(2E,6E)-2,6-dimethyl-8-(tetrahydro-2H-pyran-2-yloxy)octa-2,6-dienyl-4-methylbenzenesulfonate | 502763-31-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2E,6E)-2,6-dimethyl-8-(tetrahydro-2H-pyran-2-yloxy)octa-2,6-dienyl-4-methylbenzenesulfonate
• 英文别名: (2E,6E)-3,7-dimethyl-1-(tetrahydro-2-pyranyl)oxy-2,6-octadien-8-yl 4-methylbenzenesulfonate；[(2E,6E)-2,6-dimethyl-8-(oxan-2-yloxy)octa-2,6-dienyl] 4-methylbenzenesulfonate
• CAS: 502763-31-7
• 化学式: C₂₂H₃₂O₅S
• 分子量: 408.559
• InChiKey: CHTYCHOXKAIOMR-SJBLAXMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  70.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2E,6E)-2,6-dimethyl-8-(tetrahydro-2H-pyran-2-yloxy)octa-2,6-dienyl-4-methylbenzenesulfonate 在 正丁基锂 、 4-甲基苯磺酸吡啶 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 42.0h， 生成 trixagol
  参考文献：
  名称：

  Synthesis of (+)-trixagol and its enantiomer, the terpenoid side chain of (−)-agelasine E

  摘要：

  The naturally occurring gamma-cyclogeranylgeraniol called (+)-trixagol has been synthesised for the first time. Trixagol was readily available in five steps from (S)-2,2-dimethyl-6-methylene-1-cyclohexanemethanol. The enantiomer of trixagol, which equates to the terpenoid side chain of the naturally occurring 7,9-dialkylpurinium salt (-)-agelasine E, was prepared from the (R) enantiomer of the cyclohexanemethanol. Both trixagol enantiomers were moderately active against Mycobacterium tuberculosis. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01455-2
• 作为产物：
  描述：

  (2E,6E)-2,6-dimethyl-8-((tetrahydro-2H-pyran-2-yl)oxy)octa-2,6-dien-1-ol 、 对甲苯磺酰氯 在 三甲胺盐酸盐 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以100%的产率得到(2E,6E)-2,6-dimethyl-8-(tetrahydro-2H-pyran-2-yloxy)octa-2,6-dienyl-4-methylbenzenesulfonate
  参考文献：
  名称：

  Synthesis of (+)-trixagol and its enantiomer, the terpenoid side chain of (−)-agelasine E

  摘要：

  The naturally occurring gamma-cyclogeranylgeraniol called (+)-trixagol has been synthesised for the first time. Trixagol was readily available in five steps from (S)-2,2-dimethyl-6-methylene-1-cyclohexanemethanol. The enantiomer of trixagol, which equates to the terpenoid side chain of the naturally occurring 7,9-dialkylpurinium salt (-)-agelasine E, was prepared from the (R) enantiomer of the cyclohexanemethanol. Both trixagol enantiomers were moderately active against Mycobacterium tuberculosis. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01455-2

文献信息

• Synthesis, Antimicrobial and Antineoplastic Activities for Agelasine and Agelasimine Analogs with a β-Cyclocitral Derived Substituent
  作者：Ágnes Proszenyák、Colin Charnock、Erik Hedner、Rolf Larsson、Lars Bohlin、Lise-Lotte Gundersen

  DOI：10.1002/ardp.200700137

  日期：2007.12

  Agelasines and agelasimines are antimicrobial and cytotoxic purine derivatives isolated from marine sponges (Agelas sp.). We have synthesized structurally simplified analogs of these natural products starting from β‐cyclocitral. The novel compounds were found to be strong inhibitors of a wide variety of pathogenic microorganisms (incl. Mycobacterium tuberculosis) as well as cancer cell lines. The biological

  Agelasines 和agelasines 是从海绵（Agelas sp.）中分离出来的抗菌和细胞毒性嘌呤衍生物。我们从 β-环柠檬醛开始合成了这些天然产物的结构简化类似物。发现这些新化合物是多种病原微生物（包括结核分枝杆菌）以及癌细胞系的强抑制剂。生物活性通常与先前发现的结构更复杂的agelasines 和从天然来源中少量分离出来的agelasines 的生物活性相同。我们还首次报告了阿格拉辛和阿格拉西胺类似物抑制原生动物（卡斯特拉米巴棘阿米巴和多食棘阿米巴）的生长。棘阿米巴角膜炎是一种越来越常见和严重的角膜感染，