(-)-compressanolide | 68421-48-7

• 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: (-)-compressanolide
• 英文别名: Compressanolide；(3S,3aS,6aR,9R,9aS,9bS)-9-hydroxy-3,9-dimethyl-6-methylidene-3a,4,5,6a,7,8,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2-one
• CAS: 68421-48-7
• 化学式: C₁₅H₂₂O₃
• 分子量: 250.338
• InChiKey: JFSCVRCZWCVAOQ-XTXFXJEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  (-)-compressanolide 在 sodium hydroxide 、 二甲基硫 、 臭氧 作用下， 以 甲醇 为溶剂， 反应 5.17h， 生成 (3S,3aS,6aS,9R,9aS,9bS)-9-Hydroxy-3,9-dimethyl-decahydro-azuleno[4,5-b]furan-2,6-dione
  参考文献：
  名称：

  The biomimetic synthesis of trans-(1β-h,5α-h)-guaianolides

  摘要：

  DOI：

  10.1016/s0040-4020(01)86160-3
• 作为产物：
  描述：

  1β,4α-dihydroxy-3α,11β-H-eudesman-6α,12-olide 在 potassium acetate 作用下， 以 吡啶 、 溶剂黄146 为溶剂， 反应 98.0h， 生成 (-)-compressanolide
  参考文献：
  名称：

  Biomimetic cyclization of gallicin to form guaianolides

  摘要：

  DOI：

  10.1016/0040-4020(80)80216-x

文献信息

• Parthenolide and its photochemically synthesized 1(10) Z isomer: chemical reactivity and structure–activity relationship studies in human leucocyte chemotaxis
  作者：Hannes Neukirch、Nicole C Kaneider、Christian J Wiedermann、Antonio Guerriero、Michele D'Ambrosio

  DOI：10.1016/s0968-0896(02)00553-9

  日期：2003.4

  germacrolide into a melampolide. The investigation on their chemical properties allowed us to evaluate the minimum interatomic distance needed for transannular bridging of C(10) ring in germacrolides and to explain the regiochemical selectivity of electrophilic cyclizations. The antiinflammatory activity of parthenolide and its semisynthetic derivatives was evaluated by in vitro chemotaxis assay with human neutrophiles

  目前的研究已经实现了杀菌剂金葡糖胺的光化学转化为聚丙烯酰胺。对它们的化学性质的研究使我们能够评估杀菌棒中C（10）环跨环桥接所需的最小原子间距离，并解释了亲电环化的区域化学选择性。通过对人嗜中性白细胞的体外趋化性分析评估了小白菊内酯及其半合成衍生物的抗炎活性。这些结构-活性关系研究导致了一种新的药效团的假设，并为计算设计的药物提供了有用的信息。
• Stereoselective Synthesis of (+)-11<b>β</b><i>H</i>,13-Dihydroestafiatin, (+)-11<b>β</b><i>H</i>,13-Dihydroludartin, (−)-Compressanolide, and (−)-11<b>β</b><i>H</i>,13-Dihydromicheliolide from Santonin
  作者：Victoria Bargues、Gonzalo Blay、Luz Cardona、Begoña García、José R. Pedro

  DOI：10.1021/np020109f

  日期：2002.11.1

  Starting from 2 and 3, obtained from santonin (1), we have synthesized natural guaianolides 4-7. Chemoselective epoxidation of 2 gave (+)-11betaH,13-dihydroestafiatin (4), and epoxidation of 3 followed by regioselective elimination of the hydroxyl group afforded (+)-11betaH,13-dihydroludartin (5). Sharpless' mild regioselective ring-opening of 4 and 5 followed by hydrogenolysis yielded (-)-compressanolide (6) and (-)-11betaH,13-dihydromicheliolide (7), respectively.
• Antimycobacterial evaluation of germacranolides in honour of professor G.H. Neil Towers 75th birthday
  作者：Nikolaus H. Fischer、Tiansheng Lu、Charles L. Cantrell、José Castañeda-Acosta、Leovigildo Quijano、Scott G. Franzblau

  DOI：10.1016/s0031-9422(98)00253-2

  日期：1998.9

  The minimum inhibitory concentrations (MIC) against Mycobacterium tuberculosis and M. avium of parthenolide, costunolide, 1 (10)-epoxycostunolide and other germacranolide-type sesquiterpene lactones and derivatives were determined by use of a radiorespirometric bioassay. Structure-activity relationship studies with natural and semisynthetic sesquiterpene lactones suggested that the alpha-methylene-gamma-lactone moiety is an essential, but not sufficient, structural requirement for significant in vitro activity against M. tuberculosis and M. avium. (C) 1998 Elsevier Science Ltd. All rights reserved.
• PARODI, FELIX J.;FRONCZEK, FRANK R.;FISCHER, NIKOLAUS H., J. NATUR. PROD., 52,(1989) N, C. 554-566
  作者：PARODI, FELIX J.、FRONCZEK, FRANK R.、FISCHER, NIKOLAUS H.

  DOI：——

  日期：——
• GONZALEZ, ANTONIO G.;GALINDO, ANTONIO;AFONSO, M. MAR;MANSILLA, HORACIO;PA+, TETRAHEDRON, 44,(1988) N 14, C. 4575-4584
  作者：GONZALEZ, ANTONIO G.、GALINDO, ANTONIO、AFONSO, M. MAR、MANSILLA, HORACIO、PA+

  DOI：——

  日期：——