3-acetoxy-2-undecanone | 100545-43-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3-acetoxy-2-undecanone
• 英文别名: 2-oxoundecan-3-yl acetate；3-acetoxy-undecan-2-one
• CAS: 100545-43-5
• 化学式: C₁₃H₂₄O₃
• 分子量: 228.332
• InChiKey: ZKEOZHMEAKHYRV-UHFFFAOYSA-N

物化性质

• 沸点：
  124 °C(Press: 4 Torr)
• 密度：
  0.931 g/cm3(Temp: 25 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  16
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 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：

  3-acetoxy-2-undecanone 生成 十一碳-3-烯-2-酮
  参考文献：
  名称：

  Colonge,J.; Dubin,J.-C., Bulletin de la Societe Chimique de France, 1960, p. 1180 - 1186

  摘要：

  DOI：
• 作为产物：
  描述：

  2-十一酮 在 硫酸 、 溴 、 potassium carbonate 作用下， 以 乙醚 为溶剂， 生成 3-acetoxy-2-undecanone
  参考文献：
  名称：

  Colonge,J.; Dubin,J.-C., Bulletin de la Societe Chimique de France, 1960, p. 1180 - 1186

  摘要：

  DOI：

文献信息

• [EN] PHEROMONES<br/>[FR] PHEROMONES
  申请人：EAST MALLING RES LTD

  公开号：WO2006000798A1

  公开（公告）日：2006-01-05

  The apple leaf midge and raspberry cane midge pheromones have been found to be acetoxyheptadecenone and acetoxyundecanone, respectively, and uses for the related C_9-19 oxoalkyl or oxoalkenyl molecules substituted with a lower alkanoyloxy group are provided, including monitoring population levels of the midge and control of midge populations by disrupting mating patterns.

  苹果叶小蚜和覆盆子藤小蚜的信息素分别被发现为乙酰氧基庚烯酮和乙酰氧基十一酮，相关的C_9-19氧代烷基或氧代烯基分子被用于监测小蚜的种群水平，并通过破坏交配模式来控制小蚜种群。
• A heterogeneous gold(I)-catalyzed regioselective hydration of propargyl acetates toward α-acyloxy methyl ketones
  作者：Yingying Du、Fang Yao、Rongli Zhang、Mingzhong Cai

  DOI：10.1016/j.jorganchem.2020.121136

  日期：2020.3

  heterogeneous gold(I)-catalyzed regioselective hydration of propargyl acetates has been developed that proceeds smoothly in 1,4-dioxane at room temperature in the presence of 1 mol% diphenylphosphine-modified MCM-41-anchored gold(I) complex [Ph2P-MCM-41-AuSbF6] as catalyst and provides an efficient and practical approach for the synthesis of a variety of α-acyloxy methyl ketones with high atom economy

  已经开发出了炔丙基乙酸酯的多相金（I）催化区域选择性水合，可在室温下在1 mol％二苯膦改性的MCM-41固定的金（I）络合物存在下，在1,4-二恶烷中平稳进行。2 P-MCM-41-AuSbF 6 ]作为催化剂，为合成具有高原子经济性，良好至优异收率和高官能团耐受性的各种α-酰氧基甲基酮提供了一种高效实用的方法。这种新的固定化金（I）催化剂可以通过简单的制备程序轻松地从市售试剂中获得，并通过过滤过程进行回收，并至少重复使用7次，而活性没有明显降低。
• Iodobenzene-Catalyzed α-Acetoxylation of Ketones. In Situ Generation of Hypervalent (Diacyloxyiodo)benzenes Using <i>m</i>-Chloroperbenzoic Acid
  作者：Masahito Ochiai、Yasunori Takeuchi、Tomoko Katayama、Takuya Sueda、Kazunori Miyamoto

  DOI：10.1021/ja0542800

  日期：2005.9.1

  Reported here for the first time is the iodobenzene-catalyzed alpha-oxidation of ketones, in which diacyloxy(phenyl)-lambda3-iodanes generated in situ act as real oxidants of ketones and m-chloroperbenzoic acid serves as a terminal oxidant. Oxidation of a ketone with m-chloroperbenzoic acid in acetic acid in the presence of a catalytic amount of iodobenzene, BF3.Et2O, and water at room temperature under argon affords an alpha-acetoxy ketone in good yield. p-Methyl- and p-chloroiodobenzene also serve as efficient catalysts in this direct oxidation. We found that when the reaction was carried out in the absence of a catalytic amount of iodobenzene, Baeyer-Villiger oxidation of a ketone took place. It is noted that use of water and BF3.Et2O is crucial to the success of this alpha-acetoxylation.
• 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.
• Sakaguchi Satoshi, Watase Seiji, Katayama Yuji, Sakata Yasuyuki, Nishiyam+, J. Org. Chem, 59 (1994) N 19, S 5681-5686
  作者：Sakaguchi Satoshi, Watase Seiji, Katayama Yuji, Sakata Yasuyuki, Nishiyam+

  DOI：——

  日期：——