isopropyl 8-hydroxy-4,8-dimethyl-6-oxospiro[2.5]oct-4-ene-5-carboxylate | 716381-22-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: isopropyl 8-hydroxy-4,8-dimethyl-6-oxospiro[2.5]oct-4-ene-5-carboxylate
• 英文别名: Propan-2-yl 8-hydroxy-4,8-dimethyl-6-oxospiro[2.5]oct-4-ene-5-carboxylate
• CAS: 716381-22-5
• 化学式: C₁₄H₂₀O₄
• 分子量: 252.31
• InChiKey: PWPUJHIKSUVXHR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  isopropyl 8-hydroxy-4,8-dimethyl-6-oxospiro[2.5]oct-4-ene-5-carboxylate 在 4 A molecular sieve 、 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 以53%的产率得到isopropyl 3-(2-chloroethyl)-6-hydroxy-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：

  乙酰乙酸异丙酯 、 1,1-乙酰基环丙烷 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 以68%的产率得到isopropyl 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

• Domino “[3+3]-Cyclization-Homo-Michael” Reactions of 1,3-Bissilyl Enol Ethers with 1,1-Diacylcyclopropanes
  作者：Gopal Bose、Van Thi Hong Nguyen、Ehsan Ullah、Sunanda Lahiri、Helmar Görls、Peter Langer

  DOI：10.1021/jo0485278

  日期：2004.12.1

  The Lewis acid mediated domino " [3+3] -cyclization-homo-Michael" reaction of 1,3-bissilyl enol ethers with 1,1-diacylcyclopropanes allows an efficient one-pot synthesis of functionalized salicylates containing a halogenated side chain. A great variety of substitution patterns could be realized by variation of the starting materials and of the Lewis acid. The mechanism of the domino process was studied.
• 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.