8,8-二甲氧基-1,4-二氧杂螺[4.5]癸-6,9-二烯 | 75714-43-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 8,8-二甲氧基-1,4-二氧杂螺[4.5]癸-6,9-二烯
• 英文名称: Ethylene dimethyl bisketal of benzoquinone
• 英文别名: 8,8-Dimethoxy-1,4-dioxaspiro[4.5]deca-6,9-diene
• CAS: 75714-43-1
• 化学式: C₁₀H₁₄O₄
• 分子量: 198.219
• InChiKey: MTBFMHCHVSNUMJ-UHFFFAOYSA-N

物化性质

• 沸点：
  291.7±40.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8,8-二甲氧基-1,4-二氧杂螺[4.5]癸-6,9-二烯 在 溶剂黄146 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.5h， 以94%的产率得到1,4-二氧杂螺[4.5]癸-6,9-二烯-8-酮
  参考文献：
  名称：

  Anodic oxidation of mixed ethers of hydroquinones. A complementary route to benzoquinone monoketals

  摘要：

  DOI：

  10.1021/jo00314a040
• 作为产物：
  描述：

  甲醇 、 2-(4-甲氧基苯氧基)-1-乙醇 在 氢氧化钾 作用下， 生成 8,8-二甲氧基-1,4-二氧杂螺[4.5]癸-6,9-二烯
  参考文献：
  名称：

  An Efficient, Simple and Inexpensive Method for the Preparation of 1,4-Benzoquinone MonoketalsviaAnodic Oxidation of 1,4-Dimethoxybenzenes

  摘要：

  Anodic oxidation of a series of 1-substituted-2,5-dimethoxybenzenes gives 2-substituted-1,1,4,4-tetramethoxycyclohexa-2,5-dienes in almost quantitative crude yield. Selective monohydrolysis of these bis-ketals is possible in many cases, and gives 3-substituted-4,4-dimethoxycyclohexa-2,5-dienones in good to excellent overall yield.

  DOI：

  10.1080/00397919408010619

文献信息

• Thermal and photochemical rearrangements of cyclopropyl ethers of p-quinols. Competing reaction pathways leading to five- and six-membered ring spirocyclic ketones
  作者：Timothy N. Biggs、John S. Swenton

  DOI：10.1021/jo00047a006

  日期：1992.10

  Cyclopropyl ethers of p-quinols were prepared by reaction of 3"-methylenedispiro[1,3-dioxolone-2,1'-[2,5]-cyclohexadiene-4',1"(3"H)-isobenzofuran] and the associated ketone with ethyl diazoacetate/rhodium(II) acetate and diethylzinc/methylene iodide, respectively, and their thermal and photochemical rearrangements were studied. One major process at 180-200-degrees-C is cleavage of the carbon-oxygen bond at the spiro center of the quinol to give a phenoxy and cyclopropoxy radical pair. A cyclopropylcarbinyl-like opening of the latter radical followed by recombination of the ring-opened radical with the phenoxy radical resulted in formation of a six-membered ring spirocyclic ketone. The other major thermal process for the cyclopropyl ether is conveniently viewed as ring-opening of the cyclopropane ring without breakage of the quinol carbon-oxygen bond followed by a hydrogen shift to afford a functionalized vinyl ether. This compound reacts under the thermal conditions to afford as the final product the five-membered ring spirocyclic ketone. Interestingly, the importance of these two competing pathways is influenced by the stereochemistry of ester substituents on the cyclopropane ring. Two major processes have been established in the photochemistry of these cyclopropyl ethers of p-quinols. One is rearrangement to the same six-membered ring spirocyclic ketone as discussed above. The second process is photolysis to a styrene derivative and a carbene.
• Anodic oxidation of mixed ethers of hydroquinones. A complementary route to benzoquinone monoketals
  作者：Mark G. Dolson、John S. Swenton

  DOI：10.1021/jo00314a040

  日期：1981.1
• Biggs Timothy N., Swenton John S., J. Org. Chem., 57 (1992) N 21, S 5568- 5573
  作者：Biggs Timothy N., Swenton John S.

  DOI：——

  日期：——
• An Efficient, Simple and Inexpensive Method for the Preparation of 1,4-Benzoquinone Monoketals<i>via</i>Anodic Oxidation of 1,4-Dimethoxybenzenes
  作者：Elisabeth C. L. Gautier、Norman J. Lewis、Alexander McKillop、Richard J.K. Taylor

  DOI：10.1080/00397919408010619

  日期：1994.11

  Anodic oxidation of a series of 1-substituted-2,5-dimethoxybenzenes gives 2-substituted-1,1,4,4-tetramethoxycyclohexa-2,5-dienes in almost quantitative crude yield. Selective monohydrolysis of these bis-ketals is possible in many cases, and gives 3-substituted-4,4-dimethoxycyclohexa-2,5-dienones in good to excellent overall yield.