3β,14-dihydroxy-14β,17βH-pregn-5-ene-11,15,20-trione | 24186-10-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 3β,14-dihydroxy-14β,17βH-pregn-5-ene-11,15,20-trione
• 英文别名: 3β,14-Dihydroxy-14β,17βH-pregn-5-en-11,15,20-trion；α-Digiprogenin；(3S,8R,9S,10R,13R,14S,17R)-17-acetyl-3,14-dihydroxy-10,13-dimethyl-1,2,3,4,7,8,9,12,16,17-decahydrocyclopenta[a]phenanthrene-11,15-dione
• CAS: 24186-10-5
• 化学式: C₂₁H₂₈O₅
• 分子量: 360.45
• InChiKey: HHYUGCQBWAMDLS-CSWSDLTMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  91.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (3S,8R,9S,10R,13R,14S,17S)-17-acetyl-3-[(2R,3R,4S,5S,6R)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy-14-hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,12,16,17-decahydrocyclopenta[a]phenanthrene-11,15-dione 生成 3β,14-dihydroxy-14β,17βH-pregn-5-ene-11,15,20-trione
  参考文献：
  名称：

  Satoh,D., Chemical and pharmaceutical bulletin, 1960, vol. 8, p. 270 - 272

  摘要：

  DOI：

文献信息

• Studies on Digitalis Glycosides. XII. Structures of Digipronin and Digiprogenin.
  作者：Daisuke Satoh

  DOI：10.1248/cpb.10.43

  日期：——

  Digipronin, a digitanol glycoside, and its aglycone, γ-digiprogenin, were respectively converted to isodigipronin and its aglycone, α-digiprogenin, by treatment with dilute alkali or acid. On refluxing with acid, α-digiprogenin lost an element of water and formed β-digiprogenin. The structure of the ⊿4-3-oxo compound, obtained from β-digiprogenin by reduction with acetic acid and zinc dust followed by Oppenauer oxidation, was established as 14β, 17α-pregn-4-ene-3, 11, 15, 20-tetrone by comparison with the product of isomerization of pregn-4-ene-3, 11, 15, 20-tetrone with alkali or acid. Consequently, the structure of β-digiprogenin was presumed as 3β-hydroxy-14β-pregna-5, 16-diene-11, 15, 20-trione and the tertiary hydroxyl group in α-and γ-digiprogenin would be located at 17-position. In view of the stability of α-digiprogenin to dilute alkali or acid and its negative contribution to optical rotation compared to γ-digiprogenin, it would be appropriate to give the structure of 3β, 17α-dihydroxy-14β-pregn-5-ene-11, 15, 20-trione and 3β, 17α-dihydroxypregn-5-ene-11, 15, 20-trione to α-and γ-digiprogenin, respectively. Digipronin is a monodigitaloside of γ-digiprogenin.

  通过稀碱或稀酸的处理，地吉孕宁（地吉孕酚苷）及其苷元--γ-地吉孕宁分别转化为异地吉孕宁及其苷元--α-地吉孕宁。用酸回流时，α-二脂原素失去了水元素，形成了 β-二脂原素。通过与孕-4-烯-3，11，15，20-四酮与碱或酸异构化的产物进行比较，从 β-二脂原素中用乙酸和锌粉还原，再用奥普瑙尔氧化法得到的⊿4-3-氧代化合物的结构被确定为 14β，17α-孕-4-烯-3，11，15，20-四酮。因此，β-二脂原蛋白的结构被推测为 3β-hydroxy-14β-pregna-5, 16-diene-11, 15, 20-triione，而 α 和 γ-二脂原蛋白中的叔羟基将位于 17 位。鉴于α-二降头素对稀碱或稀酸的稳定性，以及与γ-二降头素相比它对光学旋转的负作用，将 3β，17α-二羟基-14β-孕甾-5-烯-11，15，20-三酮和 3β，17α-二羟基孕甾-5-烯-11，15，20-三酮的结构分别赋予α-和γ-二降头素是合适的。地吉孕宁是γ-地吉孕宁的单二萜苷。
• Satoh et al., Chemical and pharmaceutical bulletin, 1966, vol. 14, p. 552
  作者：Satoh et al.

  DOI：——

  日期：——