“Pyridazine”的意思、由来-开放百科全书

词条

Pyridazine

释义

Occurrence
Synthesis
References

{{Chembox
| Watchedfields = changed
| verifiedrevid = 464376879
| ImageFile = Pyridazine 2D numbers.svg
| ImageSize = 135
| ImageAlt = Skeletal formula with numbering convention
| ImageFileL1_Ref = {{chemboximage|correct|??}}
| ImageFileL1=Pyridazine-3D-balls.png
| ImageNameL1 = C=black, H=white, N=blue
| ImageAltL1 = Pyridazine molecule
| ImageFileR1=Pyridazine-3D-spacefill.png
| ImageNameR1 = C=black, H=white, N=blue
| ImageAltR1 = Pyridazine molecule
| PIN = Pyridazine
| OtherNames = 1,2-Diazine
Orthodiazine
Oizine
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 8902
| InChI = 1/C4H4N2/c1-2-4-6-5-3-1/h1-4H
| InChIKey = PBMFSQRYOILNGV-UHFFFAOYAA
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 15719
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C4H4N2/c1-2-4-6-5-3-1/h1-4H
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = PBMFSQRYOILNGV-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo=289-80-5
| PubChem = 9259
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 30954
| SMILES = c1ccnnc1
| RTECS=GY2390000
| EINECS = 206-025-5
|Section2={{Chembox Properties
| Formula= | C=4 | H=4 | N=2
| MolarMass=80.09 g/mol
| Appearance=colorless liquid
| Density=1.107 g/cm³
| MeltingPtC=-8
| BoilingPtC=208
| Solubility= miscible
| SolubleOther = miscible in dioxane, ethanol
soluble in benzene, diethyl ether
negligible in cyclohexane, ligroin
| pKa =
| pKb =
| RefractIndex = 1.52311 (23.5 °C)
|Section3={{Chembox Thermochemistry
| DeltaHf = 224.9 kJ/mol
|Section7={{Chembox Hazards
| MainHazards=
| FlashPtC= 85
| AutoignitionPt =
|Section8={{Chembox Related
| OtherCompounds = pyridine, pyrimidine, pyrazine
}}

Pyridazine is a heterocyclic organic compound with the molecular formula (CH)₄N₂. It contains a six-membered ring with two adjacent nitrogen atoms, and is aromatic.^[1] It is a colorless liquid with a boiling point of 208 °C. It is isomeric with two other (CH)₄N₂ rings, pyrimidine and pyrazine.

Occurrence

Pyridazines are rare in nature, possibly reflecting the scarcity of naturally occurring hydrazines, common building blocks for the synthesis of these heterocycles. The pyridazine structure is a popular pharmacophore which is found within a number of herbicides such as credazine, pyridafol and pyridate. It is also found within the structure of several drugs such as cefozopran, cadralazine, minaprine, pipofezine, and hydralazine.

Synthesis

In the course of his classic investigation on the Fischer indole synthesis, Emil Fischer prepared the first pyridazine via the condensation of phenylhydrazine and levulinic acid.^[2] The parent heterocycle was first prepared by oxidation of benzocinnoline to the pyridazinetetracarboxylic acid followed by decarboxylation. A better route to this otherwise esoteric compound starts with the maleic hydrazide. These heterocycles are often prepared via condensation of 1,4-diketones or 4-ketoacids with hydrazines.^[3]

References

1. ^{{cite journal | last1 = Gumus | first1 = S. | year = 2011 | title = A computational study on substituted diazabenzenes | url = http://journals.tubitak.gov.tr/chem/issues/kim-11-35-5/kim-35-5-11-1012-875.pdf | format = PDF | journal = Turk J Chem | volume = 35 | issue = | pages = 803–808 }}
2. ^{{cite journal | last1 = Fischer | first1 = E. | year = 1886 | title = Indole aus Phenylhydrazin | url = | journal = Justus Liebigs Annalen der Chemie | volume = 236 | issue = 1-2| pages = 126–151 | doi = 10.1002/jlac.18862360107 }}
3. ^{{cite journal | last1 = Tišler | first1 = M. | last2 = Stanovnik | first2 = B. | year = 1968 | title = Pyridazines | url = | journal = Advances in Heterocyclic Chemistry | volume = 9 | issue = | pages = 211–320 | doi = 10.1016/S0065-2725(08)60374-8 }}

2 : Pyridazines|Simple aromatic rings

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