Ethyl 4-methyl-2-oxo-3-cyclopentene-1-carboxylate | 96302-37-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Ethyl 4-methyl-2-oxo-3-cyclopentene-1-carboxylate
• 英文别名: ethyl 1-methyl-3-oxocyclopentene-4-carboxylate；5-carboethoxy-3-methyl-2-cyclopentenone；Ethyl 4-methyl-2-oxocyclopent-3-ene-1-carboxylate
• CAS: 96302-37-3
• 化学式: C₉H₁₂O₃
• 分子量: 168.192
• InChiKey: KBDQTEPCYUWRCS-UHFFFAOYSA-N

物化性质

• 沸点：
  40-60 °C(Press: 0.1 Torr)
• 密度：
  1.116±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 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：

  Ethyl 4-methyl-2-oxo-3-cyclopentene-1-carboxylate 在 potassium tert-butylate 、 四氯化钛 作用下， 以 四氢呋喃 、 吡啶 、 四氯化碳 、 乙醚 、 叔丁醇 为溶剂， 反应 31.17h， 生成 6-carboethoxy-8-methyl-3-(dimethyl methylenedicarboxylate)bicyclo<4.3.0>nona-1,8-diene
  参考文献：
  名称：

  Hellou, Jocelyne; Berube, Grevais; Newlands, Michael J., Canadian Journal of Chemistry, 1988, vol. 66, p. 439 - 448

  摘要：

  DOI：
• 作为产物：
  描述：

  Ethyl 2-ethoxy-4-methyl-1,3-cyclopentadiene-1-carboxylate 在 盐酸 作用下， 以 氯仿 为溶剂， 以91%的产率得到Ethyl 4-methyl-2-oxo-3-cyclopentene-1-carboxylate
  参考文献：
  名称：

  亚丙基三苯基膦和α-卤代羰基化合物的环戊烯酮

  摘要：

  亚烷基三苯基磷烷3与α-卤代酮和α-卤代硫代酯反应，在碱的存在下，通过[3 + 2]环化过程得到2-乙氧基环戊二烯。2-乙氧基环戊二烯的弱酸处理为环戊烯酮提供了一条新途径。

  DOI：

  10.1016/0040-4039(91)80029-6

文献信息

• Diethyl Dicarbonate: A Convenient Reagent for the Preparation of β-Ketoesters
  作者：Jocelyne Hellou、John F. Kingston、Alex G. Fallis

  DOI：10.1055/s-1984-31056

  日期：——
• Allylidenetriphenylphosphorane as a bifunctional reagent: synthesis of cyclopentenones and .alpha.,.beta.-unsaturated ketones with [3-(alkoxycarbonyl)-2-ethoxy-2-propenylidene]triphenylphosphorane
  作者：Minoru Hatanaka、Yuichiro Himeda、Ritsuo Imashiro、Yasuhiro Tanaka、Ikuo Ueda

  DOI：10.1021/jo00080a019

  日期：1994.1

  When (3-(ethoxycarbonyl)-2-ethoxy-2-propenylidene) triphenylphosphorane (6) was allowed to react with cu-bromo ketones 8a-d in dichloromethane in the presence of Cs2CO3 at room temperature, a [3 + 2] annulation occurred and led to the formation of the corresponding 2-ethoxycyclopentadienes 9a-d in excellent yields. Similarly, bromo thioester 8g underwent the annulation to give 4-(ethylthio)-cyclopentadiene 9g. Secondary bromides 2-bromo-3-pentanone and 2-bromocyclohexanone also afforded tetrasubstituted cyclopentadienes 9e and 9f in moderate yields when 2 equiv of 6 was used. The annulation is believed to proceed through a sequence involving a stepwise alkylation at the gamma position of 6 and an intramolecular Wittig reaction because of the fact that intermediate 11 was isolated. The resulting 2-ethoxycyclopentadienes 9a-g were converted quantitatively into the corresponding cyclopentenones 10a-g upon mild acid treatment. Furthermore, allylidenetriphenylphosphorane underwent a carbon elongation at both ends of the three-carbon unit via an alkylation-Wittig reaction sequence. (3-(tert-Butoxycarbonyl)-2-ethoxy-2-propenylidene)triphenylphosphorane (7) reacted first with alkyl halides and then with aldehydes in the presence of Cs2CO3 to give enol ethers 23a-f, which were converted into alpha,beta-unsaturated ketones 20, 21, and 25c-f by hydrolysis of the enol ether and then decarboxylation. In this way, shogaol (29), the pungent principle component of ginger, was conveniently synthesized starting from 2-methoxy-4-methylphenol.
• HELLOU, J.;KINGSTON, J. F.;FALLIS, A. G., SYNTHESIS, BRD, 1984, N 12, 1014-1017
  作者：HELLOU, J.、KINGSTON, J. F.、FALLIS, A. G.

  DOI：——

  日期：——
• HELLOU, JOCELYNE;BERUBE, GERVAIS;NEWLANDS, MICHAEL J.;FALLIS, ALEX G.;GAB+, CAN. J. CHEM., 66,(1988) N 3, 439-448
  作者：HELLOU, JOCELYNE、BERUBE, GERVAIS、NEWLANDS, MICHAEL J.、FALLIS, ALEX G.、GAB+

  DOI：——

  日期：——