cis-2-(4-Methylbenzoyl)-6-oxabicyclo[3.2.1]octan-7-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cis-2-(4-Methylbenzoyl)-6-oxabicyclo[3.2.1]octan-7-one
• 英文别名: 2-(4-Methylbenzoyl)-6-oxa-bicyclo<3.2.1>octan-7-on；(1R,2S,5R)-2-(4-methylbenzoyl)-6-oxabicyclo[3.2.1]octan-7-one
• 化学式: C₁₅H₁₆O₃
• 分子量: 244.29
• InChiKey: PVAJZHBJEIDUFC-FRRDWIJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  cis-2-(4-Methylbenzoyl)-6-oxabicyclo[3.2.1]octan-7-one 在 一水合肼 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以71%的产率得到7t-hydroxy-4-p-tolyl-4ar,5,6,7,8,8ac-hexahydrophthalazin-1(2H)-one
  参考文献：
  名称：

  Preparation of Hydroxy-Substituted Hexahydrophthalazinones from Cyclohexane- and Norbornanelactones or Ketallactones

  摘要：

  Cyclohexane- and norbornanelactones (1, 5) as well as ketallactones (3, 7) and their hydrolytic products (2, 4a,b, 8) react with hydrazine hydrate to yield the hydroxy-substituted hexahydrophthalazinones 9-12. In the cyclizations, the configurations of the bridgehead atoms remain unaltered, and the hydroxy group retains its original position in the hydrazinolysis of 5 and 7. The compounds were characterized by IR, (1)H, and (13)C NMR spectroscopy.

  DOI：

  10.1007/s007060200001
• 作为产物：
  描述：

  甲苯 、 cis-1,2,3,6-tetrahydrophthalic anhydride 在 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 以55%的产率得到cis-2-(4-Methylbenzoyl)-6-oxabicyclo[3.2.1]octan-7-one
  参考文献：
  名称：

  Lactones and Ketal-Lactones Prepared from AlCl3-Catalyzed Reactions of Cycloalkenedicarboxylic Anhydrides with Toluene

  摘要：

  DOI：

  10.1055/s-1999-3578

文献信息

• Preparation and Structures of Isoindolone- or Pyrimidone-Condensed Heterocycles Containing a Hydroxy Group on a Cyclohexane or Norbornane Moiety
  作者：Ferenc Miklos、Pal Sohar、Antal Csampai、Reijo Sillanpaa、Geza Stajer

  DOI：10.2174/157017809787893136

  日期：2009.4.1

  With DL-valinol, 3-amino-1-propanol and o-aminothiophenol, aroyl(bi/tri)cyclic lactones 1 and 2 were cyclized to isoindole- 4-6, 8, 9, pyrimidinone- 10 or thiazepine- 7 condensed heterocycles. The ketal lactone 3 furnished the benzthiazoloisoindole 9 and mixtures of epimeric hydroxyphthalazinoquinazolinones 11 and 12. The structures were established by means of 1H and 13C NMR spectroscopy and in some cases by X-ray crystallography.

  在 DL-乙烯醇、3-氨基-1-丙醇和邻氨基苯硫酚的作用下，芳基（双/三）环内酯 1 和 2 环化成异吲哚-4-6、8、9、嘧啶酮-10 或硫氮杂环-7。酮内酯 3 生成了苯并噻唑基异吲哚 9 以及外延羟基酞嗪基喹唑啉酮 11 和 12 的混合物。这些化合物的结构是通过 1H 和 13C NMR 光谱以及某些情况下的 X 射线晶体学确定的。
• Radman; Hartung; Hoffmann, Pharmazie, 1995, vol. 50, # 6, p. 432 - 433
  作者：Radman、Hartung、Hoffmann、Strohl、Nuhn

  DOI：——

  日期：——
• Lactones and Ketal-Lactones Prepared from AlCl3-Catalyzed Reactions of Cycloalkenedicarboxylic Anhydrides with Toluene
  作者：József A. Szabó

  DOI：10.1055/s-1999-3578

  日期：1999.9
• Preparation of Hydroxy-Substituted Hexahydrophthalazinones from Cyclohexane- and Norbornanelactones or Ketallactones
  作者：József A. Szabó、Pál Sohár、Antal Csámpai、Géza Stájer

  DOI：10.1007/s007060200001

  日期：2002.3.1

  Cyclohexane- and norbornanelactones (1, 5) as well as ketallactones (3, 7) and their hydrolytic products (2, 4a,b, 8) react with hydrazine hydrate to yield the hydroxy-substituted hexahydrophthalazinones 9-12. In the cyclizations, the configurations of the bridgehead atoms remain unaltered, and the hydroxy group retains its original position in the hydrazinolysis of 5 and 7. The compounds were characterized by IR, (1)H, and (13)C NMR spectroscopy.