2-chloro-N-(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)benzamide | 1344685-84-2

• 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: 2-chloro-N-(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)benzamide
• 英文别名: 2-Chloro-N-(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)benzamide；2-chloro-N-[2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl]benzamide
• CAS: 1344685-84-2
• 化学式: C₁₄H₅ClF₇NO
• 分子量: 371.642
• InChiKey: VCXLCKPYAMUGAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-chloro-N-(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)benzamide 在 dipotassium peroxodisulfate 、 碘 、 cesium acetate 、 palladium diacetate 作用下， 以 二甲基亚砜 为溶剂， 反应 16.0h， 以89%的产率得到2-chloro-6-iodo-N-[2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl]benzamide
  参考文献：
  名称：

  Pd(II)-Catalyzed C–H Iodination Using Molecular I₂ as the Sole Oxidant

  摘要：

  Pd-catalyzed ortho-C-H iodination directed by a weakly coordinating amide auxiliary using h as the sole oxidant was developed. This reaction is compatible with a wide range of heterocycles including pyridines, imidazoles, oxazoles, thiazoles, isoxazoles, and pyrazoles.

  DOI：

  10.1021/ja4055492
• 作为产物：
  描述：

  八氟甲苯 在 ammonium hydroxide 作用下， 以 1,4-二氧六环 、 水 、 甲苯 为溶剂， 反应 28.0h， 生成 2-chloro-N-(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)benzamide
  参考文献：
  名称：

  钯（II）催化苯甲酸的选择性辅助氟化的实用辅助：弱配位方法

  摘要：

  最后，一个选择！通过弱配位，首次实现了高选择性的钯（II）催化的邻一氟化反应（参见方案； Ar = 2,3,5,6-四氟-4-（三氟甲基）苯基）。对该协议进行简单修改即可在单氟化和二氟化之间进行选择。一氟和二氟苯甲酸衍生物在制药和农用化学工业中很有价值。

  DOI：

  10.1002/anie.201102985

文献信息

• Ligand-Promoted Alkylation of C(sp³)–H and C(sp²)–H Bonds
  作者：Ru-Yi Zhu、Jian He、Xiao-Chen Wang、Jin-Quan Yu

  DOI：10.1021/ja508165a

  日期：2014.9.24

  9-Methylacridine was identified as a generally effective ligand to promote a Pd(II)-catalyzed C(sp3)–H and C(sp2)–H alkylation of simple amides with various alkyl iodides. This alkylation reaction was applied to the preparation of unnatural amino acids and geometrically controlled tri- and tetrasubstituted acrylic acids.

  9-甲基吖啶被确定为一种普遍有效的配体，可促进 Pd(II) 催化的 C(sp3)-H 和 C(sp2)-H 与各种烷基碘的简单酰胺的烷基化。这种烷基化反应用于制备非天然氨基酸和几何控制的三和四取代丙烯酸。
• PALLADIUM(II)-CATALYZED SELECTIVE FLUORINATION OF BENZOIC ACIDS AND DERIVATIVES
  申请人：YU JIN-QUAN

  公开号：US20140018566A1

  公开（公告）日：2014-01-16

  A new method of ortho-fluorination for selectively fluorinating a benzoic acid or derivative compound where an aryl C—H bond is directly replaced by an aryl C—F bond is provided. The method comprises reacting a compound having the formula: wherein X is at least one substitution group attached with a benzene ring and Ar is an aromatic substitution group comprising at least one fluorine atom, and a mixture comprising a palladium (II) catalyst and a fluorinating reagent to form at least one of the ortho-fluorinated compounds having the formulae with good yield and selectivity.

  提供了一种新的正氟化方法，用于选择性氟化苯甲酸或衍生物化合物，其中芳基C—H键直接被芳基C—F键取代。该方法包括将具有以下结构的化合物与含有至少一种与苯环连接的取代基X和至少一种含有至少一个氟原子的芳基取代基Ar的混合物反应，其中X是至少一个取代基，Ar是至少含有一个氟原子的芳基取代基，以及一种钯(II)催化剂和氟化试剂的混合物，形成至少一种具有良好产率和选择性的正氟化化合物。
• Pd(II)-Catalyzed Ortho Trifluoromethylation of Arenes and Insights into the Coordination Mode of Acidic Amide Directing Groups
  作者：Xing-Guo Zhang、Hui-Xiong Dai、Masayuki Wasa、Jin-Quan Yu

  DOI：10.1021/ja305259n

  日期：2012.7.25

  A Pd(II)-catalyzed trifluoromethylation of ortho C-H bonds with an array of N-arylbenzamides derived from benzoic acids is reported. N-Methylformamide has been identified as a crucial promoter of C-CF3 bond formation from the Pd center. X-ray characterization of the C-H insertion intermediate has revealed a rare coordination mode of acidic amides as directing groups and the origin of their capacity in directing C-H activation.
• Ru(II)-Catalyzed <i>ortho</i>-C–H Amination of Arenes and Heteroarenes at Room Temperature
  作者：Ming Shang、Shao-Hang Zeng、Shang-Zheng Sun、Hui-Xiong Dai、Jin-Quan Yu

  DOI：10.1021/ol402515s

  日期：2013.10.18

  The Rupp-catalyzed ortho-C-H amination directed by a weakly coordinating amide auxiliary with O-benzoyl hydroxylamines at room temperature has been achieved. This reaction is compatible with heterocycles including pyrazole, thiophene, benzothiophene, furan, benzofuran, and indole.
• Pd-Catalyzed Oxidative <i>ortho</i>-C–H Borylation of Arenes
  作者：Hui-Xiong Dai、Jin-Quan Yu

  DOI：10.1021/ja2097095

  日期：2012.1.11

  The development of a Pd-catalyzed oxidative ortho-C-H borylation with N-arylbenzamides is reported. A modified dibenzylideneacetone (dba) ligand, a weak base, and a strong oxidant are critical for obtaining good yields. The reaction is tolerant of electron-deficient and electron-rich benzamides derived from readily available benzoic acids. The borylated products can be converted to various synthons via diverse transformations.