(3Z)-10-hydroxy-10-(5-hydroxy-3-methylpent-3-en-1-ynyl)-9(10H)-anthracenone | 263708-29-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (3Z)-10-hydroxy-10-(5-hydroxy-3-methylpent-3-en-1-ynyl)-9(10H)-anthracenone
• CAS: 263708-29-8
• 化学式: C₂₀H₁₆O₃
• 分子量: 304.345
• InChiKey: AZGXUDAPNYQHPK-KAMYIIQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.41
• 重原子数：
  23.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  57.53
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (3Z)-10-hydroxy-10-(5-hydroxy-3-methylpent-3-en-1-ynyl)-9(10H)-anthracenone 在 manganese(IV) oxide 作用下， 以 丙酮 为溶剂， 反应 1.0h， 以85%的产率得到(3Z)-10-hydroxy-10-(3-methyl-5-oxopent-3-en-1-ynyl)-9(10H)-anthracenone
  参考文献：
  名称：

  Anthracenone ABA analogue as a potential photoaffinity reagent for ABA-binding proteins

  摘要：

  An anthracenone analogue of abscisic acid (ABA) was synthesized as a potential photoaffinity reagent and tested for biological activity. Reaction between 10,10'-dimethoxy-9-anthrone with two equivalents of the lithiated dianion of cis-3-methylpent-2-en-4-yn-1-ol afforded an acetylenic alcohol key intermediate. Subsequent reduction of the triple bond, functional group manipulation of the side chain alcohol and deprotection of the dimethoxy protected anthrone provided anthracenone ABA analogue 7 as a potential photoaffinity reagent for ABA-binding proteins. The effect of natural ABA and the potential photoaffinity anthracenone ABA 7 on corn cell growth was determined at various concentrations. The results show that anthracenone ABA 7 is perceived as ABA-like, although producing less inhibition than ABA itself. For example, 7 at 33 mu M produces approximately the same inhibition as ABA at 10 mu M. Crown Copyright (C) 2000 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(99)00482-3
• 作为产物：
  描述：

  (Z)-3-甲基戊-2-烯-4-炔-1-醇 、 蒽醌 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 以56%的产率得到(3Z)-10-hydroxy-10-(5-hydroxy-3-methylpent-3-en-1-ynyl)-9(10H)-anthracenone
  参考文献：
  名称：

  Anthracenone ABA analogue as a potential photoaffinity reagent for ABA-binding proteins

  摘要：

  An anthracenone analogue of abscisic acid (ABA) was synthesized as a potential photoaffinity reagent and tested for biological activity. Reaction between 10,10'-dimethoxy-9-anthrone with two equivalents of the lithiated dianion of cis-3-methylpent-2-en-4-yn-1-ol afforded an acetylenic alcohol key intermediate. Subsequent reduction of the triple bond, functional group manipulation of the side chain alcohol and deprotection of the dimethoxy protected anthrone provided anthracenone ABA analogue 7 as a potential photoaffinity reagent for ABA-binding proteins. The effect of natural ABA and the potential photoaffinity anthracenone ABA 7 on corn cell growth was determined at various concentrations. The results show that anthracenone ABA 7 is perceived as ABA-like, although producing less inhibition than ABA itself. For example, 7 at 33 mu M produces approximately the same inhibition as ABA at 10 mu M. Crown Copyright (C) 2000 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(99)00482-3