24-Methoxy-14-oxapentacyclo[20.2.2.210,13.115,19.02,7]nonacosa-1(24),2(7),3,5,10(29),11,13(28),15,17,19(27),22,25-dodecaene-5,16-diol | 1132675-16-1

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: 24-Methoxy-14-oxapentacyclo[20.2.2.210,13.115,19.02,7]nonacosa-1(24),2(7),3,5,10(29),11,13(28),15,17,19(27),22,25-dodecaene-5,16-diol
• CAS: 1132675-16-1
• 化学式: C₂₉H₂₆O₄
• 分子量: 438.523
• InChiKey: CIDCISRMIMBWEX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  33
• 可旋转键数：
  1
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,2,13,14-tetrahydro-9,17,22-trimethoxy-3,6:5,18-dietheno-8,12-metheno-12H-7-benzooxacycloeicosine 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以14%的产率得到Riccardin A
  参考文献：
  名称：

  Synthesis of riccardin C and its seven analogues. Part 1: The role of their phenolic hydroxy groups as LXRα agonists

  摘要：

  Riccardin C, a nuclear receptor LXR alpha selective agonist, is an 18-membered macrocyclic bisbibenzyl isolated from several liverworts. Synthesis of riccardin C and its seven O-methylated derivatives was accomplished. The synthetic sequence highlights an intramolecular Suzuki-Miyaura coupling in the formation of the 18-membered biaryl linkage present in riccardin C. The structure-activity relationship of these compounds suggests that all of the phenolic hydroxy groups present in riccardin C are essential for the activation of LXRa. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.12.022

文献信息

• Synthesis of riccardin C and its seven analogues. Part 1: The role of their phenolic hydroxy groups as LXRα agonists
  作者：Hideaki Hioki、Naoki Shima、Kota Kawaguchi、Kenich Harada、Miwa Kubo、Tomoyuki Esumi、Tomoko Nishimaki-Mogami、Jun-ichi Sawada、Toshihiro Hashimoto、Yoshinori Asakawa、Yoshiyasu Fukuyama

  DOI：10.1016/j.bmcl.2008.12.022

  日期：2009.2

  Riccardin C, a nuclear receptor LXR alpha selective agonist, is an 18-membered macrocyclic bisbibenzyl isolated from several liverworts. Synthesis of riccardin C and its seven O-methylated derivatives was accomplished. The synthetic sequence highlights an intramolecular Suzuki-Miyaura coupling in the formation of the 18-membered biaryl linkage present in riccardin C. The structure-activity relationship of these compounds suggests that all of the phenolic hydroxy groups present in riccardin C are essential for the activation of LXRa. (C) 2008 Elsevier Ltd. All rights reserved.