The effect of intramolecular hydrogen bond on reactivity of 6, 7- hydroxyl groups to acetylation in ent-kaurene diterpenoids

Chin. J. Org. Chem. ›› 1996, Vol. 16 ›› Issue (3): 223-226. Previous Articles Next Articles

Original Articles

对映-贝壳杉烯二萜分子内氢键对6, 7位羟基化学反应性影响研究

沈晓羽;吴厚铭;孙汉董

中国科学院上海有机化学研究所生命有机化学;中国科学院植物化学开放实验室

发布日期:1996-06-25

The effect of intramolecular hydrogen bond on reactivity of 6, 7- hydroxyl groups to acetylation in ent-kaurene diterpenoids

SHEN XIAOYU;WU HOUMING;SUN HANDONG

Published:1996-06-25

Abstract

Ent-kaurene diterpenoids were acetylated under a strong reaction condition to afford 7-acetyl products without 6 or 6'-acetyl ones. This uncommon phenomenon may be due to the presence of hydrogen bond (s) between 6-hydroxyl and 15-ketone carbonyl. This hypothesis was unambiguously confirmed by the temperature gradients values △δ/T(Hz.K^-^1) of 6, 6' 7 and 7'-hydroxyl group signal.

Key words: CHEMICAL SHIFT, INTRAMOLECULAR HYDROGEN BOND, DITERPENES, ACETYLATION, KAURENE, ENANTIOMORPH, PROTON MAGNETIC RESONANCE SPECTROMETRY

CLC Number:

O629

Cite this article

SHEN XIAOYU;WU HOUMING;SUN HANDONG. The effect of intramolecular hydrogen bond on reactivity of 6, 7- hydroxyl groups to acetylation in ent-kaurene diterpenoids[J]. Chin. J. Org. Chem., 1996, 16(3): 223-226.

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对映-贝壳杉烯二萜分子内氢键对6, 7位羟基化学反应性影响研究

The effect of intramolecular hydrogen bond on reactivity of 6, 7- hydroxyl groups to acetylation in ent-kaurene diterpenoids

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