Ethyl 8-hydroxy-4,8-dimethyl-6-oxospiro[2.5]oct-4-ene-5-carboxylate | 716381-23-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Ethyl 8-hydroxy-4,8-dimethyl-6-oxospiro[2.5]oct-4-ene-5-carboxylate
• CAS: 716381-23-6
• 化学式: C₁₃H₁₈O₄
• 分子量: 238.284
• InChiKey: GCQDRTZOFJLWAV-UHFFFAOYSA-N

物化性质

• 熔点：
  56-57 °C
• 沸点：
  383.5±42.0 °C(predicted)
• 密度：
  1.20±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Ethyl 8-hydroxy-4,8-dimethyl-6-oxospiro[2.5]oct-4-ene-5-carboxylate 在 硫酸 作用下， 以 丙酮 为溶剂， 以39%的产率得到ethyl 6-hydroxy-3-(2-hydroxyethyl)-2,4-dimethylbenzoate
  参考文献：
  名称：

  Synthesis, reactions and structure–activity relationships of 1-hydroxyspiro[2.5]cyclooct-4-en-3-ones: Illudin analogs with in vitro cytotoxic activity

  摘要：

  1-Hydroxyspiro [2.5]cyclooet-4-en-3-ones-analogs of natural illudines-were prepared in good yields by cyclization of 1,3-dicarbonyl dianions or 1,3-bis-silyl enol ethers ('masked dianions') with 1,1-diacylcyclopropanes. Several spirocyclopropanes showed a significant antiproliferative activity against human leukemia HL60 cells in vitro. 1-Hydroxyspiro [2.5]cyclooct-4-en-3-ones represent highly reactive precursors of unstable spiro[5.2]cycloocta-4,7-dien-6-ones and reactions with a number of nucleophiles were studied. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.03.037
• 作为产物：
  描述：

  1,1-乙酰基环丙烷 、 1-ethoxy-1,3-bis(trimethylsilyloxy)buta-1,3-diene 在 4 A molecular sieve 、 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 以48%的产率得到Ethyl 8-hydroxy-4,8-dimethyl-6-oxospiro[2.5]oct-4-ene-5-carboxylate
  参考文献：
  名称：

  Synthesis, reactions and structure–activity relationships of 1-hydroxyspiro[2.5]cyclooct-4-en-3-ones: Illudin analogs with in vitro cytotoxic activity

  摘要：

  1-Hydroxyspiro [2.5]cyclooet-4-en-3-ones-analogs of natural illudines-were prepared in good yields by cyclization of 1,3-dicarbonyl dianions or 1,3-bis-silyl enol ethers ('masked dianions') with 1,1-diacylcyclopropanes. Several spirocyclopropanes showed a significant antiproliferative activity against human leukemia HL60 cells in vitro. 1-Hydroxyspiro [2.5]cyclooct-4-en-3-ones represent highly reactive precursors of unstable spiro[5.2]cycloocta-4,7-dien-6-ones and reactions with a number of nucleophiles were studied. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.03.037

文献信息

• Synthesis and reactivity of 1-hydroxyspiro[2.5]cyclooct-4-en-3-ones
  作者：Gopal Bose、Peter Langer

  DOI：10.1016/j.tetlet.2004.03.134

  日期：2004.5

  The first 1-hydroxyspiro[2.5]cyclooct-4-en-3-ones were prepared by cyclization of free and masked 1,3-dicarbonyl dia-nions with 1,1-diacetylcyclopropane. 1-Hydroxyspiro[2.5]cyclooct-4-en-3-ones represent precursors of unstable spiro[5.2]cycloocta-4,7-dien-6-ones and reactions with a number of nucleophiles were studied. The reactions are enhanced by dynamic spiro-activation. (C) 2004 Elsevier Ltd. All rights reserved.
• [DE] LEITSTRUKTUREN FÜR ZYTOSTATISCHE VERBINDUNGEN AUF BASIS VON SPIROVERBINDUNGEN<br/>[EN] LEAD STRUCTURES FOR CYTOSTATIC COMPOUNDS BASED ON SPIRO COMPOUNDS<br/>[FR] MATRICES DESTINEES A DES COMPOSES CYTOSTATIQUES A BASE DE COMPOSES SPIRO
  申请人：UNIV ERNST MORITZ ARNDT

  公开号：WO2007051622A1

  公开（公告）日：2007-05-10

  [EN] The invention relates to lead structures of general formula X for the treatment of tumor diseases. The invention further relates to pharmaceutical compositions containing said compounds as well as the use of said compounds for treating diseases.
  [FR] L'invention concerne des matrices représentées par la formule générale X, destinées à la thérapie de maladies tumorales. L'invention concerne également des compositions pharmaceutiques contenant ces composés et l'utilisation de ces composés dans le traitement de maladies.
  [DE] Die vorliegende Erfindung Leitstrukturen der altgemeinen Formel X für die Therapie von Tumorerkrankungen. Die Erfindung betrifft weiterhin pharmazeutische Zusammensetzungen, die diese Verbindungen enthalten und die Verwendung dieser Verbindungen bei der Behandlung von Erkrankungen.
• Synthesis, reactions and structure–activity relationships of 1-hydroxyspiro[2.5]cyclooct-4-en-3-ones: Illudin analogs with in vitro cytotoxic activity
  作者：Gopal Bose、Karin Bracht、Patrick J. Bednarski、Michael Lalk、Peter Langer

  DOI：10.1016/j.bmc.2006.03.037

  日期：2006.7.15

  1-Hydroxyspiro [2.5]cyclooet-4-en-3-ones-analogs of natural illudines-were prepared in good yields by cyclization of 1,3-dicarbonyl dianions or 1,3-bis-silyl enol ethers ('masked dianions') with 1,1-diacylcyclopropanes. Several spirocyclopropanes showed a significant antiproliferative activity against human leukemia HL60 cells in vitro. 1-Hydroxyspiro [2.5]cyclooct-4-en-3-ones represent highly reactive precursors of unstable spiro[5.2]cycloocta-4,7-dien-6-ones and reactions with a number of nucleophiles were studied. (c) 2006 Elsevier Ltd. All rights reserved.