3,3-dimethylbutyric acid pentafluorophenyl ester | 957049-08-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 3,3-dimethylbutyric acid pentafluorophenyl ester
• 英文别名: (2,3,4,5,6-Pentafluorophenyl) 3,3-dimethylbutanoate
• CAS: 957049-08-0
• 化学式: C₁₂H₁₁F₅O₂
• 分子量: 282.21
• InChiKey: GHGGOSWSYNREPE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  1.0
• 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：
  7

反应信息

• 作为反应物：
  描述：

  3,3-dimethylbutyric acid pentafluorophenyl ester 、 2-甲基环己酮 在 magnesium bromide ethyl etherate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以62%的产率得到2-(3,3-dimethylbutyryl)-6-methylcyclohexanone
  参考文献：
  名称：

  MgBr₂·OEt₂-Promoted Coupling of Ketones and Activated Acyl Donors via Soft Enolization: A Practical Synthesis of 1,3-Diketones

  摘要：

  酮在与MgBr2·OEt2、i-Pr2NEt和各种酸酐处理时发生温和的烯醇化和酰化反应，生成1,3-二酮。该过程对N-酰基苯并三唑和O-五氟苯基酯特别高效，并且在这些情况下，使用未处理的试剂级CH2Cl2在开放空气中进行，从而提供了一种极其简单的方法来合成这一重要化合物类。

  DOI：

  10.1055/s-2008-1042947
• 作为产物：
  描述：

  3,3-二甲基-1-丁酸 、 五氟苯酚 在 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 12.0h， 以90%的产率得到3,3-dimethylbutyric acid pentafluorophenyl ester
  参考文献：
  名称：

  Direct Carbon−Carbon Bond Formation via Soft Enolization:  A Facile and Efficient Synthesis of 1,3-Diketones

  摘要：

  Ketones undergo soft enolate formation and acylation on treatment with MgBr2 center dot OE2, i-Pr2NEt, and various acylating agents to give 1,3-diketones. The process is particularly efficient for N-acylbenzotriazoles and O-Pfp esters, and, in these cases, is conducted with untreated, reagent-grade CH2Cl2 open to the air, thus providing an exceptionally simple approach to the synthesis of this important class of compounds.

  DOI：

  10.1021/ol701599v

文献信息

• Direct Carbon−Carbon Bond Formation via Soft Enolization:  A Facile and Efficient Synthesis of 1,3-Diketones
  作者：Daniel Lim、Fang、Guoqiang Zhou、Don M. Coltart

  DOI：10.1021/ol701599v

  日期：2007.10.1

  Ketones undergo soft enolate formation and acylation on treatment with MgBr2 center dot OE2, i-Pr2NEt, and various acylating agents to give 1,3-diketones. The process is particularly efficient for N-acylbenzotriazoles and O-Pfp esters, and, in these cases, is conducted with untreated, reagent-grade CH2Cl2 open to the air, thus providing an exceptionally simple approach to the synthesis of this important class of compounds.
• MgBr₂·OEt₂-Promoted Coupling of Ketones and Activated Acyl Donors via Soft Enolization: A Practical Synthesis of 1,3-Diketones
  作者：Don Coltart、Daniel Lim、Guoqiang Zhou、Alexandra Livanos、Fang Fang

  DOI：10.1055/s-2008-1042947

  日期：——

  Ketones undergo soft enolization and acylation on treatment with MgBr2·OEt2, i-Pr2NEt, and various acylating agents to give 1,3-diketones. The process is particularly efficient for N-acylbenzotriazoles and O-pentafluorophenyl esters, and, in these cases, is conducted using untreated, reagent grade CH2Cl2 open to the air, thus providing an exceptionally simple approach to the synthesis of this important class of compounds.

  酮在与MgBr2·OEt2、i-Pr2NEt和各种酸酐处理时发生温和的烯醇化和酰化反应，生成1,3-二酮。该过程对N-酰基苯并三唑和O-五氟苯基酯特别高效，并且在这些情况下，使用未处理的试剂级CH2Cl2在开放空气中进行，从而提供了一种极其简单的方法来合成这一重要化合物类。