2,2,2-trifluoro-1-phenylethyl 2-naphthoate | 1228172-17-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,2,2-trifluoro-1-phenylethyl 2-naphthoate
• 英文别名: (2,2,2-Trifluoro-1-phenylethyl) naphthalene-2-carboxylate；(2,2,2-trifluoro-1-phenylethyl) naphthalene-2-carboxylate
• CAS: 1228172-17-5
• 化学式: C₁₉H₁₃F₃O₂
• 分子量: 330.306
• InChiKey: CQIURXWJYHAGJU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,2,2-三氟苯乙酮 、 2-萘甲醛 在 3-(三氟甲基)苯硫酚 、 苯基溴化镁 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 24.0h， 以86%的产率得到2,2,2-trifluoro-1-phenylethyl 2-naphthoate
  参考文献：
  名称：

  可调谐的溴化镁硫氰酸盐Tishchenko反应催化剂：分子间醛-三氟甲基酮偶联

  摘要：

  应用知识：受生化过程启发的硫醇盐催化的新的Tishchenko反应具有对催化剂的空间/电子性质的出色控制。反应中间体的分离为反应机理提供了有价值的见解，这反过来又使醛与活化酮之间的第一个交叉-蒂申科偶合反应得以发展（参见示例）。

  DOI：

  10.1002/anie.200907167

文献信息

• Tunable Bromomagnesium Thiolate Tishchenko Reaction Catalysts: Intermolecular Aldehyde-Trifluoromethylketone Coupling
  作者：Linda Cronin、Francesco Manoni、Cornelius J. O' Connor、Stephen J. Connon

  DOI：10.1002/anie.200907167

  日期：——

  thiolate‐catalyzed Tishchenko reaction inspired by biochemical processes features exceptionally good control over the catalyst's steric/electronic properties. The isolation of reaction intermediates provided valuable insights into the reaction mechanism, which in turn has allowed the development of the first cross‐Tishchenko coupling reactions between aldehydes and activated ketones (see example).

  应用知识：受生化过程启发的硫醇盐催化的新的Tishchenko反应具有对催化剂的空间/电子性质的出色控制。反应中间体的分离为反应机理提供了有价值的见解，这反过来又使醛与活化酮之间的第一个交叉-蒂申科偶合反应得以发展（参见示例）。
• Selenide Ions as Catalysts for Homo- and Crossed-Tishchenko Reactions of Expanded Scope
  作者：Simon P. Curran、Stephen J. Connon

  DOI：10.1021/ol203439g

  日期：2012.2.17

  Selenide ions have been shown to catalyze the Tishchenko reaction for the first time. These catalysts are superior to previously reported thiolate analogues and promote the disproportionation of aldehydes with increased reaction rates and broader scope at lower catalyst loadings and temperatures. Significantly improved catalyst performance was also observed in the aryl selenide mediated crossed intermolecular Tishchenko reaction.
• Synthesis, Characterization, and Unique Catalytic Activities of a Fluorinated Nickel Enolate
  作者：Ryohei Doi、Kotaro Kikushima、Masato Ohashi、Sensuke Ogoshi

  DOI：10.1021/ja511730k

  日期：2015.3.11

  We have synthesized a new nickel enolate [(PhCOCF2)Ni(dcpe)][FB(C6F5)(3)] featuring fluorine atoms on the enolate moiety via B(C6F5)(3)-promoted C-F bond activation of alpha,alpha,alpha-trifluoroacetophenone. X-ray diffraction study of [(PhCOCF2)Ni(dcpe)][FB(C6F5)(3)] revealed that the complex had adopted an eta(3)-oxallyl coordination mode in the crystal lattice. The reaction of (BuNC)-Bu-t with [(PhCOCF2)Ni(dcpe)][FB(C6F5)(3)] resulted in the coordination of isocyanide to the nickel center to form a C-bound enolate complex. The reactions of [(PhCOCF2)Ni(dcpe)][FB(C6F5)(3)] with aldehydes gave insertion products quantitatively which were fully characterized by NMR spectroscopy. Furthermore, we established unique catalytic applications for [(PhCOCF2)Ni(dcpe)][FB(C6F5)(3)] toward a Tishchenko reaction, along with a highly selective crossed-esterification of alpha,alpha,alpha-trifluoroacetophenones with aldehydes.