3,4-Dihydroxyspiro<5.5>undecan-3-en-4-one | 70990-65-7

• 分子结构分类: 有机化合物
• 英文名称: 3,4-Dihydroxyspiro<5.5>undecan-3-en-4-one
• 英文别名: 2,3-Dihydroxyspiro<5.5>undec-2-en-4-on；3,4-Dihydroxyspiro<5.5>undec-3-en-2-on；2,3-Dihydroxyspiro[5.5]undec-2-en-4-one
• CAS: 70990-65-7
• 化学式: C₁₁H₁₆O₃
• 分子量: 196.246
• InChiKey: DYPCQFDRZQTXQC-UHFFFAOYSA-N

物化性质

• 熔点：
  147 °C
• 沸点：
  352.7±42.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,4-Dihydroxyspiro<5.5>undecan-3-en-4-one 在 18-冠醚-6 、 碘甲烷 作用下， 以 甲苯 为溶剂， 反应 5.67h， 生成 2-羟基螺[4,5]-癸-1-烯-3-酮
  参考文献：
  名称：

  Reaction of Superoxide with Aci-Reductones

  摘要：

  Three reductones, 2,3-dihydroxy-4,4-diphenyl-2,5-cyclohexadien-1-one(11), 3,4-dihydroxycoumarin (35), and 3,4-dihydroxyspiro[5.5]undecan-3-en-4-one (64), were prepared and subsequently reacted with superoxide anion radical(O-2(.-)), generated from KO2 and 18-crown-6 polyether. The reactions were carried out in aprotic media and quenched with methyl iodide which facilitates the trapping of the various oxyanions formed. While a plethora of products were formed in each case [2-hydroxy-2-methyl-4,4-diphenyl-5-cyclohexene-1,3-dione (17), dimethyl 4,4-diphenylglutaconate (18), methyl 4,4-diphenyl-3-butenoate (19), phenylcinnamaldehyde (20), methyl 3-phenylcinnamate (21), and benzophenone (22) from 11; 3-hydroxy-2-methoxycoumarin (39), 2-carbomethoxy-2-hydroxy-3-coumaranone (40), 2-hydroxy-2-methyl-3-coumaranone (41), methyl o-hydroxyphenylglyoxylate (42), methyl salicylate (43), and catechol (44) from 35; and 2,4-dihydroxyspiro[5.5]undeca-1,4-dien-3-one (66), 2-hydroxyspiro[4.5]dec-1-en-3-one (70), dimethyl 1,1-cyclohexanediacetate (73), and dimethyl alpha-keto-1-[(methoxycarbonyl)methyl]cyclohexane (75) from 64], an overall analysis of the product distribution indicates that the basic elements of the reaction sequence are the same. The first step involves facile deprotonation and the concomitant generation of the reductone monoanion, a process which lends support to the suggestion of Afanas'ev and co-workers (Afanas'ev, I. B.; Grabovetskii, V. V.; Kuprianova, N. S. J. Chem. Sec. Perkin Trans. 2 1987, 281-285). Oxidation of this monoanion yields the corresponding triketone. Of the various options available to this polyketone, superoxide attack at the most electrophilic central carbonyl followed by oxidative cleavage and/or benzylic acid rearrangement are clearly the most prominent. These are followed by a variety of base catalyzed autoxidative processes which are highly dependent on the nature of the substrate.

  DOI：

  10.1021/jo00119a031
• 作为产物：
  描述：

  3,3-Bis(benzyloxycarbonyloxy)spiro<5.5>undecan-2,4-dion 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 以90%的产率得到3,4-Dihydroxyspiro<5.5>undecan-3-en-4-one
  参考文献：
  名称：

  Schank, Kurt; Blattner, Rudolf; Schmidt, Volker, Chemische Berichte, 1981, vol. 114, # 5, p. 1938 - 1950

  摘要：

  DOI：

文献信息

• Chemie freier cyclischer vicinaler Tricarbonyl-Verbindungen (‘1,2,3-Trione') Teil 2. Redox-Reaktionen von 1,2,3-Trionen mit En-1,2-diolen (‘Reduktonen'), 2-Alkoxy-en-1-olen, En-1,2-diaminen und verwandten Spezies Für Teil 1, s. [1].
  作者：Kurt Schank、Günter Bouillon、Michael Fünfrocken、Carlo Lick、Robert Lieder

  DOI：10.1002/1522-2675(200205)85:5<1295::aid-hlca1295>3.0.co;2-k

  日期：2002.5

  Chemistry of Free Cyclic Vicinal Tricarbonyl Compounds (‘1,2,3-Triones'). Part 2. Redox Reactions of 1,2,3-Triones with Ene-1,2-diols (‘Reductones'), 2-Alkoxy-en-1-ols, Ene-1,2-diamines, and Related Species. Midstanding carbonyl groups of cyclic 1,2,3-triones 4 possess outstanding electrophilic (electron-pair accepting) as well as oxidizing (one-electron accepting) properties. Their reactions with
• Schank, Kurt; Blattner, Rudolf; Bouillon, Guenter, Chemische Berichte, 1981, vol. 114, # 5, p. 1951 - 1957
  作者：Schank, Kurt、Blattner, Rudolf、Bouillon, Guenter

  DOI：——

  日期：——
• Schank, Kurt; Blattner, Rudolf, Chemische Berichte, 1981, vol. 114, # 5, p. 1958 - 1962
  作者：Schank, Kurt、Blattner, Rudolf

  DOI：——

  日期：——
• ALDER M.; SCHANK K.; SCHMIDT V., CHEM. BER., 1979, 112, NO 6, 2324-2331
  作者：ALDER M.、 SCHANK K.、 SCHMIDT V.

  DOI：——

  日期：——
• SCHANK K.; BLATTNER R.; BOUILLON G., CHEM. BER., 1981, 114, NO 5, 1951-1957
  作者：SCHANK K.、 BLATTNER R.、 BOUILLON G.

  DOI：——

  日期：——