2-ethoxy-3-ethyl-2-cyclopentenone | 87362-93-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 乙烯酯类
• 英文名称: 2-ethoxy-3-ethyl-2-cyclopentenone
• 英文别名: 2-Ethoxy-3-ethylcyclopent-2-en-1-one
• CAS: 87362-93-4
• 化学式: C₉H₁₄O₂
• 分子量: 154.209
• InChiKey: UUXFEBLCVSILGB-UHFFFAOYSA-N

物化性质

• 沸点：
  255.4±39.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-ethoxy-3-ethyl-2-cyclopentenone 、 3-溴丙烯 在 manganese triacetate 作用下， 以 苯 为溶剂， 反应 12.0h， 以72%的产率得到5-allyl-2-ethoxy-3-ethyl-cyclopent-2-enone
  参考文献：
  名称：

  Mn(III)-based C–C bond formation: regioselective α′-allylation of various α,β-unsaturated, α and β-alkoxy α,β-unsaturated ketones

  摘要：

  The Manganese(III) -based regioselective alpha'-keto radical generation of unsaturated ketones is a versatile synthetic procedure with broad applicability. The generated alpha'-keto radical slowly creates a metal enolate in a solvent at reflux. The resultant metal enolate affords the corresponding alpha'-allylated alpha,beta-unsaturated ketones in good yields. This method is the first example of the metal mediated regioselective alpha'-allylation of alpha,beta-unsaturated ketones. The ketones that have alpha or beta-alkoxy groups also work efficiently. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.06.031
• 作为产物：
  描述：

  3-(2'-chlorovinyl)-2-hydroxy-2-cyclopentenone 生成 2-ethoxy-3-ethyl-2-cyclopentenone
  参考文献：
  名称：

  TSUBOI, SADAO;ARISAWA, KATSUJI;TAKEDA, AKIRA;SATO, SADAO;TAMURA, CHIHIRO, TETRAHEDRON LETT., 1983, 24, N 238, 2393-2394

  摘要：

  DOI：

文献信息

• Revision of the structure of the reaction product of chloral with α-acetylcyclopentanone in the presence of base
  作者：Sadao Tsuboi、Katsuji Arisawa、Akira Takeda、Sadao Sato、Chihiro Tamura

  DOI：10.1016/s0040-4039(00)81934-6

  日期：1983.1

  The structure of the product from the title reaction has been revised by means of 13C NMR, X-ray crystallographic analysis as well as additional chemical transformations.

  来自标题反应的产物的结构已通过13 C NMR，X射线晶体学分析以及其他化学转化方法进行了修改。
• Manganese(III) acetate based tandem oxidation of various α and β-alkoxy α,β-unsaturated ketones
  作者：Cihangir Tanyeli、Devrim Özdemirhan、Bengü Sezen

  DOI：10.1016/s0040-4020(02)01350-9

  日期：2002.12

  We described the unusual results of manganese(III) acetate based tandem oxidation of various alpha and beta-alkoxy alpha,beta-unsaturated ketones to afford the corresponding alpha'-acetoxy-alpha'-phenyl substituted oxidation products in good yields. The tandem oxidation to monoacetoxylation ratio can be tuned by the amount of manganese(III) acetate. (C) 2002 Elsevier Science Ltd. All rights reserved.