HRID2397523

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID6775

2,3-Dichloro-5,6-dicyano-p-benzoquinone

C8Cl2N2O2

结构：C[C@H](CCCC(C)(C)O)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C

HCID65094

25-Hydroxycholesterol

C27H46O2

PRODUCTS

生成物

结构：C[C@H](CCCC(C)(C)O)[C@H]1CC[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@H]3CC[C@]12C

HCID54187257

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID31275

1,4-Dioxane

C4H8O2

PROCEDURE

实验过程

The 25-hydroxycholesterol was dissolved in dioxane and boiled with 2,3-dichloro-5,6-dicyanobenzo-quinone (DDQ) to obtain 25-hydroxycholesta-1,4-diene-3-one. This latter compound was subjected to dehydrogenation with chloroanil in the presence of the reduced derivative of DDQ-hydroquinone (2HDDQ) to obtain 25-hydroxy-cholesta-1,4,6-triene-3-one. Alternatively, 25-hydroxy-cholesta-1,4,6-trien-3-one can be obtained by DDQ oxidation of 25-hydroxycholesterol (J. J. Partridge et al., Helv. Chim. Acta 57, 764 (1974) which was converted from 6β-methoxy-25-hydroxy-3α,5-cyclo-5α-cholestane.