Riccardin A | 85318-25-8

• 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: Riccardin A
• 英文别名: 5-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-16,24-diol
• CAS: 85318-25-8
• 化学式: C₂₉H₂₆O₄
• 分子量: 438.523
• InChiKey: DXBKBLARMLPGND-UHFFFAOYSA-N

物化性质

• 沸点：
  645.1±55.0 °C(Predicted)
• 密度：
  1.212±0.06 g/cm3(Predicted)

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

• 作为反应物：
  描述：

  Riccardin A 在 manganese triacetate 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以38%的产率得到pusilatin E
  参考文献：
  名称：

  Isolation, Structure Elucidation, and Chemical Derivatization of a New Cyclic Bisbibenzyl Dimer, Pusilatin E, from the Liverwort Riccardia multifida subsp. decrescens

  摘要：

  A new cyclic bisbibenzyl dimer (1) has been isolated from the MeOH extract of the liverwort Riccardia multifida subsp. decrescens, together with two previously known bisbibenzyls [riccardin A (2) and marchantin I (3)] and a norneolignan [egonol 2-methylbutanoate (4)]. Extensive H-1- and C-13-NMR spectral measurements and chemical derivatization allowed the structure of dimeric riccardin A to be defined; it has been named pusilatin E (1).

  DOI：

  10.1021/np9605697
• 作为产物：
  描述：

  3-羟基-4-碘苯甲醛 在 bis(triphenylphosphine)nickel(II) chloride 、 锌 吡啶 、 氢气 、 sodium methylate 、 sodium 、 三溴化磷 、 potassium carbonate 、 三苯基膦 、 1,1,2,2-四苯乙烯 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 丙酮 、 苯 为溶剂， 反应 73.0h， 生成 Riccardin A
  参考文献：
  名称：

  Gottsegen, Agnes; Nogradi, Mihaly; Vermes, Borbala, Journal of the Chemical Society. Perkin transactions I, 1990, # 2, p. 315 - 320

  摘要：

  DOI：

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.
• Riccardin A and riccardin B, two novel cyclic bis(bibenzyls) possessing cytotoxicity from the liverwort Riccardia multifida (L.) S. Gray
  作者：Yoshinori Asakawa、Masao Toyota、Zenei Taira、Tsunematsu Takemoto、Masaru Kido

  DOI：10.1021/jo00161a009

  日期：1983.7
• GOTTSEGEN, AGNES;NOGRADI, MIHALY;VERMES, BORBALA;KAJTAR-PEREDY, MARIA;BIH+, J. CHEM. SOC. PERKIN TRANS. PT 1,(1990) N, C. 315-320
  作者：GOTTSEGEN, AGNES、NOGRADI, MIHALY、VERMES, BORBALA、KAJTAR-PEREDY, MARIA、BIH+

  DOI：——

  日期：——
• Gottsegen, Agnes; Nogradi, Mihaly; Vermes, Borbala, Journal of the Chemical Society. Perkin transactions I, 1990, # 2, p. 315 - 320
  作者：Gottsegen, Agnes、Nogradi, Mihaly、Vermes, Borbala、Kajtar-Peredy, Maria、Bihatsi-Karsai, Eva

  DOI：——

  日期：——
• Isolation, Structure Elucidation, and Chemical Derivatization of a New Cyclic Bisbibenzyl Dimer, Pusilatin E, from the Liverwort <i>Riccardia multifida</i> subsp. <i>decrescens</i>
  作者：Tatsuhiko Yoshida、Masao Toyota、Yoshinori Asakawa

  DOI：10.1021/np9605697

  日期：1997.2.1

  A new cyclic bisbibenzyl dimer (1) has been isolated from the MeOH extract of the liverwort Riccardia multifida subsp. decrescens, together with two previously known bisbibenzyls [riccardin A (2) and marchantin I (3)] and a norneolignan [egonol 2-methylbutanoate (4)]. Extensive H-1- and C-13-NMR spectral measurements and chemical derivatization allowed the structure of dimeric riccardin A to be defined; it has been named pusilatin E (1).