Английская Википедия:1,3-Indandione

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Шаблон:Chembox

1,3-Indandione (sometimes simply indanedione) is an organic compound with the molecular formula C6H4(CO)2CH2. It is a β-diketone with indane as its structural nucleus. It is a colorless or white solid, but old samples can appear yellowish[1] or even green. It is a popular chemical scaffold (building block of various useful chemical compounds).[2][3]

Structural properties

Solid 1,3-indandione is a diketone, As a solution in water, it is partially (~2%) enolized. The enolate anion exhibits significant delocalization, and the highest electron density is on the second carbon. This acid-base behavior explains many properties of the compound.Шаблон:Citation needed

Preparation

1,3-Indandione can be prepared by decarboxylation of the sodium salt of 2-ethoxycarbonyl-1,3-indandione, which itself is obtained by Claisen condensation of ethyl acetate and dimethyl phthalate.Шаблон:Citation needed

Файл:Indandione-decarboxilation.svg
Файл:NaECI preparation.svg

Chemical properties

The carbon at the C-2 position is alpha to both carbonyls, and thus can act as a nucleophile. It undergoes self-aldol condensation quite easily, resulting in bindone.

Файл:Bindone-formation.svg

Bromination occurs at the 2-position:

Файл:Bromination 1,3-Indanediol.svg

One or both carbonyl groups can be reduced to alcohol groups or methylene groups, depending on the method used.

Файл:Partial Reduction 1,3-Indanedione.svg
Файл:Reduction 1,3-Indanedione.svg


See also

References

Шаблон:Reflist

External links

Шаблон:Rodenticides Шаблон:Antithrombotics

  1. Шаблон:In lang Нейланд О. Я. Органическая химия: Учеб. для хим. спец. вузов. Москва: Высшая школа, 1990.— с. 481—490.
  2. Шаблон:Cite journal
  3. Шаблон:Cite journal