N-(2-氯-4-甲基苯基)苯甲酰胺 | 77791-06-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-(2-氯-4-甲基苯基)苯甲酰胺
• 英文名称: N-(2-chloro-4-methylphenyl)benzamide
• 英文别名: benzoic acid-(2-chloro-4-methyl-anilide)；Benzoesaeure-(2-chlor-4-methyl-anilid)；3-Chlor-4-benzamino-toluol
• CAS: 77791-06-1
• 化学式: C₁₄H₁₂ClNO
• mdl: MFCD04562743
• 分子量: 245.708
• InChiKey: PSLRWTDUMOGLKD-UHFFFAOYSA-N

物化性质

• 熔点：
  124-128 °C(Solv: hexane (110-54-3))
• 沸点：
  293.2±33.0 °C(Predicted)
• 密度：
  1.250±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.071
• 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：

  N-(2-氯-4-甲基苯基)苯甲酰胺 在 copper diacetate 、 四甲基乙二胺 作用下， 以 水 为溶剂， 以59%的产率得到6-甲基-2-苯基-1,3-苯并恶唑
  参考文献：
  名称：

  Copper-catalysed intramolecular O-arylation of aryl chlorides and bromides: a straightforward approach to benzo[d]oxazoles in water

  摘要：

  A general, efficient and more sustainable protocol for the copper-catalysed intramolecular O-arylation of o'- haloanilides leading to the benzo[d]oxazole core is reported. Remarkably, the optimised conditions allowed for the use of inexpensive and easily available aryl chlorides as arylating agents. Moreover, all reactions were carried out employing exclusively water as the solvent, rendering the methodology presented herein highly valuable from both environmental and economic points of view. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.08.013
• 作为产物：
  描述：

  苯并-p-甲苯胺 在 亚碘酰苯 、 zinc(II) chloride 作用下， 以 2,2,2-三氟乙醇 为溶剂， 反应 3.0h， 以82%的产率得到N-(2-氯-4-甲基苯基)苯甲酰胺
  参考文献：
  名称：

  ZnCl2/PhI=O Mediated Selective ortho-Chlorination of Amides

  摘要：

  摘要：开发了一种新的由锌(II)和高价碘(III)试剂组成的正氯化体系，用于酰胺的正氯化反应，并以中等至良好的收率（38-85%）获得所需产物。这种高度简便和方便的方法对具有不同取代基的芳香酰胺和烷基酰胺具有耐受性。已经阐明了一个合理的机理，其中包括离子重排和金属盐协助的正氯化反应。

  DOI：

  10.2174/1570178618666210624115748

文献信息

• Amide-assisted radical strategy: metal-free direct fluorination of arenes in aqueous media
  作者：Deqiang Liang、Yanni Li、Shulin Gao、Renlun Li、Xiangguang Li、Baoling Wang、Hai Yang

  DOI：10.1039/c7gc00356k

  日期：——

  A metal- and initiator-free direct fluorination of arenes with the assistance of an amide group is developed. This reaction proceeded under simple aqueous conditions with good functional group tolerance and ortho–para selectivity, and is highly practical because it could be readily scaled up to a multigram-scale. At this stage, an exclusive mechanism could not be proposed, and several possibilities

  在酰胺基团的帮助下，开发了无金属和无引发剂的芳烃直接氟化方法。该反应在简单的水性条件下进行，具有良好的官能团耐受性和邻位-对位选择性，并且非常实用，因为它很容易按比例放大至几克规模。在这一阶段，尚不能提出排他的机制，并且已经讨论了几种可能性。实验和计算研究以及开创性的工作都支持了酰胺辅助的自由基链机理的可能性。
• Palladium-Catalyzed Synthesis of Benzimidazoles and Quinazolinones from Common Precursors
  作者：Jessie E. R. Sadig、Radleigh Foster、Florian Wakenhut、Michael C. Willis

  DOI：10.1021/jo301805d

  日期：2012.11.2

  utilized as complementary precursors for the synthesis of important heterocycles. The synthesis of N-substituted benzimidazoles was possible from the palladium-catalyzed reaction of both classes of substrate with a variety of N-nucleophiles. The use of the imidate precursor for the synthesis of N-substituted quinazolinones by incorporation of a palladium-catalyzed aminocarbonylation reaction has also been

  N-（邻卤代苯基）亚氨基酰氯和相应的酰亚胺化物易于制备，并且可用作合成重要杂环的互补前体。N-取代的苯并咪唑的合成可能是由两类底物与多种N-亲核试剂的钯催化反应所致。还已经证明了亚氨酸酯前体通过掺入钯催化的氨基羰基化反应用于合成N-取代的喹唑啉酮的用途。两种方法都可以耐受各种官能团。
• Revisiting 1-chloro-1,2-benziodoxol-3-one: efficient <i>ortho</i>-chlorination of aryls under aqueous conditions
  作者：Botla Vinayak、Pardhi Vishal Ravindrakumar、Daggupati V. Ramana、Malapaka Chandrasekharam

  DOI：10.1039/c8nj00530c

  日期：——

  The application of 1-chloro-1,2-benziodoxol-3-one as a powerful chlorinating agent as well as oxidant for aniline derivatives is explored. The amide directing group assisted radical mediated ortho-selective chlorination proceeds in the absence of a radical initiator. Various electronically differentiated anilides and sulfonamides are tolerated under aqueous conditions.

  探索了1-氯-1,2-苯并恶唑-3-酮作为强力氯化剂以及苯胺衍生物的氧化剂的应用。在不存在自由基引发剂的情况下，酰胺导向基团辅助的自由基介导的邻位选择性氯化反应进行。在水性条件下可以耐受各种电子分化的苯甲酰胺和磺酰胺。
• Leptin in Children with Newly Diagnosed Type 1 Diabetes: Effect of Insulin Therapy
  作者：Kenneth L. McCormick、Gail J. Mick、Lisa Butterfield、Hugh Ross、Elaine Parton、Joan Totka

  DOI：10.1155/edr.2001.121

  日期：——

  Leptin, the gene product of adipose tissue that signals caloric plentitudeviacentral nervous system receptors, may also have diverse peripheral metabolic actions. Of paramount interest has been the potential interaction(s) between leptin and insulin. Insofar as insulin alters leptin secretion/action (orvice versa), dysregulation of this system could contribute to disease states such as diabetes.

  The purpose of this study was to examine the effect of exogenous insulin on serum leptin in children with newly-diagnosed Type 1 diabetes. Since these patients are hypoinsulinemic (insulindeplet. ed) at diagnosis, they present an ideal opportunity to examine the effect of insulin repletion on serum leptin. Seventeen patients were enrolled. At baseline (prior to insulin therapy), leptin levels were 4.3 ± 1.1ng/ml; they were not statistically related to the baseline serum insulin or illness severity. There was no significant change in serum leptin before, shortly (1–6 days) or several weeks (3–26 weeks) after insulin treatment even when the data was corrected for changes in BMI, hemoglobinA1C, and daily insulin dose. Since repletion of the insulin deficiency that is present in non-acidotic, ambulatory patients with new onset Type 1 diabetes did not alter serum leptin, these results argue against an effect of insulin on serum leptin in the absence of the acute diabetic ketoacidosis. Because as the recuperative months following the diagnosis of new onset Type 1 diabetes are marked by weight gain, the absence of a rise in serum leptin might also indicate either an adaptive (weight permissive) or pathologic (impaired secretory) deficit.

  瘦素是脂肪组织的基因产物，能向中枢神经系统受体发出热量丰度信号，也可能对外周代谢产生多种作用。最令人感兴趣的是瘦素与胰岛素之间的潜在相互作用。只要胰岛素能改变瘦素的分泌/作用（反之亦然），这一系统的失调就可能导致糖尿病等疾病。由于这些患者在确诊时处于低胰岛素血症（胰岛素分泌不足）状态，因此为研究胰岛素补充对血清瘦素的影响提供了一个理想的机会。17 名患者被纳入研究。在基线（胰岛素治疗前），瘦素水平为 4.3 ± 1.1ng/ml ；在统计学上，瘦素水平与基线血清胰岛素或病情严重程度无关。胰岛素治疗前、治疗后不久（1-6 天）或治疗后数周（3-26 周），血清瘦素水平均无明显变化，即使根据体重指数、血红蛋白 A1C 和胰岛素日剂量的变化对数据进行校正也是如此。由于在非酸中毒、非卧床的新发 1 型糖尿病患者体内补充胰岛素不足并不会改变血清瘦素，因此这些结果证明，在没有急性糖尿病酮症酸中毒的情况下，胰岛素不会对血清瘦素产生影响。由于新发 1 型糖尿病患者在确诊后的数月恢复期中体重会增加，因此血清瘦素不升高也可能表明存在适应性（体重许可）或病理性（分泌受损）赤字。
• Substituted p-Aminobenzoic Acids
  作者：Franz Carl Schmelkes、Martin Rubin

  DOI：10.1021/ja01238a006

  日期：1944.10