2,2':5',2"-ターチオフェン 化学特性,用途語,生産方法
外観
わずかにうすい黄色～黄色、結晶～結晶性粉末
用途
有機合成原料。
化学的特性
YELLOW TO YELLOW-BROWN POWDER
使用
α-Terthienyl was first recognized as a nematicidal
constituent of marigolds, but in the presence of light, it
is also highly toxic to larvae of several insect species,
including mosquitoes. This electron donor thiophenederivative
phototoxin is biosynthesized from polyacetylene
precursors and appears to function as a photosensitizer
catalyzing the formation of reactive oxygen species at the
target site (25).
一般的な説明
2,2′:5′,2′′-Terthiophene (TTh) may be prepared by nickel catalysed coupling reaction of grignard′s reagent derived from 2-bromothiophene and magnesium. It generates singlet oxygen. In nature, it is found in the floral extract of
Tagetes minuta and
Echinops grijisii. It is known to be toxic to mosquitoes. It also exihibits antifungal activity.
合成
A common method for synthesizing 2,2':5',2''-terthiophene is a metal-catalyzed coupling reaction. This reaction can be obtained by coupling a Grignard reagent prepared with 2,5-dibromothiophene and 2-bromothiophene under nickel or palladium catalysis.
代謝経路
When 14C-a-terthienyl is administered orally to rats in
a single dose, two metabolites [1,4-di(2'-thienyl)]-1,4-
butadione and 2-2' -bithiophene-5-carboxylic acid are
identified in the urine.
純化方法
Possible impurities are bithienyl and polythienyls. Suspend it in H2O and steam distil it to remove bithienyl. The residue is cooled and extracted with CHCl3, dried (MgSO4), filtered, evaporated and the residue chromatographed on Al2O3 using pet ether/3% Me2CO as eluent. The terphenyl zone is then eluted from the Al2O3 with Et2O, the extract is evaporated and the residue is recrystallised from MeOH (40mL per g). The platelets are washed with cold MeOH and dried in air. [UV: Sease & Zechmeister J Am Chem Soc 69 270 1947; Uhlenbroek & Bijloo Recl Trav Chim Pays-Bas 79 1181 1960.] It has also been recrystallised from MeOH, *C6H6, pet ether or AcOH. [UV: Zechmeister & Sease J Am Chem Soc 69 273 1947, Steinkopf et al. Justus Liebigs Ann Chem 546 180 1941.] It is a phototoxic nematocide [Cooper & Nitsche Bioorg Chem 13 36 1985, Chan et al. Phytochem 14 2295 1975]. [Beilstein 19 III/IV 4763, 19/9 V 226.]
2,2':5',2"-ターチオフェン 上流と下流の製品情報
原材料
準備製品