甲基8-羟基-4,8-二甲基-6-氧代螺[2.5]辛-4-烯-5-羧酸酯 | 716381-20-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 甲基8-羟基-4,8-二甲基-6-氧代螺[2.5]辛-4-烯-5-羧酸酯
• 英文名称: Methyl 8-hydroxy-4,8-dimethyl-6-oxospiro[2.5]oct-4-ene-5-carboxylate
• CAS: 716381-20-3
• 化学式: C₁₂H₁₆O₄
• 分子量: 224.257
• InChiKey: NNSIQNWGGGXFBG-UHFFFAOYSA-N

物化性质

• 熔点：
  108-109 °C
• 沸点：
  371.6±42.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  甲基8-羟基-4,8-二甲基-6-氧代螺[2.5]辛-4-烯-5-羧酸酯 在 四氟化钛 作用下， 以 二氯甲烷 为溶剂， 以26%的产率得到Methyl 3-(2-fluoroethyl)-6-hydroxy-2,4-dimethylbenzoate
  参考文献：
  名称：

  Synthesis and reactivity of 1-hydroxyspiro[2.5]cyclooct-4-en-3-ones

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2004.03.134
• 作为产物：
  描述：

  1,1-乙酰基环丙烷 、 1,3-bis(trimethylsiloxy)-1-methoxybuta-1,3-diene 在 4 A molecular sieve 、 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以55%的产率得到甲基8-羟基-4,8-二甲基-6-氧代螺[2.5]辛-4-烯-5-羧酸酯
  参考文献：
  名称：

  Synthesis and reactivity of 1-hydroxyspiro[2.5]cyclooct-4-en-3-ones

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2004.03.134

文献信息

• [3+3] Cyclizations of 1,3-Bis(silyl enol ether)s with 1,1-Diacetylcyclopentane and 1,1-Diacetylcyclopropane
  作者：Peter Langer、Gopal Bose

  DOI：10.1002/anie.200351263

  日期：2003.9.5
• 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.
• [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 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.