تفاعل #446535

ord-890fea3202ca4842b91303d2bd68e315

معادلة التفاعل

C[C@]12CC[C@H](O)CC1=CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
3β-Hydroxyandrost-5-en-17-one
O=O
singlet oxygen
→
C[C@]12CC[C@H]3[C@@H](C=C[C@@]4(OO)C[C@@H](O)CC[C@]34C)[C@@H]1CCC2=O
5α-hydroperoxy-3β-hydroxyandrost-6-en-17-one

المتفاعلات

C[C@]12CC[C@H](O)CC1=CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
3β-Hydroxyandrost-5-en-17-one
O=O
singlet oxygen

الكواشف

لا شيء

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

الإجراء التجريبي

3β-Hydroxyandrost-5-en-17-one (DHEA) 1 reacts with singlet oxygen to yield 5α-hydroperoxy-3β-hydroxyandrost-6-en-17-one 2. This hydroperoxide undergoes a rearrangement when in chloroform solution to yield 7α-hydroperoxy-3β-hydroxyandrost-5-en-17-one, 3. Treatment of the hydroperoxide with zinc and acetic acid yields 3β,7α-dihydroxy-androst-5-en-17-one, 4. ##STR40##

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US05001119uspto-grants-1991_03