3,6-dibutyl-2,5-dihydroxy-1,4-benzoquinone | 68014-13-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,6-dibutyl-2,5-dihydroxy-1,4-benzoquinone
• 英文别名: 2,5-dibutyl-3,6-dihydroxy-[1,4]benzoquinone；2,5-Dibutyl-3,6-dihydroxy-[1,4]benzochinon；2,5-Dibutyl-3,6-dihydroxycyclohexa-2,5-diene-1,4-dione；2,5-dibutyl-3,6-dihydroxycyclohexa-2,5-diene-1,4-dione
• CAS: 68014-13-1
• 化学式: C₁₄H₂₀O₄
• 分子量: 252.31
• InChiKey: FORZYNKSFZMMJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,5-二羟基-1,4-苯喹酮 在 盐酸 、 正丁基锂 、 palladium 10% on activated carbon 、 氢气 、 4-甲基苯磺酸吡啶 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 正己烷 、 水 、 甲苯 为溶剂， -10.0~25.0 ℃ 、500.01 kPa 条件下， 反应 95.67h， 生成 3,6-dibutyl-2,5-dihydroxy-1,4-benzoquinone
  参考文献：
  名称：

  Design, synthesis, and SAR of embelin analogues as the inhibitors of PAI-1 (plasminogen activator inhibitor-1)

  摘要：

  The natural product embelin was found to have PAI-1 inhibitory activity with the IC50 value of 4.94 mu M. Based on the structure of embelin, a series of analogues were designed, synthesized, and evaluated for their ability to inhibit PAI-1. The SAR study on these compounds disclosed that the inhibitory potency largely depended on the hydroxyl groups at C2 and C5, and the length of the alkyl chains at C3 and C6. Compound 11 displayed the best PAI-1 inhibitory potency with the IC50 value of 0.18 mu M. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.03.045

文献信息

• Fichter, Justus Liebigs Annalen der Chemie, 1908, vol. 361, p. 391
  作者：Fichter

  DOI：——

  日期：——
• Reaction of organoboranes with 2,5-dihydroxy-1,4-benzoquinone and related compounds, and its application to the synthesis of rapanone
  作者：Kazuhiro Maruyama、Hiroyuki Saimoto、Yoshinori Yamamoto

  DOI：10.1021/jo00419a047

  日期：1978.12
• Asano et al., Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1955, vol. 75, p. 1568
  作者：Asano et al.

  DOI：——

  日期：——
• Design, synthesis, and SAR of embelin analogues as the inhibitors of PAI-1 (plasminogen activator inhibitor-1)
  作者：Fanglei Chen、Guiping Zhang、Zebin Hong、Zhonghui Lin、Min Lei、Mingdong Huang、Lihong Hu

  DOI：10.1016/j.bmcl.2014.03.045

  日期：2014.5

  The natural product embelin was found to have PAI-1 inhibitory activity with the IC50 value of 4.94 mu M. Based on the structure of embelin, a series of analogues were designed, synthesized, and evaluated for their ability to inhibit PAI-1. The SAR study on these compounds disclosed that the inhibitory potency largely depended on the hydroxyl groups at C2 and C5, and the length of the alkyl chains at C3 and C6. Compound 11 displayed the best PAI-1 inhibitory potency with the IC50 value of 0.18 mu M. (C) 2014 Elsevier Ltd. All rights reserved.