2,2,3-trimethyl-4-oxo-cyclopentanecarboxylic acid ethyl ester | 1610852-08-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,2,3-trimethyl-4-oxo-cyclopentanecarboxylic acid ethyl ester
• 英文别名: Ethyl 2,2,3-trimethyl-4-oxocyclopentane-1-carboxylate
• CAS: 1610852-08-8
• 化学式: C₁₁H₁₈O₃
• 分子量: 198.262
• InChiKey: ITSHSKCZIUBANT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 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：

  2,2,3-trimethyl-4-oxo-cyclopentanecarboxylic acid ethyl ester 在 吡啶 、 咪唑 、 bis-triphenylphosphine-palladium(II) chloride 、 草酰氯 、 dimethyl sulfide borane 、 溴 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 N,N-二甲基甲酰胺 、 lithium hydroxide 、 (S)-2-甲基-CBS-恶唑硼烷 作用下， 以 四氢呋喃 、 四氯化碳 、 二氯甲烷 、 N,N-二甲基乙酰胺 、 水 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 120.5h， 生成 (3S)-7-bromo-1'-[tert-butyl(dimethyl)silyl]oxy-4',4'-dimethyl-5'-methylidenespiro[1H-indole-3,3'-cyclopentene]-2-one
  参考文献：
  名称：

  对柑桔素的合成研究：对映体制备高级螺吡氧吲哚中间体。

  摘要：

  这份手稿描述了螺环吲哚的对映体选择性制备方法，该方法适合提升至Citrinadin A或B的水平。

  DOI：

  10.1016/j.tet.2014.02.046

文献信息

• Synthesis of the Grape Mealybug Pheromone trans-alpha-Necrodyl Isobutyrate
  申请人：Trécé Inc.

  公开号：US20210206711A1

  公开（公告）日：2021-07-08

  Methods are provided for synthesizing the grape mealybug pheromone, trans-α-necrodyl isobutyrate, starting with essential plant oils that contain trans-α-necrodyl acetate. The synthesis method, in two steps, converts the trans-α-necrodyl acetate to trans-α-necrodol and then converts the trans-α-necrodol to the desired trans-α-necrodyl isobutyrate. The first step can be achieved by either of a hydrolysis reaction or a reduction reaction. In the hydrolysis reaction, the essential oil is mixed in an alcohol solvent with a hydroxide base, or by mixing the essential oil in an aqueous acid. A reduction reaction can instead by performed in an organic solvent in the presence of a reducing agent. The trans-α-necrodol is converted to the desired trans-α-necrodyl isobutyrate by an esterification reaction with a carboxylic acid, an acyl halide, or an acid anhydride.
• [EN] SYNTHESIS OF THE GRAPE MEALYBUG PHEROMONE TRANS-ALPHA-NECRODYL ISOBUTYRATE<br/>[FR] SYNTHÈSE DE LA PHÉROMONE DES COCHENILLES DE LA VIGNE, L'ISOBUTYRATE TRANS-ALPHA-NÉCRODYLE
  申请人：TRECE INC

  公开号：WO2021137994A1

  公开（公告）日：2021-07-08

  Methods are provided for synthesizing the grape mealybug pheromone, trans-alpha-necrodyl isobutyrate, starting with essential plant oils that contain trans-alpha-necrodyl acetate. The synthesis method, in two steps, converts the trans-alpha-necrodyl acetate to trans-alpha-necrodol and then converts the trans-alpha-necrodol to the desired trans-alpha-necrodyl isobutyrate. The first step can be achieved by either of a hydrolysis reaction or a reduction reaction. In the hydrolysis reaction, the essential oil is mixed in an alcohol solvent with a hydroxide base, or by mixing the essential oil in an aqueous acid. A reduction reaction can instead by performed in an organic solvent in the presence of a reducing agent. The trans-alpha-necrodol is converted to the desired trans-alpha-necrodyl isobutyrate by an esterification reaction with a carboxylic acid, an acyl halide, or an acid anhydride.