2-Oxo-1-p-tolylethynyl-cyclopentanecarboxylic acid ethyl ester | 852142-49-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-Oxo-1-p-tolylethynyl-cyclopentanecarboxylic acid ethyl ester
• 英文别名: Ethyl 2-oxo-1-(p-tolylethynyl)-cyclopentane-1-carboxylate；ethyl 1-[2-(4-methylphenyl)ethynyl]-2-oxocyclopentane-1-carboxylate
• CAS: 852142-49-5
• 化学式: C₁₇H₁₈O₃
• 分子量: 270.328
• InChiKey: USRGWUBVZGYNTA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 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-Oxo-1-p-tolylethynyl-cyclopentanecarboxylic acid ethyl ester 在 2,6-二甲基吡啶 、 三氟甲磺酸三甲基硅酯 、 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 反应 147.0h， 生成
  参考文献：
  名称：

  Trimethylaluminium-induced diastereoselective methylation onto ethyl 2-oxocyclopentane-1-carboxylate and isomerization between the dimethylaluminium-alkoxide products

  摘要：

  Methylation of alpha-disubstituted cyclopentanone 1 with Me3Al in CH2Cl2 at 0 degrees C for 30 min gave diastereoselectively a mixture of (1R*,2S*)-2 and (1R*,2R*)-2 in a 96:4 ratio and 83% total yield. When the same methylation was carried out at 0 degrees C for 1 h and then at room temperature for 120 h, a diastereomeric mixture of (1R*,2S*)-2 and (1R*,2R*)-2 was obtained in a 12:88 ratio and in 88% total yield. The stereochemistry of the two diastereomers was determined by the results of acetalization of their diol derivatives 3 and 5. lsomerization between the Me2Al-alkoxides of (1R*,2S*)-2 and (1R*,2R*)-2 and its possible mechanism were investigated by HPLC analysis of the methylation reaction process at 0 degrees C for 1 h and then at room temperature for 56 h and also by their Mutual epimerization reactions. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.02.142
• 作为产物：
  描述：

  2-氧代环戊羧酸乙酯 、 4-甲苯基乙炔 在 正丁基锂 、 lead(IV) acetate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.92h， 生成 2-Oxo-1-p-tolylethynyl-cyclopentanecarboxylic acid ethyl ester
  参考文献：
  名称：

  Facile generation method for conjugated allenyl esters based on retro-Dieckmann-type ring-opening reactions

  摘要：

  alpha-Alkynyl-alpha-ethoxycarbonyl cyclopentanones 1a-c and cyclohexanones 2a-c were readily synthesized by the reaction of ethyl 2-oxocyclopentanonecarboxylate 6 and ethyl 2-oxocyclohexanonecarboxylate 7 with alkynyllead triacetates 5a-c obtained from lithium acetylides 4a-c and lead tetraacetate. Treatment of 1a-c and 2a-c with 1 N KOH in THF or with n-Bu4N+OEt+ in EtOH and THF gave the corresponding conjugated allenyl esters 8a-c, 9a-c, 10a-c, and 11a-c in good to excellent yields, respectively. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.02.138

文献信息

• Trimethylaluminium-induced diastereoselective methylation onto ethyl 2-oxocyclopentane-1-carboxylate and isomerization between the dimethylaluminium-alkoxide products
  作者：Shigeki Sano、Hisashi Shimizu、Yoshimitsu Nagao

  DOI：10.1016/j.tetlet.2005.02.142

  日期：2005.4

  Methylation of alpha-disubstituted cyclopentanone 1 with Me3Al in CH2Cl2 at 0 degrees C for 30 min gave diastereoselectively a mixture of (1R*,2S*)-2 and (1R*,2R*)-2 in a 96:4 ratio and 83% total yield. When the same methylation was carried out at 0 degrees C for 1 h and then at room temperature for 120 h, a diastereomeric mixture of (1R*,2S*)-2 and (1R*,2R*)-2 was obtained in a 12:88 ratio and in 88% total yield. The stereochemistry of the two diastereomers was determined by the results of acetalization of their diol derivatives 3 and 5. lsomerization between the Me2Al-alkoxides of (1R*,2S*)-2 and (1R*,2R*)-2 and its possible mechanism were investigated by HPLC analysis of the methylation reaction process at 0 degrees C for 1 h and then at room temperature for 56 h and also by their Mutual epimerization reactions. (c) 2005 Elsevier Ltd. All rights reserved.
• Facile generation method for conjugated allenyl esters based on retro-Dieckmann-type ring-opening reactions
  作者：Shigeki Sano、Hisashi Shimizu、Yoshimitsu Nagao

  DOI：10.1016/j.tetlet.2005.02.138

  日期：2005.4

  alpha-Alkynyl-alpha-ethoxycarbonyl cyclopentanones 1a-c and cyclohexanones 2a-c were readily synthesized by the reaction of ethyl 2-oxocyclopentanonecarboxylate 6 and ethyl 2-oxocyclohexanonecarboxylate 7 with alkynyllead triacetates 5a-c obtained from lithium acetylides 4a-c and lead tetraacetate. Treatment of 1a-c and 2a-c with 1 N KOH in THF or with n-Bu4N+OEt+ in EtOH and THF gave the corresponding conjugated allenyl esters 8a-c, 9a-c, 10a-c, and 11a-c in good to excellent yields, respectively. (c) 2005 Elsevier Ltd. All rights reserved.