spiro<5.5>undeca-7,10-diene-2,9-dione | 52727-32-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: spiro<5.5>undeca-7,10-diene-2,9-dione
• 英文别名: Spiro[5.5]undeca-1,4-diene-3,10-dione
• CAS: 52727-32-9
• 化学式: C₁₁H₁₂O₂
• 分子量: 176.215
• InChiKey: YOLRTFOLGFHLBG-UHFFFAOYSA-N

物化性质

• 熔点：
  98.5-102 °C
• 沸点：
  346.9±42.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  spiro<5.5>undeca-7,10-diene-2,9-dione 在 aluminum tri-tert-butoxide 作用下， 生成 9-hydroxyspiro<5.5>undeca-1,4-dien-3-one
  参考文献：
  名称：

  Iwata, Chuzo; Yamada, Minoru; Ida, Yasuo, Chemical and pharmaceutical bulletin, 1988, vol. 36, # 8, p. 2864 - 2871

  摘要：

  DOI：
• 作为产物：
  描述：

  (3-Oxospiro[5.5]undeca-1,4,10-trien-10-yl) 2,2,2-trifluoroacetate 在 水 作用下， 反应 0.03h， 以62%的产率得到spiro<5.5>undeca-7,10-diene-2,9-dione
  参考文献：
  名称：

  Rapid Formation of Hindered Cores Using an Oxidative Prins Process

  摘要：

  An unprecedented oxidative Prins transformation on phenol derivatives mediated by a hypervalent iodine reagent has been developed. This method allows a rapid access to highly substituted compact systems present in several natural products via a carbon-based addition on an aromatic core. Substitution at each ring position has been demonstrated, enabling synthesis of molecules with up to two contiguous quaternary carbon centers in good yield.

  DOI：

  10.1021/ol101851z

文献信息

• A modified procedure for the synthesis of spirodienones from phenolic .ALPHA.-diazoketones.
  作者：CHUZO IWATA、KAZUYUKI MIYASHITA、TOMOKO IMAO、KOJI MASUDA、NANA KONDO、SHUJI UCHIDA

  DOI：10.1248/cpb.33.853

  日期：——

  Rhodium (II) pivalate, rhodium (II) acetate, and palladium (II) acetate were found to be effective catalysts for the synthesis of spirodienones from phenolic α-diazoketones.

  新戊酸铑(II)、乙酸铑(II)和乙酸钯(II)被发现是从酚类α-重氮酮合成螺二烯酮的有效催化剂。
• Spiro-fused 2,5-cyclohexadienones from thermal 1,3-shifts in quinol vinyl ethers. Reactions in nonbenzenoid systems and limitations of the chemistry
  作者：John S. Swenton、David Bradin、Bradley D. Gates

  DOI：10.1021/jo00021a037

  日期：1991.10

  Addition of functionalized organolithium compounds to quinone monoketals furnished 4-hydroxy-2,5-cyclo-hexadienone derivatives. The 4-hydroxyl group of these molecules was then transformed into a vinyl ether, and the thermal [1,3]-shift chemistry of these functionalized vinyl ethers was studied. In dienone derivatives wherein a [3,3]-sigmatropic shift was not stereoelectronically possible, these molecules underwent thermal and photochemical [1,3]-oxygen-to-carbon migration, affording spiro-2,5-cyclohexadienones in good yield. However, for compounds in which the [3,3]-shift involving the vinyl ether was possible, this reaction occurred at or below room temperature. 1,5-Cyclooctadienebis(methyldiphenylphosphine)iridium hexafluorophosphate was found to be an especially efficient catalyst for the allyl-to-vinyl ether isomerization in these systems.
• IWATA, CHUZO;MIYASHITA, KAZUYUKI;IMAO, TOMOKO;MASUDA, KOJI;KONDO, NANA;UC+, CHEM. AND PHARM. BULL., 1985, 33, N 2, 853-855
  作者：IWATA, CHUZO、MIYASHITA, KAZUYUKI、IMAO, TOMOKO、MASUDA, KOJI、KONDO, NANA、UC+

  DOI：——

  日期：——
• IWATA, CHUZO;YAMADA, MINORU;IDA, YASUO;IMAO, TOMOKO;MIYAGAWA, HIROKO;MIYA+, CHEM. AND PHARM. BULL., 36,(1988) N 8, C. 2864-2871
  作者：IWATA, CHUZO、YAMADA, MINORU、IDA, YASUO、IMAO, TOMOKO、MIYAGAWA, HIROKO、MIYA+

  DOI：——

  日期：——