4-甲氧基-2-(1-萘基)苯甲酰胺 | 108717-14-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 4-甲氧基-2-(1-萘基)苯甲酰胺
• 英文名称: 4-methoxy-N-(naphthalen-2-yl)benzamide
• 英文别名: 4-methoxy-benzoic acid-[2]naphthylamide；4-Methoxy-benzoesaeure-[2]naphthylamid；4-methoxy-N-naphthalen-2-ylbenzamide
• CAS: 108717-14-2
• 化学式: C₁₈H₁₅NO₂
• 分子量: 277.323
• InChiKey: OFVPMKZSPQQCQY-UHFFFAOYSA-N

物化性质

• 沸点：
  395.6±25.0 °C(Predicted)
• 密度：
  1.224±0.06 g/cm3(Predicted)
• 溶解度：
  <0.6 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  4-甲氧基-2-(1-萘基)苯甲酰胺 在 溴 作用下， 生成 3-bromo-4-methoxy-benzoic acid-(1,3,6-tribromo-[2]naphthylamide)
  参考文献：
  名称：

  Phatak; Jadhav, Journal of the Indian Chemical Society, 1959, vol. 36, p. 221

  摘要：

  DOI：
• 作为产物：
  描述：

  大茴香酸 、 2-萘胺 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以60%的产率得到4-甲氧基-2-(1-萘基)苯甲酰胺
  参考文献：
  名称：

  Aryl amide small-molecule inhibitors of microRNA miR-21 function

  摘要：

  MicroRNAs (miRNAs) are single stranded RNA molecules of similar to 22 nucleotides that negatively regulate gene expression. MiRNAs are involved in fundamental cellular processes, such as development, differentiation, proliferation, and survival. MiRNA misregulation has been linked to various human diseases, most notably cancer. MicroRNA-21 (miR-21), a well-established oncomiR, is significantly overexpressed in many types of human cancers, thus rendering miR-21 a potential therapeutic target. Using a luciferase-based reporter assay under the control of miR-21 expression, a high-throughput screen of >300,000 compounds led to the discovery of a new aryl amide class of small-molecule miR-21 inhibitors. Structure-activity relationship (SAR) studies resulted in the development of four aryl amide derivatives as potent and selective miR-21 inhibitors. The intracellular levels of various miRNAs in HeLa cells were analyzed by qRT-PCR revealing specificity for miR-21 inhibition over other miRNAs. Additionally, preliminary mechanism of action studies propose a different mode of action compared to previously reported miR-21 inhibitors, thus affording a new chemical probe for future studies. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.07.016

文献信息

• Oxidation-induced ortho-selective C–H bond functionalization of 2-naphthylamine derivative
  作者：Dongchao Zhang、Zhiliang Huang、Aiwen Lei

  DOI：10.1007/s11426-018-9218-5

  日期：2018.10

  Selective C–H bond functionalization has been emerged as a versatile strategy for the construction of new chemical bonds. In the past decades, the directing group (DG)-assisted C–H bond activation has been developed as one of the most efficient methods for selective C–H functionalization. Although a great progress has been made by utilizing this traditional method, developing new strategy for selective C–H bond functionalization is still highly demanded. Hence, a novel oxidation-induced C–H bond functionalization method was demonstrated in this work. By this new method, ortho-C(sp2)–H chlorination of N-substituted 2-naphthylamine was realized in a highly selective manner.

  选择性 C-H 键官能化已成为构建新化学键的一种多功能策略。在过去的几十年中，定向基团（DG）辅助的 C-H 键活化已被开发为选择性 C-H 功能化最有效的方法之一。尽管利用这种传统方法已经取得了巨大进步，但开发选择性 C-H 键官能化的新策略仍有很大需求。因此，本研究展示了一种新型的氧化诱导 C-H 键官能化方法。通过这种新方法，高选择性地实现了 N-取代的 2-萘胺的正交-C(sp2)-H 氯化。
• Phatak; Jadhav, Journal of the Indian Chemical Society, 1958, vol. 35, p. 717
  作者：Phatak、Jadhav

  DOI：——

  日期：——