ethyl 4,11-dihydroxy-2-methyl-5,10-dioxoanthra[2,3-b]furan-3-carboxylate | 84914-96-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: ethyl 4,11-dihydroxy-2-methyl-5,10-dioxoanthra[2,3-b]furan-3-carboxylate
• 英文别名: ethyl 4,11-dihydroxy-2-methyl-5,10-dioxo-5,10-dihydroanthra[2,3-b]furan-3-carboxylate；ethyl 4,11-dihydroxy-2-methyl-5,10-dioxonaphtho[2,3-f][1]benzofuran-3-carboxylate
• CAS: 84914-96-5
• 化学式: C₂₀H₁₄O₇
• 分子量: 366.327
• InChiKey: DZBXNQCXDAXQML-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  114
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 4,11-dihydroxy-2-methyl-5,10-dioxoanthra[2,3-b]furan-3-carboxylate 在 硫酸 作用下， 反应 5.0h， 以82%的产率得到4,11-dihydroxy-2-methyl-5,10-dioxo-5,10-dihydroanthra[2,3-b]furan-3-carboxylic acid
  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：
• 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 5.5h， 生成 ethyl 4,11-dihydroxy-2-methyl-5,10-dioxoanthra[2,3-b]furan-3-carboxylate
  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

• Synthesis and fluorescence of anthra[2,3-b]furan-5,10-dione derivatives
  作者：A. E. Shchekotikhin、E. K. Shevtsova、V. F. Traven’

  DOI：10.1134/s1070428007110164

  日期：2007.11

  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).
• 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.
• Synthesis and photochemical properties of phenoxy derivatives of anthra[2,3-b]furan-5,10-dione
  作者：A. E. Shchekotikhin、E. K. Shevtsova、Yu. N. Luzikov、V. A. Barachevskii、V. F. Traven’

  DOI：10.1134/s1070428008060134

  日期：2008.6

  Nucleophilic replacement of the hydroxy groups in ethyl 4,11-dihydroxy-2-methyl-5,10-dioxo-5,10-dihydroanthra[2,3-b]furan-3-carboxylate by chlorine upon treatment with phosphorus acid chlorides gave the corresponding 4(11)-chloro derivatives which were converted into photochromic ethyl 4(11)-phenoxy-2-methyl-5,10-dioxo-5,10-dihydroanthra[2,3-b]furan-3-carboxylates. Photoinduced decomposition of the latter leads to the formation of phenol and fluorescent hydroxyanthra[2,3-b]furandiones.
• 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：——
• Gorelik, M. V.; Mishina, E. V., Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, # 10, p. 1900 - 1904
  作者：Gorelik, M. V.、Mishina, E. V.

  DOI：——

  日期：——