidine for your research needs. Find product specific information including CAS, MSDS, protocols and references. ... Packaging 1 L in Sure/Seal 100 mL in Sure/Seal
Related Pictures
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- 英
- pyrrolidine
- (アザシクロペンタン)pyrrolidine、(アザペンタレン)pyrrolizine
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- pyrrolidine
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