2-chloro-N-(4-ethynylphenyl)acetamide | 1233382-40-5

• 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-(4-ethynylphenyl)acetamide
• CAS: 1233382-40-5
• 化学式: C₁₀H₈ClNO
• 分子量: 193.633
• InChiKey: DRMCPPQLVNCYAC-UHFFFAOYSA-N

物化性质

• 沸点：
  365.3±27.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 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-chloro-N-(4-ethynylphenyl)acetamide 、 4-cyclopropyl-5-pyridin-3-yl-2,4-dihydro-[1,2,4]triazole-3-thione 在 caesium carbonate 作用下， 以 乙腈 为溶剂， 反应 16.0h， 生成
  参考文献：
  名称：

  Narrow SAR in odorant sensing Orco receptor agonists

  摘要：

  The systematic exploration of a series of triazole-based agonists of the cation channel insect odorant receptor is reported. The structure-activity relationships of independent sections of the molecules are examined. Very small changes to the compound structure were found to exert a large impact on compound activity. Optimal substitutions were combined using a 'mix-and-match' strategy to produce best-in-class compounds that are capable of potently agonizing odorant receptor activity and may form the basis for the identification of a new mode of insect behavior modification. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.04.081
• 作为产物：
  描述：

  4-乙炔基苯胺 、 氯乙酰氯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以72%的产率得到2-chloro-N-(4-ethynylphenyl)acetamide
  参考文献：
  名称：

  A click chemistry approach to C3 symmetric, G-quadruplex stabilising ligands

  摘要：

  描述了利用铜催化的叠氮化物-炔“点击”反应，基于结构的设计和合成一系列三三唑G-四联体结合配体。报告并讨论了配体稳定 G-四链体的结果。

  DOI：

  10.1039/c005055e

文献信息

• A click chemistry approach to C3 symmetric, G-quadruplex stabilising ligands
  作者：John E. Moses、Dougal J. Ritson、Fengzhi Zhang、Caterina Maria Lombardo、Shozeb Haider、Neil Oldham、Stephen Neidle

  DOI：10.1039/c005055e

  日期：——

  Described is the structure-based design and synthesis of a series of tris-triazole G-quadruplex binding ligands utilising the copper catalysed azide–alkyne ‘click’ reaction. The results of G-quadruplex stabilisation by the ligands are reported and discussed.

  描述了利用铜催化的叠氮化物-炔“点击”反应，基于结构的设计和合成一系列三三唑G-四联体结合配体。报告并讨论了配体稳定 G-四链体的结果。
• Sulfamate Acetamides as Self-Immolative Electrophiles for Covalent Ligand-Directed Release Chemistry
  作者：Rambabu N. Reddi、Adi Rogel、Ronen Gabizon、Dattatraya Gautam Rawale、Battu Harish、Shir Marom、Barr Tivon、Yamit Shorer Arbel、Neta Gurwicz、Roni Oren、Keren David、Jingjing Liu、Shirly Duberstein、Maxim Itkin、Sergey Malitsky、Haim Barr、Ben-Zion Katz、Yair Herishanu、Idit Shachar、Ziv Shulman、Nir London

  DOI：10.1021/jacs.2c08853

  日期：2023.2.15

  Electrophiles for covalent inhibitors that are suitable for in vivo administration are rare. While acrylamides are prevalent in FDA-approved covalent drugs, chloroacetamides are considered too reactive for such purposes. We report sulfamate-based electrophiles that maintain chloroacetamide-like geometry with tunable reactivity. In the context of the BTK inhibitor ibrutinib, sulfamate analogues showed

  适合体内给药的共价抑制剂的亲电子试剂很少。虽然丙烯酰胺在 FDA 批准的共价药物中很常见，但氯乙酰胺被认为对于此类目的反应性太强。我们报道了基于氨基磺酸盐的亲电子试剂，其保持类似氯乙酰胺的几何形状并具有可调节的反应性。在 BTK 抑制剂依鲁替尼的背景下，氨基磺酸类似物在蛋白质标记、体外和细胞激酶活性测定中显示出较低的反应性和相当的效力，并且在 CLL 小鼠模型中有效。在第二个示例中，我们将氯乙酰胺 Pin1 抑制剂转化为有效的选择性氨基磺酸乙酰胺，并提高了缓冲液稳定性。最后，我们证明氨基磺酸乙酰胺可用于共价配体定向释放（CoLDR）化学，既可用于生成“开启”探针，也可用于蛋白质的无痕配体定向位点特异性标记。总而言之，这种化学物质代表了适合体内共价靶向的亲电试剂列表中的一个有前景的新成员。
• Narrow SAR in odorant sensing Orco receptor agonists
  作者：Ian M. Romaine、Robert W. Taylor、Samsudeen P. Saidu、Kwangho Kim、Gary A. Sulikowski、Laurence J. Zwiebel、Alex G. Waterson

  DOI：10.1016/j.bmcl.2014.04.081

  日期：2014.6

  The systematic exploration of a series of triazole-based agonists of the cation channel insect odorant receptor is reported. The structure-activity relationships of independent sections of the molecules are examined. Very small changes to the compound structure were found to exert a large impact on compound activity. Optimal substitutions were combined using a 'mix-and-match' strategy to produce best-in-class compounds that are capable of potently agonizing odorant receptor activity and may form the basis for the identification of a new mode of insect behavior modification. (C) 2014 Elsevier Ltd. All rights reserved.