(2'S,3'S,4R,5S,6S)-2((E)-crotonyloxymethyl)-6-fluoro-4-O,5-O-(2',3'-dimethoxybutane-2',3'-diyl)-4,5-dihydroxycyclohex-2-en-1-one | 928618-26-2

• 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: (2'S,3'S,4R,5S,6S)-2((E)-crotonyloxymethyl)-6-fluoro-4-O,5-O-(2',3'-dimethoxybutane-2',3'-diyl)-4,5-dihydroxycyclohex-2-en-1-one
• 英文别名: [(2S,3S,4aS,5S,8aR)-5-fluoro-2,3-dimethoxy-2,3-dimethyl-6-oxo-5,8a-dihydro-4aH-1,4-benzodioxin-7-yl]methyl (E)-but-2-enoate
• CAS: 928618-26-2
• 化学式: C₁₇H₂₃FO₇
• 分子量: 358.364
• InChiKey: NNALZWUBEXBORX-OUNDHZOWSA-N

物化性质

• 沸点：
  434.5±45.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2'S,3'S,4R,5S,6S)-2((E)-crotonyloxymethyl)-6-fluoro-4-O,5-O-(2',3'-dimethoxybutane-2',3'-diyl)-4,5-dihydroxycyclohex-2-en-1-one 在 三氟乙酸 作用下， 反应 3.0h， 以95%的产率得到(4R,5S,6S)-(2(E)-crotonyloxymethyl)-6-fluoro-4,5-(dihydroxy)cyclohex-2-en-1-one
  参考文献：
  名称：

  Analogues of 2-crotonyloxymethyl-(4R,5R,6R)-4,5,6-trihydroxycyclohex-2-enone (COTC) with anti-tumor properties

  摘要：

  The syntheses of three novel analogues of the naturally occurring cytotoxic agent COTC are described and the results of bioassays of the target compounds against two lung cancer cell lines are presented. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2006.09.072
• 作为产物：
  描述：

  (2'S,3'S,4R,5S,6S)-6-fluoro-4-O,5-O-(2',3'-dimethoxybutane-2',3'-diyl)-4,5-dihydroxycyclohex-2-en-1-one 在 4-二甲氨基吡啶 吡啶 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 25.5h， 生成 (2'S,3'S,4R,5S,6S)-2((E)-crotonyloxymethyl)-6-fluoro-4-O,5-O-(2',3'-dimethoxybutane-2',3'-diyl)-4,5-dihydroxycyclohex-2-en-1-one
  参考文献：
  名称：

  Analogues of 2-crotonyloxymethyl-(4R,5R,6R)-4,5,6-trihydroxycyclohex-2-enone (COTC) with anti-tumor properties

  摘要：

  The syntheses of three novel analogues of the naturally occurring cytotoxic agent COTC are described and the results of bioassays of the target compounds against two lung cancer cell lines are presented. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2006.09.072

文献信息

• 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.
• Analogues of 2-crotonyloxymethyl-(4R,5R,6R)-4,5,6-trihydroxycyclohex-2-enone (COTC) with anti-tumor properties
  作者：Claire L. Arthurs、Natasha S. Wind、Roger C. Whitehead、Ian J. Stratford

  DOI：10.1016/j.bmcl.2006.09.072

  日期：2007.1

  The syntheses of three novel analogues of the naturally occurring cytotoxic agent COTC are described and the results of bioassays of the target compounds against two lung cancer cell lines are presented. (c) 2006 Published by Elsevier Ltd.