1,3-dihydroxy-5-[(Z)-non-2'-enyl]benzene | 253158-28-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 1,3-dihydroxy-5-[(Z)-non-2'-enyl]benzene
• 英文别名: 1,3-dihydroxy-5-[(Z)-2'-nonenyl]benzene；5-[(2Z)-non-2-en-1-yl]benzene-1,3-diol；5-(Z)-non-2-enyl-benzene-1,3-diol；climacostol；5-[(Z)-non-2-enyl]benzene-1,3-diol
• CAS: 253158-28-0
• 化学式: C₁₅H₂₂O₂
• 分子量: 234.338
• InChiKey: VKWFGJNPZKSIEL-FPLPWBNLSA-N

物化性质

• 沸点：
  374.2±17.0 °C(Predicted)
• 密度：
  1.026±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3,5-二羟基苯甲醛 在 咪唑 、 正丁基锂 、 dicobalt octacarbonyl 、 氟化氢吡啶 作用下， 以 四氢呋喃 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.5h， 生成 1,3-dihydroxy-5-[(Z)-non-2'-enyl]benzene
  参考文献：
  名称：

  Climacostol, a defense toxin of the heterotrich ciliate Climacostomum virens against predators

  摘要：

  A toxic substance (climacostol) of the protozoan ciliate Climacostomum virens against the predatory ciliate Dileptus margaritifer was established as 1,3-dihydoxy-5-[(Z)-2'-nonenyl]benzene. The structure was rigorously confirmed by the total synthesis. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01722-0

文献信息

• A Straightforward Diastereoselective Synthesis and Evaluation of Climacostol, A Natural Product with Anticancer Activities
  作者：Enrico Marcantoni、Claudio Ortenzi、Dennis Fiorini、Sandra Giuli、Luana Quassinti、Massimo Bramucci、Consuelo Amantini、Giorgio Santoni、Federico Buonanno

  DOI：10.1055/s-0029-1218695

  日期：2010.5

  basis of continued interest in plant-derived natural products as anticancer agents, a shorter and more efficient synthesis of climacostol is reported. This compound showed an anticancer activity better than that of the natural product. The improved potency and selectivity can be due to the absence of traces of the undesired E-isomer present in the natural climacostol. Furthermore, the versatile strategy

  基于对植物来源的天然产物作为抗癌剂的持续关注，据报道，更短和更有效的合成西莫古丁醇。该化合物显示出比天然产物更好的抗癌活性。效能和选择性的提高可以归因于天然金刚烷醇中不存在痕量的不需要的E-异构体。此外，针对这种简单分子（如climacostol）开发的通用策略可以帮助合成其他更复杂的天然产物。 生物有机化学-CC键形成-非对映选择性-天然产物-保护基-Wittig反应
• Simple Synthesis of Climacostol, a Defensive Secretion by the Ciliate Climacostomum virens
  作者：Yumi ABE、Kenji MORI

  DOI：10.1271/bbb.65.2110

  日期：2001.1

  Climacostol 1,3-dihydroxy-5-[(Z)-2'-nonenyl]benzene,1}, a defensive secretion by the protozoan ciliate Climacostomum virens against predators, was synthesized in a 43% overall yield in three steps by starting from methyl 1,3-bis(tert-butyldimethylsilyloxy) phenylacetate (3).

  Climacostol 1,3-二羟基-5-[(Z)-2'-壬烯基]苯，1}是原生动物纤毛虫 Climacostomum virens 对抗捕食者的一种防御性分泌物，该物质以 1,3-双（叔丁基二甲基硅氧基）苯乙酸甲酯（3）为起点，分三步合成，总收率为 43%。
• Climacostol, a defense toxin of Climacostomum virens (protozoa, ciliata), and its congeners
  作者：Miyuki Eiraku Masaki、Shouji Hiro、Yoshinosuke Usuki、Terue Harumoto、Masayo Noda Terazima、Federico Buonanno、Akio Miyake、Hideo Iio

  DOI：10.1016/j.tet.2003.09.105

  日期：2004.8

  Climacostol (1), a defense toxin of the heterotrich ciliate Climacostomum virens was established as 5-(Z)-non-2-enyl-benzene-1,3-diol. The structure was rigorously confirmed by the total synthesis. The two congeners of climacostol contained in this ciliate were determined as 5-(Z,Z)-undeca-2,5-dienyl-benzene-1,3-diol (2) and 5-(Z,Z,Z)-undeca-2,5,8-trienyl-benzene-1,3-diol (3). (C) 2004 Elsevier Ltd. All rights reserved.