1,1,1,3,3,3-hexafluoropropan-2-yl 4-nitrobenzoate | 401934-57-4

• 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: 1,1,1,3,3,3-hexafluoropropan-2-yl 4-nitrobenzoate
• CAS: 401934-57-4
• 化学式: C₁₀H₅F₆NO₄
• 分子量: 317.144
• InChiKey: TVDPNCLYRNJPDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1,1,1,3,3,3-hexafluoropropan-2-yl 4-nitrobenzoate 、 苄胺 以 乙腈 为溶剂， 反应 1.0h， 以96%的产率得到N-苄基-4-硝基苯甲酰胺
  参考文献：
  名称：

  TEMPO-Catalyzed Oxidative Amidation of Alcohols via Hexa­fluoroisopropyl Esters

  摘要：

  Stepwise oxidative amidation of alcohols using trichloroisocyanuric acid, a catalytic amount of TEMPO in combination with pyridine and hexafluoroisopropyl (HFIP) alcohol followed by amines is described. This procedure used HFIP esters as activating esters which were found to be very efficient acylating agents for amide bond formation. This process is compatible with a number of functional groups and acid-sensitive protecting groups.

  DOI：

  10.1055/s-0034-1381056
• 作为产物：
  描述：

  对硝基苯甲醇 、 六氟异丙醇 在 2,2,6,6-四甲基哌啶氧化物 、 三氯异氰尿酸 、 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 以93%的产率得到1,1,1,3,3,3-hexafluoropropan-2-yl 4-nitrobenzoate
  参考文献：
  名称：

  TEMPO-Catalyzed Oxidative Amidation of Alcohols via Hexa­fluoroisopropyl Esters

  摘要：

  Stepwise oxidative amidation of alcohols using trichloroisocyanuric acid, a catalytic amount of TEMPO in combination with pyridine and hexafluoroisopropyl (HFIP) alcohol followed by amines is described. This procedure used HFIP esters as activating esters which were found to be very efficient acylating agents for amide bond formation. This process is compatible with a number of functional groups and acid-sensitive protecting groups.

  DOI：

  10.1055/s-0034-1381056

文献信息

• Direct Esterification of Carboxylic Acids with Perfluorinated Alcohols Mediated by XtalFluor-E
  作者：Mathilde Vandamme、Léa Bouchard、Audrey Gilbert、Massaba Keita、Jean-François Paquin

  DOI：10.1021/acs.orglett.6b03365

  日期：2016.12.16

  The direct esterification of carboxylic acids with perfluorinated alcohols mediated by XtalFluor-E is reported. The corresponding polyfluorinated esters are obtained in moderate to excellent yields with a broad range of carboxylic acids, including aromatic, heteroaromatic, aliphatic, and nonracemic chiral substrates, using only a slight excess (2 equiv) of the perfluorinated alcohol. Control experiments

  据报道，由XtalFluor-E介导的羧酸与全氟化醇直接酯化。仅使用稍微过量的（2当量）全氟化醇，就可以以中等到极高的收率，用宽范围的羧酸（包括芳族，杂芳族，脂族和非外消旋手性底物）获得相应的多氟化酯。对照实验表明，该反应不通过的酰基氟化物的形成继续进行，但最有可能通过一个（二乙基氨基）二氟- λ 4硫烷基羧酸盐中间体。
• Oxidative Esterification of Aldehydes Using a Recyclable Oxoammonium Salt
  作者：Christopher B. Kelly、Michael A. Mercadante、Rebecca J. Wiles、Nicholas E. Leadbeater

  DOI：10.1021/ol400785d

  日期：2013.5.3

  aldehydes to hexafluoroisopropyl (HFIP) esters using the oxoammonium salt 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate (1a) is reported. These esters can be readily transformed into a variety of other functional groups. The spent oxidant (1b) can be recovered and conveniently reoxidized to regenerate the oxoammonium salt, 1a.

  报道了一种简单，高产，快速的路线，可使用4-乙酰氨基-2,2,6,6-四甲基哌啶-1-氧代四氟硼酸氧铵盐（1a）将多种醛氧化酯化为六氟异丙基（HFIP）酯。。这些酯可以容易地转化成多种其他官能团。可以回收用过的氧化剂（1b）并方便地将其重新氧化，以再生氧铵盐1a。
• Preparation of hexafluoroisopropyl esters by oxidative esterification of aldehydes using sodium persulfate
  作者：Arturo León Sandoval、Fabrizio Politano、Mason L. Witko、Nicholas E. Leadbeater

  DOI：10.1039/d1ob00251a

  日期：——

  A simple, metal-free route for the oxidative esterification of aldehydes to yield hexafluoroisopropyl esters is reported. The methodology employs sodium persulfate and a catalytic quantity of a nitroxide and is applicable to aromatic, heteroaromatic, and aliphatic aldehydes.

  报道了一种简单的，无金属的醛氧化酯化反应生成六氟异丙基酯的途径。该方法使用过硫酸钠和催化量的一氧化氮，并且适用于芳族，杂芳族和脂族醛。
• TEMPO-Catalyzed Oxidative Amidation of Alcohols via Hexa­fluoroisopropyl Esters
  作者：Jean-Michel Vatèle

  DOI：10.1055/s-0034-1381056

  日期：——

  Stepwise oxidative amidation of alcohols using trichloroisocyanuric acid, a catalytic amount of TEMPO in combination with pyridine and hexafluoroisopropyl (HFIP) alcohol followed by amines is described. This procedure used HFIP esters as activating esters which were found to be very efficient acylating agents for amide bond formation. This process is compatible with a number of functional groups and acid-sensitive protecting groups.