3-acetyl-4,11-dihydroxy-2-methylanthra[2,3-b]furan-5,10-dione | 84914-94-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 3-acetyl-4,11-dihydroxy-2-methylanthra[2,3-b]furan-5,10-dione
• 英文别名: 3-acetyl-4,11-dihydroxy-2-methylnaphtho[2,3-f][1]benzofuran-5,10-dione
• CAS: 84914-94-3
• 化学式: C₁₉H₁₂O₆
• 分子量: 336.301
• InChiKey: QWUWIJQKKCGTLN-UHFFFAOYSA-N

物化性质

• 熔点：
  243-246 °C
• 沸点：
  443.1±40.0 °C(Predicted)
• 密度：
  1.524±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.13
• 重原子数：
  25.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  104.81
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1-碘代丙烷 、 3-acetyl-4,11-dihydroxy-2-methylanthra[2,3-b]furan-5,10-dione 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以61%的产率得到3-acetyl-2-methyl-4,11-dipropoxyanthra[2,3-b]furan-5,10-dione
  参考文献：
  名称：

  Synthesis and fluorescence of anthra[2,3-b]furan-5,10-dione derivatives

  摘要：

  4,11-Dialkoxyanthra[2,3-b]furan-5,10-diones containing various substituents in the 3-position were synthesized. Reactions of these compounds with primary and secondary amines resulted in nucleophilic replacement of one or two alkoxy groups by the corresponding amine residues. 4,11-Dialkoxy derivatives of anthra[2,3-b]furan-5,10-dione showed fluorescence with large Stokes shifts (170-200 nm).

  DOI：

  10.1134/s1070428007110164
• 作为产物：
  描述：

  1,4-二羟基蒽醌 在 盐酸 、 manganese(IV) oxide 、 potassium carbonate 作用下， 以 溶剂黄146 、 二甲基亚砜 为溶剂， 反应 4.25h， 生成 3-acetyl-4,11-dihydroxy-2-methylanthra[2,3-b]furan-5,10-dione
  参考文献：
  名称：

  Gorelik, M. V.; Mishina, E. V., Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, # 10, p. 1900 - 1904

  摘要：

  DOI：

文献信息

• Insecticidal heterolignans—Tubuline polymerization inhibitors with activity against chewing pests
  作者：Jens Frackenpohl、Isabelle Adelt、Horst Antonicek、Christian Arnold、Patricia Behrmann、Nicole Blaha、Jutta Böhmer、Oliver Gutbrod、Roman Hanke、Sabine Hohmann、Marc van Houtdreve、Peter Lösel、Olga Malsam、Martin Melchers、Valentina Neufert、Elisabeth Peschel、Udo Reckmann、Thomas Schenke、Hans-Peter Thiesen、Robert Velten、Kathrin Vogelsang、Hans-Christoph Weiss

  DOI：10.1016/j.bmc.2009.01.042

  日期：2009.6

  Starting from natural product podophyllotoxin 1 substituted heterolignans were identified with promising insecticidal in vivo activity. The impact of substitution in each segment of the core structure was investigated in a detailed SAR study, and variation of substituents in both aromatic moieties afforded derivatives 5 and 43 with broad insecticidal activity against lepidopteran and coleopteran species. In vitro measurements supported by modeling studies indicate that heterolignans 3-134 act as tubuline polymerization inhibitors interacting with the colchicine-binding site. Insect specific structure-activity effects were observed showing that the insecticidal SAR described herein differs from reported cytotoxicity studies. (C) 2009 Elsevier Ltd. All rights reserved.
• GORELIK, M. V.;MISHINA, E. V., ZH. ORGAN. XIMII, 1983, 19, N 10, 2185-2190
  作者：GORELIK, M. V.、MISHINA, E. V.

  DOI：——

  日期：——