dimethyl 2-(1-methyl-2-oxo-2-phenylethylidene)malonate | 136579-79-8

• 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: dimethyl 2-(1-methyl-2-oxo-2-phenylethylidene)malonate
• 英文别名: Dimethyl (1-oxo-1-phenylpropan-2-ylidene)propanedioate；dimethyl 2-(1-oxo-1-phenylpropan-2-ylidene)propanedioate
• CAS: 136579-79-8
• 化学式: C₁₄H₁₄O₅
• 分子量: 262.262
• InChiKey: IPGGKCRXJYHFCB-UHFFFAOYSA-N

物化性质

• 沸点：
  331.1±42.0 °C(Predicted)
• 密度：
  1.191±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-Methoxy-5-methyl-1-phenyl-2,6,7-trioxa-bicyclo[3.2.0]hept-3-ene-4-carboxylic acid methyl ester 在 乙硫醚 作用下， 生成 dimethyl 2-(1-methyl-2-oxo-2-phenylethylidene)malonate
  参考文献：
  名称：

  A further selective pathway in thermal conversion of 2,5-epidioxy-2-alkoxy-2,5-dihydrofurans (2-alkoxyfuran endo-peroxides). Synthesis of the first 5-hydroperoxyfuran-2(5H)-ones

  摘要：

  表二氧基二氢呋喃 1 的热转化通过二氧杂环丁烷 3 生成立体异构二聚体 4，其与抗肿瘤环状过氧化物具有结构关系，是多种多官能化合物的方便起始材料；它们的弱酸水解为结构与生物活性产物相关的呋喃酮衍生物7和8的合成提供了方便的途径。

  DOI：

  10.1039/c39910001061

文献信息

• Photosensitized Oxidation of Furans; Part 18: A Simple Method for a One-Pot Synthesis of Functionalized Methyl cis-4-Oxoalk-2-enoates
  作者：M. Rosaria Iesce、Flavio Cermola、Alfonso Piazza、Rachele Scarpati、M. Liliana Graziano

  DOI：10.1055/s-1995-3922

  日期：1995.4

  Functionalized methyl cis-4-oxoalk-2-enoates 2 are synthesized in a one-pot procedure by singlet oxygen oxygenation of the corresponding 2-methoxyfurans 1 in methanol and reduction of the resulting hydroperoxides 4 and 5 by the sulfides 6 which are selectively oxidized into the sulfoxides 7. The synthetic method has a wide range of applicability and affords compounds 2 stereoselectively and in good yields; concomitantly the sulfoxides 7 are obtained in excellent yields.

  功能化的甲基顺-4-氧烯-2-酸酯2通过单氧对相应的2-甲氧基呋喃1在甲醇中的氧化，随后用硫化物6选择性还原生成的过氧化物4和5，采用一锅法合成。该合成方法具有广泛的适用性，能够立体选择性地高产量地获得化合物2；同时，亚砜7也以优异的产率获得。
• Intermolecular Mn(OAc)₃-Mediated Oxidative Free-Radical Reaction of Dimethyl Malonate or Ethyl Cyanoacetate with Allenes: An Efficient Synthesis of Furan-2(5<i>H</i>)-ones or Dimethyl 2-(2-Oxoethylidene)malonates
  作者：Xian Huang、Zhimeng Wu

  DOI：10.1055/s-2006-958925

  日期：2007.1

  Manganese(III)-mediated free-radical reaction of allenes with dimethyl malonate or ethyl cyanoacetate in acetic acid produces furan-2-(5//)-one derivatives (but-2-en-4-olides) or dimethyl 2-(2-oxoethylidene)malonates in moderate yields. The possible reaction mechanism is also discussed.

  锰 (III) 介导的丙二酸二甲酯或氰基乙酸乙酯在乙酸中的自由基反应产生 furan-2-(5//)-one 衍生物（but-2-en-4-olides）或二甲基 2-( 2-氧代亚乙基）丙二酸酯的产率适中。还讨论了可能的反应机理。
• A further selective pathway in thermal conversion of 2,5-epidioxy-2-alkoxy-2,5-dihydrofurans (2-alkoxyfuran endo-peroxides). Synthesis of the first 5-hydroperoxyfuran-2(5H)-ones
  作者：M. Rosaria Iesce、M. Liliana Graziano、Flavio Cermola、Rachele Scarpati

  DOI：10.1039/c39910001061

  日期：——

  Thermal conversion of the epidioxydihydrofurans 1 leads, via dioxetanes 3, to the stereoisomeric dimers 4 which have a structural relationship with antitumour cyclic peroxides and represent convenient starting materials for several multifunctional compounds; their mild acid hydrolysis provides a convenient entry to the synthesis of the furanone derivatives 7 and 8 which are structurally related to biologically active products.

  表二氧基二氢呋喃 1 的热转化通过二氧杂环丁烷 3 生成立体异构二聚体 4，其与抗肿瘤环状过氧化物具有结构关系，是多种多官能化合物的方便起始材料；它们的弱酸水解为结构与生物活性产物相关的呋喃酮衍生物7和8的合成提供了方便的途径。