Tetraacetyl-7-ketologanin | 20586-14-5

• 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: Tetraacetyl-7-ketologanin
• 英文别名: 7-Dehydrologanin tetraacetate；methyl (1S,4aS,7R,7aS)-7-methyl-6-oxo-1-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-4a,5,7,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylate
• CAS: 20586-14-5
• 化学式: C₂₅H₃₂O₁₄
• 分子量: 556.521
• InChiKey: WXNZYXJASJZABT-SIDXAJJHSA-N

物化性质

• 沸点：
  615.9±55.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  39
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  176
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  Tetraacetyl-7-ketologanin 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 7-ketologanin
  参考文献：
  名称：

  木犀科类环烯醚萜苷的生物合成

  摘要：

  摘要 油苷类糖苷（油苷）的生物合成已在木犀科的两种植物中进行了研究，即精益白蜡和丁香。制备了脱氧木酸、8-表-脱氧木酸、7-表-脱氧木酸和木糖酸的氘代类似物。在施用上述化合物时，获得了高掺入的脱氧原酸以及原木酸及其 7-差向异构体，这强烈暗示 7-酮基酸是油苷生物合成中的中间体。 . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 通过 2 H NMR 测量了几种分离的类环烯醚萜烯中的掺入量，这些类环烯脂酸酯均属于油苷。此外，还检测了另外两种木犀科植物 Ligustrum Ollifolium 和 Phillyrea

  DOI：

  10.1016/0031-9422(91)80018-v
• 作为产物：
  描述：

  马钱子苷 在 jones reagent 作用下， 以 吡啶 为溶剂， 生成 Tetraacetyl-7-ketologanin
  参考文献：
  名称：

  Raj; Mathad, Vijayavitthal T.; Bhaduri, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1996, vol. 35, # 10, p. 1056 - 1061

  摘要：

  DOI：

文献信息

• Absolute structure of nepetaside, a new iridoid glucoside from Nepeta cataria
  作者：Shan Xie、Shinichi Uesato、Hiroyuki Inouye、Tetsuro Fujita、Fujio Murai、Motoko Tagawa、Tetsuro Shingu

  DOI：10.1016/0031-9422(88)83122-4

  日期：1988.1

  Abstract Besides an earlier reported 1,5,9-epideoxyloganic acid, a new iridoid glucoside, nepetaside, has been isolated from the aerial part of Nepeta cataria . Its absolute structure has been elucidated based on NMR spectroscopy and chemical conversions.

  摘要 除了早先报道的1,5,9-环氧木酸外，还从荆芥的地上部分分离到了一种新的环烯醚萜苷，荆芥苷。其绝对结构已基于核磁共振光谱和化学转化得到阐明。
• Intermediacy of 6-hydroxyloganin in the ring cleavage course of loganin to secologanin
  作者：Kenichiro Inoue、Takao Tanahashi、Hiroyuki Inouye、Hiroshi Kuwajima、Kiyokazu Takaishi

  DOI：10.1016/0031-9422(89)80263-8

  日期：1989.1

  Abstract A possible biosynthetic pathway from loganin to secologanin through ring cleavage of 6-hydroxyloganin was ruled out in feeding experiments in which Eustoma russellianum , Swertia japonica , Lonicera morrowii and Adina pilulifera were each presented with three C-6 and C-7 stereoisomers of 6-hydroxy [7- 2 H] loganin as well as [6,6,7,8- 2 H 4 ] - and [6,6,7,8 carbomethoxy- 2 H 7 ]-loganin. In

  摘要 在饲喂实验中排除了从马钱素通过 6-羟基马钱素的环裂解到赛洛加宁的可能生物合成途径，其中罗素、獐牙、忍冬和阿迪娜分别具有 6 种 C-6 和 C-7 立体异构体。 -羟基[7- 2 H]马钱素以及[6,6,7,8- 2 H 4 ] - 和[6,6,7,8 甲氧基-2 H 7 ]-马钱素。在相关实验中，导致 seroside 的 secologanin 醛基的还原被证明是通过来自 si 面的氢化物离子攻击进行的。
• Biosynthesis of secoiridoids in Fontanesia
  作者：Søren Damtoft、Henrik Franzyk、Søren Rosendal Jensen

  DOI：10.1016/0031-9422(94)00683-k

  日期：1995.2

  Abstract Fontanesia fortunei was found to contain the new secoiridoid glucoside 7- E / Z -( p -coumaroyl)-5-hydroxysecologanol together with the known compounds secologanic acid, secologanol, secologanoside, fontanesioside, verbascoside and chlorogenic acid. This secoiridoid profile is different from that found in other known genera of the Oleaceae, since no oleoside-derived compounds were present

  摘要 Fontanesia Fortunei 被发现含有新的类环烯醚萜苷 7-E/Z-(p-香豆酰基)-5-羟基环十二烷醇以及已知化合物环十二烷酸、环十二烷醇、环十二烷苷、枫烷西苷、毛蕊花苷和绿原酸。由于不存在油苷衍生的化合物，因此这种类环烯醚萜的特征与在木犀科其他已知属中发现的特征不同。将氘标记的脱氧罗根酸、7-表-罗根酸和罗根酸施用于 F.fortunei 和 F.phillyreoides，并通过 2 H NMR 测量两种植物中的癸二酸。
• Biosynthesis of iridoids in Syringa and Fraxinus: Secoiridoid precursors
  作者：Søren Damtoft、Henrik Franzyk、Søren Rosendal Jensen

  DOI：10.1016/0031-9422(95)00211-o

  日期：1995.10

  Several deuterium-labelled secoiridoids have been prepared and tested as possible precursors for the iridoids in Fraxinus excelsior, Syringa josikaea and S. vulgaris. Oleoside Ii-methyl ester was an efficient precursor for the oleosides, whereas secologanin-type iridoids gave only significant incorporation in 5. josikaea. In this plant low incorporations into the oleosides were also seen for kingiside and 8-epi-kingiside. The major pathway to the oleosides therefore seems to proceed via a direct ring fission of ketologanin to oleoside 11-methyl ester. A Baeyer-Villiger-like mechanism which explains the different compounds found in the plants is proposed, and the taxonomy of the Oleaceae is discussed. Due to the unique presence of the usual pathway leading to secologanin and its congeners in Fontanesia, the Oleaceae is considered to be a member of the Gentiananae rather than Scrophulariales/Lamianae.
• INOUE, KENICHIRO;TANAHASHI, TAKAO;INOUYE, HIROYUKI;KUWAJIMA, HIROSHI;TAKA+, PHYTOCHEMISTRY, 28,(1989) N1, C. 2971-2979
  作者：INOUE, KENICHIRO、TANAHASHI, TAKAO、INOUYE, HIROYUKI、KUWAJIMA, HIROSHI、TAKA+

  DOI：——

  日期：——