Serratenediol-3 acetat | 35302-52-4

• 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: Serratenediol-3 acetat
• 英文别名: Serratendiol-3-acetat；[(3S,6R,8S,11R,12S,15S,16R,19S,21R)-19-hydroxy-3,7,7,11,16,20,20-heptamethyl-8-pentacyclo[13.8.0.03,12.06,11.016,21]tricos-1(23)-enyl] acetate
• CAS: 35302-52-4
• 化学式: C₃₂H₅₂O₃
• 分子量: 484.763
• InChiKey: JTMRPEBSVBAWGS-HOZQILAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  35
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Serratenediol-3 acetat 在 calcium sulfate 、 氢氧化钾 、 sodium tetrahydroborate 、 sodium acetate 、 氰化汞 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 吡啶 、 甲醇 、 硝基甲烷 、 二氯甲烷 为溶剂， 反应 50.67h， 生成 inundoside-A tetraacetate
  参考文献：
  名称：

  Tsuda, Yoshisuke; Haque, Md. Ekramul, Chemical and pharmaceutical bulletin, 1982, vol. 30, # 4, p. 1500 - 1503

  摘要：

  DOI：

文献信息

• Triterpenoid chemistry. III. Stereospecific reactions of triterpenoid 1,3-glycol monotoslyates and ketotosylates.
  作者：YOSHISUKE TSUDA、KIMIAKI ISOBE、TAKEHIRO SANO、AKIRA MORIMOTO

  DOI：10.1248/cpb.23.98

  日期：——

  The reactions of 1, 3-glycol monotosylates of the configurations A-D with base and LAH were discussed. On reaction with t-butoxide, A and D (cis relationship between-OH and -CH2OTs) gave oxetanes E and F respectively, while B and C (trans relationship between these groups) gave the same seco-aldehyde G. On LAH reduction, in addition to the above reaction (oxetane formation from A and D, seco-alcohol formation from B and C), two further reactions took place ; a) S-O fission (formation of the glycols A-D), and b) C-O fission (formation of the deoxy-compounds H and I), for the latter reaction the cyclic intermediate (K-M) were proposed. The monotosylate of B did not give deoxy-compound. The corresponding keto-tosylate (N and O), when treated with lithium aluminum hydride firstly gave 3β-alcohols (A and C) which are further reduced as above ; the fact which therefore opened a way to yield deoxy-compound (I) from type B glycol (B→N→I).

  讨论了构型为 A-D 的 1，3-乙二醇单甲苯磺酸盐与碱和 LAH 的反应。与叔丁醇反应时，A 和 D（OH 和 -CH2OT 之间的顺式关系）分别生成氧杂环丁烷 E 和 F，而 B 和 C（这些基团之间的反式关系）生成相同的仲醛 G。在 LAH 还原过程中，除了上述反应（由 A 和 D 生成氧杂环丁烷，由 B 和 C 生成仲醇）外，还发生了两个反应：a）S-O 裂变（生成乙二醇 A-D）；b）C-O 裂变（生成脱氧化合物 H 和 I）。B 的单甲苯磺酸盐没有生成脱氧化合物。相应的酮基对甲苯磺酸盐（N 和 O）用氢化铝锂处理后，首先生成 3β 醇（A 和 C），然后再按上述方法进一步还原；因此，这为从 B 型乙二醇（B→N→I）中生成脱氧化合物（I）开辟了道路。
• The Structure of Serratenediol.
  作者：Yasuo Inubushi、Yoshisuke Tsuda、Takehiro Sano、Takeshi Konita、Sachiko Suzuki、Hiroyuki Ageta、Yoshiyuki Otake

  DOI：10.1248/cpb.15.1153

  日期：——

  Retropinacol rearrangement of serratenediol established that either terminal ring of this triterpenoid has the partial structure (A). The accumulated chemical and spectroscopic evidences have been summarized in the structure and stereochemistry (1__=) containing sevenmembered ring for serratenediol, which was confirmed by further degradation into a tricyclic ketone (4__=7__=). The synthesis of this key product has now been achieved. The manner of acid isomerization of serratene derivatives has been also clarified. Serratenediol monoacetate, a minor triterpenoid constituent of Lycopodium serratum, was also established as (3__=), based on ORD examination of various ketonic derivatives.

  对锯齿二醇的Retropinacol重排证实，这种三萜类化合物两个末端环都具有部分结构（A）。 化学和光谱学证据的积累已总结为锯齿二醇的七元环结构和立体化学（1__=），这已通过进一步降解为三环酮（4__=7__=）得到证实。 这种关键产品的合成现在已经实现。 锯齿衍生物的酸异构化方式也已得到澄清。 根据ORD对各种酮类衍生物的检测，锯齿二醇单乙酸酯（一种锯齿石松的三萜类小成分）也被确定为（3__=）。
• Lycopodium triterpenoids. VIII. The structures of lycoclavanin, a triterpenoid-tetraol possessing conjugated ketone chromophor, and a new tetraol, lyclaninol.
  作者：YOSHISUKE TSUDA、TAKUNORI FUJIMOTO、AKIRA MORIMOTO、TAKEHIRO SANO

  DOI：10.1248/cpb.23.1336

  日期：——

  Lycoclavanin, a Lycopodium triterpenoid containing four hydroxy-groups and a conjugated ketone, was established as 16-oxoserrat-14-ene-3α, 20β, 21β, 24-tetraol (7a) by spectral and chemical means. Correlations of lycoclavanin with 16-oxo-lycoclavanol (6a) and with serratenediol (17a) were described. A new tetraol occurring in L. clavatum was also established as serrat-14-ene-3α, 20β, 21β, 24-tetraol (23a).

  通过光谱和化学手段，将石松三萜类化合物石松素（Lycoclavanin）确定为16-氧代石松-14-烯-3α, 20β, 21β, 24-四醇（7a）。描述了石松素与16-氧代石松醇（6a）和石松二醇（17a）的相关性。在石松中存在的一种新的四醇也被确定为serrat-14-ene-3α, 20β, 21β, 24-tetraol（23a）。
• Triterpenoids of Lycopodium megastachyum
  作者：Noah Miller、Claude Hootele、Jean-Claude Braekman

  DOI：10.1016/0031-9422(73)80398-x

  日期：1973.7

  Abstract Eight triterpenes of the serratane type have been isolated from Lycopodium megastachyum Baker. They are serratenediol, 21- epi -serratenediol, serratenediol-3-acetate, 21- epi -serratenediol-3-acetate, lycoclavanol, tohogenol diacetate, phlegmanol-D and serratenonediol diacetate.

  摘要 从Lycopodium megastachyum Baker 中分离得到8 种锯齿烷型三萜。它们是serratenediol、21-epi-serratenediol、serratenediol-3-acetate、21-epi-serratenediol-3-acetate、lycoclavanol、tohogenol diacetate、phlegmanol-D和serratenonediol diacetate。