trixagol | 69903-57-7

• 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: trixagol
• 英文别名: (2E,6E)-9-[(1S)-2,2-dimethyl-6-methylene-cyclohexyl]-3,7-dimethyl-nona-2,6-dien-1-ol；(2E,6E)-9-[(1S)-2,2-dimethyl-6-methylidenecyclohexyl]-3,7-dimethylnona-2,6-dien-1-ol
• CAS: 69903-57-7
• 化学式: C₂₀H₃₄O
• 分子量: 290.489
• InChiKey: YHXQJKUUMBTWSB-SOXCBWEDSA-N

物化性质

• 沸点：
  386.0±11.0 °C(Predicted)
• 密度：
  0.91±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  trixagol 在 三溴化磷 、 溶剂黄146 、 锌 作用下， 以 甲醇 、 乙醚 、 N,N-二甲基乙酰胺 为溶剂， 反应 39.0h， 生成 (S)-(2'E,6'E)-6-amino-9-methyl-7-[(2,2-dimethyl-6-methylenecyclohexyl)-3,7-dimethyl-2,6-nonadien-1-yl]-7H-purinium chloride
  参考文献：
  名称：

  月桂碱E及其类似物的合成及其抗分枝杆菌活性。

  摘要：

  Agelasine E以前是从海洋海绵Agelas nakamurai中分离出来的，它是与具有各种萜类侧链的类似物一起首次合成的。用烯丙基溴处理N6-甲氧基-9-甲基-9H-嘌呤-6-胺，得到所需的7,9-二烷基pur盐以及少量的N6-烷基化异构体。最后，N6-甲氧基被还原性除去。1H-15N HMBC和1H-15N HSQC NMR光谱学提供了有关所研究的嘌呤衍生物中互变异构和电荷离域的其他信息。筛选了杂环产物对结核分枝杆菌的活性，在嘌呤7-位带有相对较长的萜类取代基和N-6处的甲氧基基团的长老苷类似物是有效的细菌生长抑制剂。

  DOI：

  10.1039/b417471b
• 作为产物：
  描述：

  (S)-(-)-2,2-dimethyl-6-methylene-1-[1'-(phenylthio)methyl]cyclohexane 在 正丁基锂 、 Oxone 、 4-甲基苯磺酸吡啶 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 为溶剂， 反应 45.0h， 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

文献信息

• Minor components with the γ-cyclogeranil geraniol skeleton from Bellardia trixago (L.) all.
  作者：J.-T.De Pascual、E. Caballero、C. Caballero、M. Medarde、A.F. Barrero、M. Grande

  DOI：10.1016/0040-4020(82)80260-3

  日期：1982.1

  Trixagol 1 and fourteen derivatives with the skeleton of γ-cyclogeranil geraniol were isolated from Bellardia trixago, the structures were determined by spectroscopic methods and confirmed by partial synthesis. Furthermore. 3,4-dihydro-γ-ionone, α-ambrinol, β-sitosterol and three flavonoids 5-O-demethyl tangeretin, 5-hydroxy auranetin and 3′-methoxy calycopterin were also isolated.

  Trixagol 1和14个衍生物与γ-cyclogeranil香叶醇从分离的骨架Bellardia trixago，该结构通过光谱方法测定和通过部分合成证实。此外。还分离出3，4-二氢-γ-紫罗兰酮，α-细溴酚，β-谷甾醇和三种类黄酮5- O-去甲基橘皮苷，5-羟基金刚烷苷和3'-甲氧基蝶呤。
• Preparation of (S)-γ-cyclogeraniol by lipase-catalyzed transesterification and synthesis of (+)-trixagol and (+)-luffarin-P
  作者：Mikio Fujii、Yosuke Morimoto、Machiko Ono、Hiroyuki Akita

  DOI：10.1016/j.molcatb.2015.11.019

  日期：2016.1

  Lipase-catalyzed kinetic resolution of gamma-cyclogeraniol by Candida antarctica lipase B yielded 23% of enantiomerically pure (S)-gamma-cyclogeraniol. (+)-trixagol and (+)-luffarin-P were synthesized from the obtained (S)-gamma-cyclogeraniol, and the absolute configuration of natural (+)-luffarin-P was determined to have an S configuration by our first synthesis of (S)-luffarin-P for the first time. (C) 2015 Elsevier B.V. All rights reserved.
• Synthesis of (+)-trixagol and its enantiomer, the terpenoid side chain of (−)-agelasine E
  作者：Anne Kristin Bakkestuen、Lise-Lotte Gundersen

  DOI：10.1016/s0040-4020(02)01455-2

  日期：2003.1

  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.
• Synthesis and antimycobacterial activity of agelasine E and analogs
  作者：Anne Kristin Bakkestuen、Lise-Lotte Gundersen、Dirk Petersen、Bibigul T. Utenova、Anders Vik

  DOI：10.1039/b417471b

  日期：——

  delocalization in the purine derivatives studied. The heterocyclic products were screened for activity against Mycobacterium tuberculosis and agelasine analogs carrying a relatively long terpenoid substituent in the purine 7-position and a methoxy group at N-6 were potent inhibitors of bacterial growth. Since agelasine analogs with the geranylgeranyl chain at N-7 exhibited antimicrobial activity, several strategies

  Agelasine E以前是从海洋海绵Agelas nakamurai中分离出来的，它是与具有各种萜类侧链的类似物一起首次合成的。用烯丙基溴处理N6-甲氧基-9-甲基-9H-嘌呤-6-胺，得到所需的7,9-二烷基pur盐以及少量的N6-烷基化异构体。最后，N6-甲氧基被还原性除去。1H-15N HMBC和1H-15N HSQC NMR光谱学提供了有关所研究的嘌呤衍生物中互变异构和电荷离域的其他信息。筛选了杂环产物对结核分枝杆菌的活性，在嘌呤7-位带有相对较长的萜类取代基和N-6处的甲氧基基团的长老苷类似物是有效的细菌生长抑制剂。