1,2-cyclononanedione | 3008-36-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2-cyclononanedione
• 英文别名: Cyclononanedione；cyclononane-1,2-dione
• CAS: 3008-36-4
• 化学式: C₉H₁₄O₂
• 分子量: 154.209
• InChiKey: PBXBFQQMHCIRKP-UHFFFAOYSA-N

物化性质

• 沸点：
  80-82 °C(Press: 3 Torr)
• 密度：
  1.010±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• 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：

  1,2-cyclononanedione 在 三氟化硼乙醚 、 sodium amide 、 叔丁醇 作用下， 以 二氯甲烷 为溶剂， 反应 5.5h， 生成 C₁₇H₂₂O₃
  参考文献：
  名称：

  Arynic condensation of ketone enolates. 17. New general access to benzocyclobutene derivatives

  摘要：

  DOI：

  10.1021/jo00359a008
• 作为产物：
  描述：

  2,5-hexamethylene-1,4-dioxaspiro<2.2>pentane 在 4 A molecular sieve silica gel 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.5h， 生成 1,2-cyclononanedione
  参考文献：
  名称：

  1,4-Dioxaspiro[2.2]pentanes. Synthesis, spectroscopic properties, and reactions with nucleophiles

  摘要：

  A number of simple allenes have been converted cleanly to the corresponding 1,4-dioxaspiro[2.2]pentanes in good yields by oxidation with dimethyldioxirane. Mono- and trisubstituted allenes give the anti diastereomers with good stereoselectivity, whereas 1,3-disubstituted allenes show only a slight preference for the anti,anti isomers, unless steric effects are extreme. Stereochemical assignments are based on steric considerations and a consistent set of NMR characteristics that permit structural attributions. The addition of a range of nucleophiles (water, alcohols, amines, thiophenol, acetate, chloride, and fluoride) to these intermediates proceeded smoothly under buffered conditions to give highly functionalized products of general type 5. These reactions were shown to take place with the appropriate selectivities for S(N)2 substitutions in instances where these features were observable, namely, regioselective attack at the less-substituted epoxide carbon and inversion of configuration at the site of substitution. Under acidic conditions dioxaspiropentanes gave mixtures of other types of products, which appear to arise from carbocationic processes.

  DOI：

  10.1021/jo00003a044

文献信息

• A very efficient preparation of 1,2-diketones
  作者：M.C. Carre、P. Caubere

  DOI：10.1016/s0040-4039(00)98629-5

  日期：1985.1

  Treatment of α-thiomethylketones with CuCl2-CuO in aqueous acetone affords the corresponding 1,2-dicarbonyl compounds.

  在丙酮水溶液中用CuCl 2 -CuO处理α-硫代甲基酮，得到相应的1，2-二羰基化合物。
• Study on the Synthesis of 1,2-diketones
  作者：Peng Liu、Yu-Mei Zhang、Hong-Li Zhang

  DOI：10.1080/15533171003766600

  日期：2010.5.11

  method is discussed for preparation of 1,2-diketones: Esters 1 was used as starting material, the intermediate enol 2 was obtained from sodium and trimethylsilyl chloride via acyloin condensation reaction, while bromine water was used in the further experiment as the oxidation reagent to oxidize compound 2 in the mixed solvent THF/H 2 O. Four kinds of 1,2-diketones have been synthesized in the new way

  讨论了制备1,2-二酮的新方法：以酯1为起始原料，通过酰氯缩合反应从钠和三甲基甲硅烷基氯中制得中间体烯醇2，而在进一步的实验中使用溴水进行氧化。在混合溶剂THF / H 2 O中氧化化合物2的化学试剂。以这种新方式合成了四种1,2-二酮，一种是直链化合物3a，3b，另一种是环化合物3c，3d。通过IR和1 HNMR确认目标化合物。
• Many-Membered Carbon Rings. VI. Unsaturated Nine-membered Cyclic Hydrocarbons¹
  作者：A. T. Blomquist、Liang Huang Liu、James C. Bohrer

  DOI：10.1021/ja01134a052

  日期：1952.7
• 368. Physical properties and chemical constitution. Part XL. The electrical dipole moments of some cyclic diketones
  作者：C. W. N. Cumper、G. B. Leton、A. I. Vogel

  DOI：10.1039/jr9650002067

  日期：——
• Zur Kenntnis des Kohlenstoffringes. Ein Herstellungsverfahren für vielgliedrige Cyclanone
  作者：V. Prelog、L. Frenkiel、Magrit Kobelt、P. Barman

  DOI：10.1002/hlca.19470300637

  日期：1947.10.15