螺[4.4]壬烷-1,4-二酮 | 39984-91-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 螺[4.4]壬烷-1,4-二酮
• 英文名称: Spiro<4.4>nonane-1,4-dione
• 英文别名: Spiro[4.4]nonane-1,4-dione
• CAS: 39984-91-3
• 化学式: C₉H₁₂O₂
• 分子量: 152.193
• InChiKey: KEVJXYMHFRHZMI-UHFFFAOYSA-N

物化性质

• 熔点：
  65-66.5 °C(Solv: hexane (110-54-3))
• 沸点：
  299.3±23.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 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：

  螺[4.4]壬烷-1,4-二酮 在 正丁基锂 、 溴 、 二异丙胺 作用下， 以 正己烷 、 溶剂黄146 、 苯 为溶剂， 反应 1.17h， 生成 spiro[14-oxatetracyclo[6.5.1.02,7.09,13]tetradeca-2,4,6-triene-11,1'-cyclopentane]-10,12-dione
  参考文献：
  名称：

  Sudini; Khire; Pandey, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2000, vol. 39, # 10, p. 738 - 745

  摘要：

  DOI：
• 作为产物：
  描述：

  环戊酮 在 三氟化硼乙醚 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 苯 为溶剂， 生成 螺[4.4]壬烷-1,4-二酮
  参考文献：
  名称：

  Sudini; Khire; Pandey, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2000, vol. 39, # 10, p. 738 - 745

  摘要：

  DOI：

文献信息

• Efficient photochemical transformation of spiro[4.n]-2,5-diones to γ-alkylidene γ-butyrolactones: its relevance to photostability of Fredericamycin A
  作者：Bipin Pandey、Ravinder S. Reddy、Pradeep Kumar

  DOI：10.1039/c39930000870

  日期：——

  Irradiation of a variety of model spirodiones related to the antitumour antibiotic Fredericamycin A in various solvents at 300 nm furnishes quantitative yields of γ-alkylidene γ-butyrolactones; its relevance to the typical shape alteration, photostability and consequent biological response of Fredericamycin is discussed.

  在 300 nm 的各种溶剂中照射与抗肿瘤抗生素 Fredericamycin A 相关的各种模型螺环酮，可提供 γ-亚烷基 γ-丁内酯的定量产率；讨论了它与 Fredericamycin 的典型形状改变、光稳定性和随后的生物反应的相关性。
• Formation of 2,2-disubstituted 1,3-cyclopentanediones from ketals with 1,2-bis(trimethylsilyloxy)cyclobutene
  作者：Yong-Jin Wu、Dean W. Strickland、Tracy J. Jenkins、Pei-Ying Liu、D. Jean Burnell

  DOI：10.1139/v93-169

  日期：1993.9.1

  The direct formation of 2,2-disubstituted 1,3-cyclopentanedione compounds by a Lewis acid catalysed reaction with 1,2-bis(trimethylsilyloxy)cyclobutene proceeds in good to excellent yields with unhindered ketals, but steric hindrance reduces the yields considerably. A carbonyl group α or β to the ketal, or a carbon–carbon double bond α to the ketal, stops the reaction completely. Orthoesters do not give geminally acylated products in synthetically useful yields.

  通过路易斯酸催化的反应，使用1,2-双(三甲基硅氧基)环丁烯与没有受阻碍的缩酮，直接形成2,2-二取代的1,3-环戊二酮化合物，产率良好至优秀，但立体位阻显著降低了产率。位于缩酮α或β位置的羰基，或者与缩酮α位置相邻的碳-碳双键会完全停止反应。正酯不会以合成有用的产率产生双酰化产物。
• Model studies aimed at the synthesis of Fredericamycin A. A simple o-quinodimethane route to the spiro naphthalene portion
  作者：Robert D. Bach、Russell C. Klix

  DOI：10.1016/s0040-4039(00)84427-5

  日期：1986.1

  The three contiguous rings in the naphthalene portion of a model compound related to Fredericamycin A have been prepared by the Diels-Alder cycloaddition reaction of an α-bromo-o-quinodimethane intermediate to the carbon—carbon double bond of the spiro dienophile, spiro[4.4]non-2, 3-ene-1, 4-dione.

  模型化合物的萘部分中与弗雷德里卡霉素A相关的三个连续环是通过α-溴-邻-喹二甲烷中间体与螺双亲二烯体spiro []的碳-碳双键的Diels-Alder环加成反应制备的。 4.4]非2、3-烯-1、4-二酮。
• Lewis Acid Catalyzed Geminal Acylation Reaction of Ketones with 1,2-Bis[(trimethylsilyl)oxy]cyclobutene: Direct Formation of 2,2-Disubstituted 1,3-Cyclopentanediones
  作者：Tracy J. Jenkins、D. Jean Burnell

  DOI：10.1021/jo00085a041

  日期：1994.3

  Ketones reacted with 1,2-bis((trimethylsilyl)oxy)cyclobutene (1) under catalysis by boron trifluoride etherate to yield 2,2-disubstituted 1,3-cyclopentanedione products via silylated cyclobutanone intermediates in a two-step, one-pot process. In many instances addition of a small amount of water to the reaction medium after completion of the first step assisted the subsequent rearrangement to the product, such that reversion of the intermediate to the starting ketone became an insignificant process. Yields were best with cyclohexanones (>90%), but steric hindrance and conjugated double bonds reduced yields considerably.
• Kobayashi, Yoshiro; Taguchi, Takeo; Morikawa, Tsutomu, Chemical and pharmaceutical bulletin, 1980, vol. 28, # 1, p. 262 - 267
  作者：Kobayashi, Yoshiro、Taguchi, Takeo、Morikawa, Tsutomu、Tokuno, Etsuko、Sekiguchi, Shoh

  DOI：——

  日期：——