terricollene C | 942433-95-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: terricollene C
• 英文别名: p-hydroxymethylphenyl 2,3-butadienyl ether
• CAS: 942433-95-6
• 化学式: C₁₁H₁₂O₂
• 分子量: 176.215
• InChiKey: LUYBTTHXSOULBZ-UHFFFAOYSA-N

物化性质

• 沸点：
  322.1±22.0 °C(Predicted)
• 密度：
  1.033±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  terricollene C 在 碘 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 1-buta-2,3-dienyloxy-4-iodomethylbenzene
  参考文献：
  名称：

  Synthesis and biological evaluation of 12 allenic aromatic ethers

  摘要：

  Twelve allenic aromatic ethers, some of them are natural products isolated from the mangrove fungus Xylaria sp. 2508 in the South China Sea, were synthesized. Their antitumor activities against KB and KBv200 cells were determined. All these compounds demonstrated cytotoxic potential, ranging from weak to strong activity. The analysis of structure-activity relationships suggested that the introduction of allenic moiety could generate or enhance cytotoxicity of these phenol compounds. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.02.084
• 作为产物：
  描述：

  4-bromo-buta-1,2-diene 、 对羟基苯甲醇 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以84%的产率得到terricollene C
  参考文献：
  名称：

  Synthesis and biological evaluation of 12 allenic aromatic ethers

  摘要：

  Twelve allenic aromatic ethers, some of them are natural products isolated from the mangrove fungus Xylaria sp. 2508 in the South China Sea, were synthesized. Their antitumor activities against KB and KBv200 cells were determined. All these compounds demonstrated cytotoxic potential, ranging from weak to strong activity. The analysis of structure-activity relationships suggested that the introduction of allenic moiety could generate or enhance cytotoxicity of these phenol compounds. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.02.084

文献信息

• A palladium-catalyzed approach to allenic aromatic ethers and first total synthesis of terricollene A
  作者：Chaofan Huang、Fuchun Shi、Yifan Cui、Can Li、Jie Lin、Qi Liu、Anni Qin、Huanan Wang、Guolin Wu、Penglin Wu、Junzhe Xiao、Haibo Xu、Yuan Yuan、Yizhan Zhai、Wei-Feng Zheng、Yangguangyan Zheng、Biao Yu、Shengming Ma

  DOI：10.1039/d1sc01896e

  日期：——

  3-allenic aromatic ethers with decent to excellent yields under mild reaction conditions has been described. A variety of synthetically useful functional groups are tolerated and the synthetic utility of this method has been demonstrated through a series of transformations of the allene moiety. By applying this reaction as the key step, the total syntheses of naturally occurring allenic aromatic ethers

  描述了在温和的反应条件下，钯催化的苯酚和烯基碳酸酯之间的 C-O 键形成反应，以良好的收率生成 2,3-烯基芳香族醚。可以耐受多种合成上有用的官能团，并且该方法的合成效用已通过丙二烯部分的一系列转化得到证明。以该反应为关键步骤，完成了天然烯属芳香醚、桉烯和土三烯A的全合成（首次合成；4.5克规模）。