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化学学报
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化学学报 ›› 1956, Vol. 22 ›› Issue (6): 493-506. 上一篇    下一篇

论文

山道年一类物之研究——Ⅵ.变质山道年的相对构型

黄鸣龙, 周维善   

  1. 医学科学院化学系
  • 投稿日期:1956-08-02 发布日期:2013-06-03

STUDIES ON THE SANTONIN SERIES Ⅵ.[1] THE RELATIVE CONFIGURATION OF DESMOTROPOSANTONINS

HUANG MINLONG(HUANG-MINLON), CHOW WEI-ZAN   

  1. Department of Chemistry, Institute of Medical Sciences
  • Received:1956-08-02 Published:2013-06-03

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813

被引次数

2

1.四种变质山道年(A,B,C,D)经乙醇性盐酸处理,即可除去C5C6的旋光中枢,而祇留C11的旋光中枢,所得的镜体(Ⅳ和Ⅴ)可以证明变质山道年在龄时旋光度增减特异之处,确系邻位影响所致(参看493页,B→C及D→A),并且可以进一步在实验上证明变质山道年的酸变机构。2.用接触氢化不饱和酯体(Ⅳ及Ⅴ)的结果,可以证明此物的变键位置及其分子的结构,并且证明变质山道年在强酸条件下变成Ⅳ及Ⅴ时,并未变动C11的构型。3.两种系统的变质山道年(A,C及B,D)对乙醇性盐酸的感应性不同,α-系统变质山道年的内酯环对酸较不稳定。这种事实与Mitsuhashi对于内酯环稳定性实验甚相符合。

By treatment with ethyl-alcoholic HCl, it was possible to eliminate from the four desmo troposantonins (A, B, C, D) the asymmetric centers at C5 and C6, giving compounds having only one asymmetric center at C11. With the antipodes so obtained, (Ⅳ) and (Ⅴ), it was possible to prove that the disagreement observed on the desmotroposantonins for optical change resulting from alkali inversion was really due to the vicinal effect(see p. 493, B→C and D→A), and further that an experimental proof was offered for the mechanism of the acid inversion of the desmotroposantonins.