Eucalyptene A | 149064-39-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: Eucalyptene A
• CAS: 149064-39-1
• 化学式: C₁₄H₁₄O₃
• 分子量: 230.263
• InChiKey: LUTXPQCBZWHPTG-JXMROGBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Eucalyptene A 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 36.0h， 以87%的产率得到but-2,3-dienyl ether of p-hydroxycinnamic acid
  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：

  methyl 4-hydroxycinnamate 在 吡啶 、 氯化亚砜 、 铜 、 sodium hydride 、 锌 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 85.0h， 生成 Eucalyptene A
  参考文献：
  名称：

  来自真菌 Clitocybe eucalyptorum 的两种肉桂醛醚

  摘要：

  摘要 Eucalyptene A 是一种从 Clitocybe eucalyptorum 中分离的真菌代谢物，根据 1 H 和 13 C NMR 证据确定其结构为 4′-(2″,3″-丁二烯氧基) 反式肉桂酸甲酯和化学合成。少量的顺式异构体桉树油 B 也被分离出来。

  DOI：

  10.1016/s0031-9422(00)95105-7

文献信息

• Synthesis and biological evaluation of 12 allenic aromatic ethers
  作者：San-yong Wang、Wei-wei Mao、Zhi-gang She、Chun-rong Li、Ding-qiao Yang、Yong-cheng Lin、Li-wu Fu

  DOI：10.1016/j.bmcl.2007.02.084

  日期：2007.5

  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.
• Two cinnamic allenic ethers from the fungus Clitocybe eucalyptorum
  作者：Alberto Arnone、Rosanna Cardillo、Gianluca Nasini、Orso Vajna de Pava

  DOI：10.1016/s0031-9422(00)95105-7

  日期：1993.3

  structure of eucalyptene A, a fungal metabolite isolated from Clitocybe eucalyptorum , has been determined to be 4′-(2″,3″-butadienyloxy) trans -cinnamic acid methyl ester on the basis of 1 H and 13 C NMR evidence and chemical synthesis. Minor amounts of its cis isomer, eucalyptene B, were also isolated.

  摘要 Eucalyptene A 是一种从 Clitocybe eucalyptorum 中分离的真菌代谢物，根据 1 H 和 13 C NMR 证据确定其结构为 4′-(2″,3″-丁二烯氧基) 反式肉桂酸甲酯和化学合成。少量的顺式异构体桉树油 B 也被分离出来。