(4R,5R,6S)-2-((E)-crotonyloxymethyl)-5,6-methanocyclohex-2-en-1-on-4-ol | 1024596-60-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (4R,5R,6S)-2-((E)-crotonyloxymethyl)-5,6-methanocyclohex-2-en-1-on-4-ol
• 英文别名: [(1S,5R,6R)-5-hydroxy-2-oxo-3-bicyclo[4.1.0]hept-3-enyl]methyl (E)-but-2-enoate
• CAS: 1024596-60-8
• 化学式: C₁₂H₁₄O₄
• 分子量: 222.241
• InChiKey: FMQVKGCMBJIOLQ-HSVGSZACSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (4S,5R,6S)-2-((E)-crotonyloxymethyl)-5,6-methano-4-O-(tert-butyldimethylsilyl)cyclohex-2-en-1-on-4-ol 在 三氟乙酸 作用下， 反应 1.0h， 以94%的产率得到(4R,5R,6S)-2-((E)-crotonyloxymethyl)-5,6-methanocyclohex-2-en-1-on-4-ol
  参考文献：
  名称：

  （-）-亚奎宁酸：用于合成具有抗肿瘤作用的2-巴豆酰氧基甲基-（4 R，5 R，6 R）-4,5,6-三羟基环己-2-烯酮（COTC）类似物的通用前体特性

  摘要：

  使用通用的手性池起始材料（-）-奎宁酸描述了链霉菌代谢产物COTC的三种新型类似物的合成。给出了针对两种肺癌细胞系A549和H460的目标化合物的生物测定结果。

  DOI：

  10.1016/j.tetlet.2008.02.059

文献信息

• (−)-Quinic acid: a versatile precursor for the synthesis of analogues of 2-crotonyloxymethyl-(4R,5R,6R)-4,5,6-trihydroxycyclohex-2-enone (COTC) which possess anti-tumour properties
  作者：Claire L. Arthurs、Katharine F. Lingley、Michela Piacenti、Ian J. Stratford、Tanja Tatic、Roger C. Whitehead、Natasha S. Wind

  DOI：10.1016/j.tetlet.2008.02.059

  日期：2008.4

  Syntheses of three novel analogues of the Streptomyces metabolite COTC are described, using the versatile chiral pool starting material, (−)-quinic acid. The results of bioassays of the target compounds against two lung cancer cell lines, A549 and H460, are presented.

  使用通用的手性池起始材料（-）-奎宁酸描述了链霉菌代谢产物COTC的三种新型类似物的合成。给出了针对两种肺癌细胞系A549和H460的目标化合物的生物测定结果。
• The synthesis of 2-oxyalkyl-cyclohex-2-enones, related to the bioactive natural products COTC and antheminone A, which possess anti-tumour properties
  作者：Claire L. Arthurs、Gareth A. Morris、Michela Piacenti、Robin G. Pritchard、Ian J. Stratford、Tanja Tatic、Roger C. Whitehead、Katharine F. Williams、Natasha S. Wind

  DOI：10.1016/j.tet.2010.08.072

  日期：2010.11

  The syntheses of five novel 2-oxyalkyl-cyclohex-2-enones, structurally related to the natural products COTC and antheminone A. are described. The target structures were selected in order to probe the influence of several key structural parameters on in vitro anti-cancer bioactivity. The results of a cytotoxicity bioassay of the compounds against non-small-cell lung cancer cell lines A549 and H460 are reported. The biological data provides useful information, which will help guide the future design of compounds in this class with enhanced anti-cancer activity. (C) 2010 Elsevier Ltd. All rights reserved.