3-Ethoxy-3-methyl-2-nonanone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-Ethoxy-3-methyl-2-nonanone
• 英文别名: 3-Ethoxy-3-methylnonan-2-one
• 化学式: C₁₂H₂₄O₂
• 分子量: 200.321
• InChiKey: UMJBRMJUMSBGRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-甲基-1,2-壬二烯 在 tris(cetylpyridinium) 12-tungstophosphate 硫酸 、 双氧水 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 5.0h， 以20%的产率得到3-Ethoxy-3-methyl-2-nonanone
  参考文献：
  名称：

  Oxidation of Allenes and Alkynes with Hydrogen Peroxide Catalyzed by Cetylpyridinium Peroxotungstophosphate (PCWP)

  摘要：

  The oxidation of allenes and alkynes with hydrogen peroxide catalyzed by peroxotungstophosphate (PCWP) was examined. A variety of allenes were first converted into the corresponding alpha-ethoxy ketones upon treatment with 35% H2O2 under the influence of PCWP in a mixed solvent consisting of ethanol and dichloromethane. When the reaction was carried out using tert-butyl alcohol as a solvent, approximately a 1:1 regioisomeric mixture of alpha-hydroxy ketones was obtained along with a small amount of alpha-tert-butoxy ketone. Oxidation of internal alkynes such as 4-octyne by the PCWP-H2O2 system under phase-transfer conditions using chloroform produced alpha,beta-epoxy ketones in good yields. The same reaction in a mixed solvent of ethanol and chloroform gave alpha,beta-unsaturated ketones rather than alpha,beta-epoxy ketones. Plausible reaction paths are proposed for the oxidation of allenes and alkynes by the PCWP-H2O2 system.

  DOI：

  10.1021/jo00098a028

文献信息

• Oxidation of Allenes and Alkynes with Hydrogen Peroxide Catalyzed by Cetylpyridinium Peroxotungstophosphate (PCWP)
  作者：Satoshi Sakaguchi、Seiji Watase、Yuji Katayama、Yasuyuki Sakata、Yutaka Nishiyama、Yasutaka Ishii

  DOI：10.1021/jo00098a028

  日期：1994.9

  The oxidation of allenes and alkynes with hydrogen peroxide catalyzed by peroxotungstophosphate (PCWP) was examined. A variety of allenes were first converted into the corresponding alpha-ethoxy ketones upon treatment with 35% H2O2 under the influence of PCWP in a mixed solvent consisting of ethanol and dichloromethane. When the reaction was carried out using tert-butyl alcohol as a solvent, approximately a 1:1 regioisomeric mixture of alpha-hydroxy ketones was obtained along with a small amount of alpha-tert-butoxy ketone. Oxidation of internal alkynes such as 4-octyne by the PCWP-H2O2 system under phase-transfer conditions using chloroform produced alpha,beta-epoxy ketones in good yields. The same reaction in a mixed solvent of ethanol and chloroform gave alpha,beta-unsaturated ketones rather than alpha,beta-epoxy ketones. Plausible reaction paths are proposed for the oxidation of allenes and alkynes by the PCWP-H2O2 system.