(16S)-1α,14α-diacetoxy-20-ethyl-6β,16-dimethoxy-4-methoxymethyl-7,17-seco-aconitan-7-one | 17127-46-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (16S)-1α,14α-diacetoxy-20-ethyl-6β,16-dimethoxy-4-methoxymethyl-7,17-seco-aconitan-7-one
• 英文别名: (16S)-1α,14α-diacetoxy-20-ethyl-6β,16-dimethoxy-4-methoxymethyl-7,17-seco-aconitan-7-one；(16S)-1α,14α-Diacetoxy-20-aethyl-6β,16-dimethoxy-4-methoxymethyl-7,17-seco-aconitan-7-on
• CAS: 17127-46-7
• 化学式: C₂₈H₄₃NO₈
• 分子量: 521.651
• InChiKey: JRMNKZNGGXOHSW-CKUJRZNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  37.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  100.6
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (16S)-1α,14α-diacetoxy-20-ethyl-6β,16-dimethoxy-4-methoxymethyl-7,17-seco-aconitan-7-one 生成 (16S)-20-ethyl-1α,14α-dihydroxy-6β,16-dimethoxy-4-methoxymethyl-7,17-seco-aconitan-7-one
  参考文献：
  名称：

  On Lucaconine

  摘要：

  DOI：

  10.1246/bcsj.31.1082
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 溶剂黄146 、 铂 作用下， 生成 (16S)-1α,14α-diacetoxy-20-ethyl-6β,16-dimethoxy-4-methoxymethyl-7,17-seco-aconitan-7-one
  参考文献：
  名称：

  On Lucaconine

  摘要：

  DOI：

  10.1246/bcsj.31.1082

文献信息

• The Aconite Alkaloids. XXXVII. Anhydro-diacetyldelcosine (Anhydrodiacetyllucaconine) and Its Novel Hydrogenation
  作者：Takashi Amiya、Takeo Shima

  DOI：10.1246/bcsj.40.1957

  日期：1967.8

  Delcosine (lucaconine) and its derivatives have all been shown to lose one mole of water, upon treatment with acetyl chloride, thus giving an anhydro compound. On the basis of the observation of the infrared spectra of anhydro-diacetyldelcosine, anhydro-oxodelcosine, and anhydro-1, 10-didehydro-oxodelcosine, it may be concluded that, in each compound, dehydration takes place between two tertiary hydroxyl groups, with a ketone carbonyl group being formed. Based on a tentative structure for delcosine proposed by Marion and his co-workers, structures for anhydro-diacetyldelcosine and anhydro-oxdelcosine are proposed. On hydrogenation over platinum in acetic acid, anhydro-diacetyldelcosine yielded anhydro-dihydro-diacetyl-delcosine. Anhydro-oxodelcosine was inert under these reduction conditions. On the basis of these experimental results, a possible mechanism of this novel hydrogenation is proposed. The ultraviolet spectrum of anhydro-diacetyldelcosine, with a new type of chromophore, is also shown.

  研究表明，当用乙酰氯处理时，Delcosine（露卡宁）及其衍生物都会失去一摩尔的水，从而生成一种脱水化合物。根据对脱水-二乙酰基鹅掌楸碱、脱水-氧代鹅掌楸碱和脱水-1，10-二脱水-氧代鹅掌楸碱红外光谱的观察，可以得出结论：在每种化合物中，两个叔羟基之间都发生了脱水反应，并形成了一个酮羰基。根据马里恩和他的同事们提出的脱氢二乙酰脱氢鹅掌楸碱的暂定结构，提出了脱氢二乙酰脱氢鹅掌楸碱和脱氢氧脱氢鹅掌楸碱的结构。在醋酸中用铂进行氢化时，脱水二乙酰基鹅膏蕈碱生成脱水二乙酰基鹅膏蕈碱。在这些还原条件下，脱水氧代鹅掌楸碱是惰性的。根据这些实验结果，提出了这种新型氢化反应的可能机理。此外，还展示了带有新型发色团的脱水二乙酰基鹅膏蕈碱的紫外光谱。