2’,5’-dimethylpivalanilide | 70298-82-7

• 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’,5’-dimethylpivalanilide
• 英文别名: N-(2,5-Dimethylphenyl)-pivalamid；N-(2,5-dimethylphenyl)-2,2-dimethylpropanamide
• CAS: 70298-82-7
• 化学式: C₁₃H₁₉NO
• mdl: MFCD00459293
• 分子量: 205.3
• InChiKey: NKYBYQIOVVDXQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.461
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2’,5’-dimethylpivalanilide 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成 2-(tert-butyl)-6-methyl-1H-indole
  参考文献：
  名称：

  阻转异构体芳基-对-奎宁酮的有机催化对映选择性合成：面向多元联苯二酚合成的平台分子。

  摘要：

  这里介绍的是一类新型的轴向手性芳基对苯二酚，作为制备非C 2对称联芳基二醇的平台分子。两套芳基的p通过手性磷酸的装置具有显着的enantiocontrol合成-quinone框架催化对映选择性芳基化p通过中央到外轴手性转换-quinones。然后，这些芳基对苯醌被用于获得具有高度保留的对映体纯度的各种高度官能化的非C 2对称联芳基二醇。

  DOI：

  10.1002/anie.202004671
• 作为产物：
  描述：

  N-(m-tolyl)pivalamide 、 5-甲基-5H-二苯并[B,D]噻吩-5-三氟甲烷磺酸盐 在 palladium diacetate 、 copper(II) acetate monohydrate 、 三氟乙酸 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 6.0h， 以84%的产率得到2’,5’-dimethylpivalanilide
  参考文献：
  名称：

  ulf盐作为烷基化剂，用于钯催化的苯甲酸酯和芳香尿素的直接邻位烷基化

  摘要：

  开发了一种通过C–H活化对乙酰苯胺和芳香族脲衍生物进行邻位烷基化的新方法。烷基二苯并噻吩鎓盐被认为是钯催化的C–H活化反应的新试剂，该反应能够在温和的催化条件下将甲基和其他烷基从salt盐转移至苯胺衍生物。

  DOI：

  10.1021/acs.orglett.7b03813

文献信息

• Divergent Regioselective Csp²–H Difluoromethylation of Aromatic Amines Enabled by Nickel Catalysis
  作者：Quan Gou、Qianqiong Chen、Qiujian Tan、Minghong Zhu、Huisheng Huang、Mengjiao Deng、Wei Yi、Shuhua He

  DOI：10.1021/acs.orglett.2c01262

  日期：2022.5.20

  bidentate phosphine ligand, offering an invaluable synthesis means to construct extensive p-difluoromethylated products and difluorooxindole derivatives with significant functional fragments. Furthermore, the gram-scale reaction, broad substrate scope, excellent functional-group compatibility, late-stage difluoromethylation of pesticides, and even formal synthesis of HDAC6 inhibitors further demonstrate the

  在此，在二齿膦配体的帮助下，开发了第一个用于镍催化的各种芳族胺的邻位或对位二氟甲基化的催化方案，为构建广泛的对二氟甲基化产物和具有重要功能片段的二氟羟吲哚衍生物提供了宝贵的合成方法。 . 此外，克级反应、广泛的底物范围、优异的官能团相容性、农药的后期二氟甲基化，甚至HDAC6抑制剂的正式合成进一步证明了该方法的实用性。
• 10.1039/d4gc01997k
  作者：Gou, Quan、Yu, Mengting、Chen, Qianqiong、Gu, Chengyi、Zhu, Qianhua、Ding, Ruoxi、Tang, Mi、Zhao, Qingsheng、Shi, Jianwei、Huang, Huisheng

  DOI：10.1039/d4gc01997k

  日期：——

  environmentally friendly modular platform for the sustainable para-difluoromethylation of readily available aromatic amines via a metal-free photocatalytic system. The reaction, for the first time, exhibits excellent functional group tolerance and broad substrate scope with a radical–radical coupling C–H functionalization strategy, rapidly delivering a variety of valuable difluoromethylated products. Furthermore

  尽管二氟亚甲基片段在医学、农业化学和材料科学中很重要，但芳环的精确且可持续的 C-H 二氟甲基化仍然是一个挑战。如果方法像金属催化一样可靠和模块化，那么室温下无金属二氟甲基化的研究将会取得进展。在此，我们提出了一种绿色环保的模块化平台，用于通过无金属光催化系统对容易获得的芳香胺进行可持续的对二氟甲基化。该反应首次通过自由基-自由基耦合C-H官能化策略表现出优异的官能团耐受性和广泛的底物范围，快速产生各种有价值的二氟甲基化产物。此外，各种具有高原子经济性的复杂分子的衍生化进一步证明了该方案的合成效用和实用性。一系列实验研究和 DFT 计算证实了合理的反应机制。
• Sc(OTf)₃-Catalyzed Synthesis of Symmetrical Dithioacetals and Bisarylmethanes Using Nitromethane as a Methylene Source
  作者：Dattatraya H. Dethe、Manmohan Shukla、Balu D. Dherange

  DOI：10.1021/acs.orglett.0c01831

  日期：2020.8.7

  Use of nitromethane as an electrophilic methylene source for the synthesis of symmetrical dithioacetals and bisarylmethanes has been showcased using Sc(OTf)(3) as a catalyst. The procedure allows straightforward access to the densely functionalized dithioacetals and bisarylmethanes under mild conditions. Additionally, the method has been applied for the synthesis of antimalarial tetramethyl mellotojaponin C and anticancer dimeric phloroglucinol derivative.
• Substituted 2-[(2-benzimidazolylsulfinyl)methyl]anilines as potential inhibitors of H+/K+ ATPase
  作者：Gilbert W. Adelstein、Chung H. Yen、Richard A. Haack、Stella Yu、Gary Gullikson、Doreen V. Price、Charles Anglin、Dennis L. Decktor、Henry Tsai、Robert H. Keith

  DOI：10.1021/jm00401a024

  日期：1988.6

  A series of substituted 2-[(2-benzimidazolylsulfinyl)methyl]anilines were synthesized as potential inhibitors of the acid secretory enzyme H+/K+ ATPase. Substitutions on the aniline nitrogen atom resulted in potent enzyme inhibition in vitro but weak activity in gastric fistula dogs. Electron-donating substituents on the aniline ring enhanced in vitro and in vivo potency relative to the unsubstituted analogue. The potency showed a correlation to the calculated pKa of the aniline nitrogen atom. Substitutions on the aniline and benzimidazole rings did not further enhance potency. Di- and trisubstituted aniline derivatives were potent inhibitors of the enzyme system. The preferred combination of substituents were a methoxy group on the benzimidazole ring and a single alkyl group on the aniline ring. One such compound, 76, was an effective inhibitor of acid secretion in the dog and was selected for further pharmacological study.
• Hypervalent Iodine Mediated <i>para</i>-Selective Fluorination of Anilides
  作者：Tian Tian、Wen-He Zhong、Shuai Meng、Xiang-Bao Meng、Zhong-Jun Li

  DOI：10.1021/jo302099d

  日期：2013.1.18

  A metal-free method for the direct regioselective fluorination of anilides has been developed. In the presence of bis(tert-butylcarbonyloxy)iodobenzene (PhI(OPiv)(2)) and hydrogen fluoride-pyridine, the para-fluorination products of anilides were obtained in moderate to good yields. Because of its operational safety and the use of readily available reagents, this new procedure provides facile access to a variety of para-fluorinated anilides.