(1S,4S,4aR,7aS,7bR)-1,4,4a,5,6,7,7a,7b-Octahydro-1,4-dihydroxy-3-hydroxymethyl-6,6,7b-trimethyl-2H-cyclobut[e]inden-2-one

• 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: (1S,4S,4aR,7aS,7bR)-1,4,4a,5,6,7,7a,7b-Octahydro-1,4-dihydroxy-3-hydroxymethyl-6,6,7b-trimethyl-2H-cyclobut[e]inden-2-one
• 英文别名: Tsugicoline A；(1S,4S,4aR,7aS,7bR)-1,4-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1,4,4a,5,7,7a-hexahydrocyclobuta[e]inden-2-one
• 化学式: C₁₅H₂₂O₄
• 分子量: 266.337
• InChiKey: PAMKMSXEULAYKN-TZBUPLKMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,4S,4aR,7aS,7bR)-1,4,4a,5,6,7,7a,7b-Octahydro-1,4-dihydroxy-3-hydroxymethyl-6,6,7b-trimethyl-2H-cyclobut[e]inden-2-one 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以79%的产率得到5-epi-tsugicoline C
  参考文献：
  名称：

  Protoilludane sesquiterpenoids as scaffold structures for new antimicrobials against Mannheimia haemolytica

  摘要：

  DOI：

  10.1038/ja.2012.90

文献信息

• Secondary mould metabolites. Part 58. Modifications in basic conditions and Michael additions of the protoilludane sesquiterpene tsugicoline A; some implications for the biogenesis of other sesquiterpenoids produced by Basidiomycetes
  作者：Alberto Arnone、Cristiana De Gregorio、Andrea Mele、Gianluca Nasini、Orso Vajna de Pava

  DOI：10.1039/a908912h

  日期：——

  The protoilludane sesquiterpene tsugicoline A 1 rearranges at pH 13 into compound 8a with a structure very similar to isolactarane sesquiterpenes and into compound 9a similar to the natural furosesquiterpene tsugicoline H 9c; under different basic conditions compounds 4a, 5, 6a and 7a,b, are formed. In particular, 4a shows the same skeleton of the natural tsugicoline E 4c. Compound 1 reacts with some thiols to give a Michael addition to α,β-conjugated carbonyl system, giving the adducts 10–13. In the case of compounds 12a,b a new tetrahydrothiophene ring is formed. The structures and stereochemistry of the products are discussed with the aid of NMR data; compounds 4a,c, 10 and 12a,b are correlated also with tandem MS studies. The implications of these results on current opinions on the biogenetic pathways of sesquiterpenes of Basidiomycetes are discussed.

  原illudane 倍半萜sugicoline A 1 在 pH 值为 13 时重新排列为化合物 8a，其结构与 isolactarane 倍半萜非常相似，并重新排列为与天然呋喃倍半萜sugicoline H 9c 相似的化合物 9a；在不同的碱性条件下，形成化合物 4a、5、6a 和 7a,b。其中，4a 的骨架与天然sugicoline E 4c 相同。化合物 1 与一些硫醇发生反应，与 α、β-共轭羰基体系发生迈克尔加成反应，生成加合物 10-13。在化合物 12a,b 中，形成了一个新的四氢噻吩环。借助核磁共振数据对产物的结构和立体化学进行了讨论；化合物 4a,c、10 和 12a,b 还与串联质谱研究相关联。讨论了这些结果对目前有关玄参属倍半萜生物遗传途径的观点的影响。
• Isolation and structure elucidation of tsugicolines A-D, novel protoilludane sesquiterpenes from Laurilia tsugicola1
  作者：Alberto Arnone、Umberta Brambilla、Gianluca Nasini、Orso Vajna de Pava

  DOI：10.1016/0040-4020(95)00848-3

  日期：1995.11

  Four novel Sesquiterpenes, tsugicolines A-D (1a, 2, 3a, 4), have been isolated from still cultures of the fungus Laurilia tsugicola (Basidiomycetae) Their structures were elucidated by means of chemical correlations and NMR studies and the relative configurations were established through a series of NOE difference spectra. The absolute configuration of tsugicoline A 1a (3-epi-illudol-5-one) was determined

  从真菌Laurilia tsugicola（Basidiomycetae）的静止培养物中分离出四种新的倍半萜，tsugicolines AD（1a，2，3a，4）。系列NOE差异谱。通过Horeau用甲醇中的三乙胺对Horkico进行处理的tsuegicoline A 1a的“部分拆分”方法，将tsugicoline A 1a（3- epi -illudol-5-one）的绝对构型确定为3S，6S，7R，9R，13S。代谢物4; 报告了一种可能的机制。Tsugicoline A对细菌和真菌没有活性，但能抑制水芹Lepidium sativum的发芽。
• Arnone, Alberto; De Gregorio, Cristiana; Nasini, Gianluca, Journal of the Chemical Society. Perkin transactions I, <hi>1997</hi>, # 10, p. 1523 - 1525
  作者：Arnone, Alberto、De Gregorio, Cristiana、Nasini, Gianluca、Vajna De Pava, Orso

  DOI：——

  日期：——
• Protoilludane sesquiterpenoids as scaffold structures for new antimicrobials against Mannheimia haemolytica
  作者：Gemma Assante、Sabrina Dallavalle、Piera Anna Martino

  DOI：10.1038/ja.2012.90

  日期：2013.1