4,5-Dimethyl-5-phenyl-dihydro-furan-2-one | 74603-51-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 4,5-Dimethyl-5-phenyl-dihydro-furan-2-one
• 英文别名: 4,5-Dimethyl-5-phenyloxolan-2-one
• CAS: 74603-51-3
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: CKHUTFYWZDXUOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  在 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 4,5-Dimethyl-5-phenyl-dihydro-furan-2-one
  参考文献：
  名称：

  Three carbon annelation reagents: unsaturated alpha aminonitriles as homoenolate equivalents

  摘要：

  DOI：

  10.1016/s0040-4039(00)71371-2

文献信息

• Electroreductive coupling of aromatic ketones, aldehydes, and aldimines with α,β-unsaturated esters: Synthesis of 5-aryl substituted γ-butyrolactones and lactams
  作者：Naoki Kise、Yusuke Hamada、Toshihiko Sakurai

  DOI：10.1016/j.tet.2017.01.013

  日期：2017.2

  The electroreductive intermolecular coupling of aromatic ketones and aldehydes with α,β-unsaturated esters in the presence of TMSCl gave the adducts as γ-trimethylsiloxy esters. The detrimethylsilylation of the adducts with TBAF afforded 5-aryl substituted γ-butyrolactones. The electroreductive coupling of N-(4-methoxyphenyl)-1-arylmethaneimines with methyl acrylate in the presence of TMSCl gave the

  在TMCSC1存在下，芳族酮和醛与α，β-不饱和酯的电还原分子间偶联产生加合物，为γ-三甲基甲硅烷氧基酯。用TBAF将加合物的三甲基甲硅烷基化得到5-芳基取代的γ-丁内酯。N的电耦合-（4-甲氧基苯基）-1-芳基亚甲基与TMSCl存在下的丙烯酸甲酯得到加合物，为4-芳基-4-（（4-甲氧基苯基）氨基）丁酸甲酯。通过用NaH环化并随后用CAN氧化，将加合物转化为5-芳基-γ-丁内酰胺。通过该方法由烟醛制备（±）-烟碱。在TMCSC1存在下，芳族酮和醛亚胺与丙烯腈的电还原偶联分别得到4-芳基-4-（三甲基甲硅烷氧基）丁腈和4-芳基-4-（（4-甲氧基苯基）氨基）丁腈。
• Unexpected Ti^III/Mn-Promoted Pinacol Coupling of Ketones
  作者：Miguel Paradas、Araceli G. Campaña、Rosa E. Estévez、Luis Álvarez de Cienfuegos、Tania Jiménez、Rafael Robles、Juan M. Cuerva、J. Enrique Oltra

  DOI：10.1021/jo9005238

  日期：2009.5.1

  Titanocene(III) chemistry has emerged in the last decades as an indispensable tool in C-C bond-forming reactions. In this context, pinacol and related reactions allow the stereoselective synthesis of vicinal diols. In this work, we present new applications of these reactions using as starting materials aromatic ketones. Simple and smooth reaction conditions have been developed and have been applied for inter- and intramolecular processes. We also describe that although Cp2TiCl is usually used as a monoelectronic reducing agent, it can be also used as an efficient Lewis acid.
• Yukhno, F. A.; Bikkulov, A. Z.; Yukhno, G. F., Journal of applied chemistry of the USSR, 1982, vol. 55, # 2, p. 377 - 380
  作者：Yukhno, F. A.、Bikkulov, A. Z.、Yukhno, G. F.

  DOI：——

  日期：——
• JACOBSON R. M.; CLADER J. W., TETRAHEDRON LETT., 1980, 21, NO 13, 1205-1208
  作者：JACOBSON R. M.、 CLADER J. W.

  DOI：——

  日期：——
• Three carbon annelation reagents: unsaturated alpha aminonitriles as homoenolate equivalents
  作者：Richard M. Jacobson、John W. Clader

  DOI：10.1016/s0040-4039(00)71371-2

  日期：——