1,8,8-trimethyl-3-oxa-bicyclo[3.2.1]octan-2-one | 507-96-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 1,8,8-trimethyl-3-oxa-bicyclo[3.2.1]octan-2-one
• 英文别名: α-Campholide；α-Campholid；1,8,8-Trimethyl-3-oxabicyclo[3.2.1]octan-2-one
• CAS: 507-96-0
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: RRAKNOYKYSYKGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,8,8-trimethyl-3-oxa-bicyclo[3.2.1]octan-2-one 、 alkaline earth salt of/the/ methylsulfuric acid 生成 2,2-二甲基-环戊烷-1,1,3-三羧酸
  参考文献：
  名称：

  Baeyer; Villiger, Chemische Berichte, 1899, vol. 32, p. 3628

  摘要：

  DOI：
• 作为产物：
  描述：

  樟脑 在 Petroleum ether 作用下， 生成 1,8,8-trimethyl-3-oxa-bicyclo[3.2.1]octan-2-one
  参考文献：
  名称：

  Baeyer; Villiger, Chemische Berichte, 1899, vol. 32, p. 3628

  摘要：

  DOI：

文献信息

• Baeyer-Villiger Oxidation and Oxidative Cascade Reactions with Aqueous Hydrogen Peroxide Catalyzed by Lipophilic Li[B(C6F5)4] and Ca[B(C6F5)4]2
  作者：Muhammet Uyanik、Daisuke Nakashima、Kazuaki Ishihara

  DOI：10.1002/anie.201204286

  日期：2012.9.3

  Efficient and selective: Two lipophilic catalysts were used for Baeyer–Villiger (BV) oxidations to give lactones in high yields (see scheme). Cascade reactions involving this BV oxidation were used to selectively obtain either unsaturated carboxylic acids or hydroxylactones in high yields from β‐silyl cyclohexanones.

  高效和选择性：两种亲脂性催化剂用于Baeyer-Villiger（BV）氧化，以高收率得到内酯（请参阅方案）。涉及这种BV氧化的级联反应用于从β-甲硅烷基环己酮中高收率选择性地获得不饱和羧酸或羟基内酯。
• One-step annulation. A convenient method for the preparation of diols, spirolactones, and spiroethers from lactones
  作者：Persephone Canonne、Georges B. Foscolos、Denis Belanger

  DOI：10.1021/jo01298a016

  日期：1980.5
• Phase transfer catalyzed oxidation of ketones with borax-H2O2
  作者：C. S. Pande、N. Gupta

  DOI：10.1007/bf00807154

  日期：——

  Borax forms peroxy species when dissolved in 30% hydrogen peroxide which can be transferred into the organic phase when biphase mixtures are agitated. The addition of a catalytic amount of BTEAC promotes the transfer. This biphase system was used for the Baeyer-Villiger oxidation of several ketones insoluble in water. Effects of changing various parameters, e.g. temperature, time, amount of H2O2 etc. were investigated. At higher temperature (ca 80 degrees C), 100% conversion could be achieved in 2-4 h. The results show that under appropriate conditions this reaction is of synthetic value for the oxidation of acid-sensitive ketones using inexpensive and easily available reagents.
• Rupe; Jaeggi, Helvetica Chimica Acta, 1920, vol. 3, p. 655
  作者：Rupe、Jaeggi

  DOI：——

  日期：——
• Tafel; Bublitz, Chemische Berichte, 1905, vol. 38, p. 3808
  作者：Tafel、Bublitz

  DOI：——

  日期：——

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