2-(2-氯苯氧基)乙酰氨 | 35368-68-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 2-(2-氯苯氧基)乙酰氨
• 中文别名: 2-(2-氯苯氧基)乙酰胺
• 英文名称: 2-(2-chlorophenoxy)acetamide
• 英文别名: -acetamid；<2-Chlor-phenoxy>-acetamid；(2-chloro-phenoxy)-acetic acid amide；(2-Chlor-phenoxy)-essigsaeure-amid；2-chlorophenoxyacetamide；o-chlorophenoxyacetamide
• CAS: 35368-68-4
• 化学式: C₈H₈ClNO₂
• mdl: MFCD00173819
• 分子量: 185.61
• InChiKey: VFUNLXYSSCTXBG-UHFFFAOYSA-N

物化性质

• 熔点：
  149-150 °C
• 沸点：
  370.8±22.0 °C(Predicted)
• 密度：
  1.300±0.06 g/cm3(Predicted)
• 稳定性/保质期：
  常规情况下不会分解，没有危险反应。<?xml:namespace prefix = o ns = "urn:schemas-microsoft-com:office:office" />

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2924299090
• 储存条件：
  密封保存于阴凉干燥处

反应信息

• 作为反应物：
  描述：

  2-(2-氯苯氧基)乙酰氨 在 sodium hydroxide 作用下， 生成 邻氯苯氧乙酸
  参考文献：
  名称：

  Leaper; Bishop, Botanical Gazette, 1951, vol. 112, p. 250,252, 253

  摘要：

  DOI：
• 作为产物：
  描述：

  邻氯苯氧乙酸 在 氯化亚砜 作用下， 生成 2-(2-氯苯氧基)乙酰氨
  参考文献：
  名称：

  Minton; Stephen, Journal of the Chemical Society, 1922, vol. 121, p. 1603

  摘要：

  DOI：

文献信息

• Synthesis and Biological Evaluation of 2-Phenoxyacetamide Analogues, a Novel Class of Potent and Selective Monoamine Oxidase Inhibitors
  作者：Wei Shen、Shian Yu、Jiaming Zhang、Weizheng Jia、Qing Zhu

  DOI：10.3390/molecules191118620

  日期：——

  Monoamine oxidases (EC 1.4.3.4; MAOs), a family of FAD-containing enzymes, is an important target for antidepressant drugs. In this paper, a series of 2-phenoxyacetamide analogues were synthesized, and their inhibitory potency towards monoamine oxidases A (MAO-A) and B (MAO-B) were evaluated using enzyme and cancer cell lysate. 2-(4-Methoxyphenoxy)acetamide (compound 12) (SI = 245) and (2-(4-((prop-2-ynylimino)methyl)phenoxy)acetamide (compound 21) (IC50MAO-A = 0.018 μM, IC50MAO-B = 0.07 μM) were successfully identified as the most specific MAO-A inhibitor, and the most potent MAO-A/-B inhibitor, respectively. The inhibitory activities of these two compounds in living cells were also further evaluated utilizing HepG2 and SHSY-5Y cell lysates.

  单胺氧化酶（EC 1.4.3.4；MAOs）是一类含有FAD的酶，是抗抑郁药物的重要靶点。本文中，合成了一系列2-苯氧乙酰胺类似物，并使用酶和癌细胞裂解液评估了它们对单胺氧化酶A（MAO-A）和B（MAO-B）的抑制活性。成功鉴定出2-（4-甲氧基苯氧基）乙酰胺（化合物12）（SI = 245）和2-（4-（（丙-2-炔基亚氨基）甲基）苯氧基）乙酰胺（化合物21）（IC50MAO-A = 0.018 μM，IC50MAO-B = 0.07 μM）分别作为最特异的MAO-A抑制剂和最强的MAO-A/-B抑制剂。还利用HepG2和SHSY-5Y细胞裂解液进一步评估了这两种化合物在活细胞中的抑制活性。
• 1,3-Disubstituted 4-methyl-1H-pyrrole-2-carboxamides and their Use in Medicaments
  申请人：Oberboersch Stefan

  公开号：US20090137573A1

  公开（公告）日：2009-05-28

  1,3-disubstituted 4-methyl-1H-pyrrole-2-carboxamides corresponding to formula I methods for their production, pharmaceutical compositions containing them, and the use thereof for noradrenalin receptor regulation, particularly for inhibiting noradrenalin reuptake, and/or for 5-HT receptor regulation, particularly for inhibiting 5-hydroxy tryptophan reuptake, and/or for opioid receptor regulation and/or for batrachotoxin (BTX) receptor regulation and/or for treating or inhibiting pain and other conditions.

  1,3-二取代的4-甲基-1H-吡咯-2-甲酰胺对应于公式I，其制备方法，含有它们的药物组合物，以及用于去甲肾上腺素受体调节的用途，特别是用于抑制去甲肾上腺素再摄取，和/或用于5-HT受体调节，特别是用于抑制5-羟色氨酸再摄取，和/或用于阿片受体调节和/或用于蟾毒素（BTX）受体调节和/或用于治疗或抑制疼痛和其他病况。
• Efficient synthesis of benzene-fused 6/7-membered amides via Xphos Pd G2 catalyzed intramolecular C–N bond formation
  作者：Zhou Xu、Ke Li、Rongliang Zhai、Ting Liang、Xiaodie Gui、Rongli Zhang

  DOI：10.1039/c7ra09160e

  日期：——

  6/7-membered amides via intramolecular amidation of aryl chlorides catalyzed by a Buchwald–Hartwig second generation Pd catalyst (Xphos Pd G2) has been successfully developed. This catalyst system allows the primary amides which have only modest nucleophilicity to be coupled successfully even with electron rich aryl chlorides in short reaction time. The intramolecular amidation reaction also has good

  对苯稠6/7元酰胺一种有效的方法通过由一个布赫瓦尔德-哈特维希第二代催化剂的Pd（钯XPHOS G2）催化的芳基氯的分子内酰胺化已研制成功。该催化剂体系使得仅具有适度亲核性的伯酰胺即使在短的反应时间内也能与富电子的芳基氯化物成功地偶联。分子内酰胺化反应还具有良好的化学选择性和优异的官能团相容性。
• Synthesis of aryloxyacetylthiourea derivatives for the development of radicle elongation inhibitor of parasitic weeds
  作者：Motohiro Sonoda、Yusuke Mimura、Shizuki Noda、Atsushi Okazawa

  DOI：10.1016/j.tet.2023.133333

  日期：2023.4

  yl)thiourea (PI-28), has attracted attention as a lead compound for the development of radicle elongation inhibitors in Orobanche minor seeds germination. In this study, we synthesized PI-28 and its derivatives in two steps using commercially available phenols, 2-chloroacetamide, and N-aryl isothiocyanates. In this method, 2-aryloxyacetanilides, which are also attractive as bioactive compounds, were

  芳氧基乙酰基硫脲，1-(3,4-二氯苯基)-3-(2-苯氧基乙酰基)硫脲 (PI-28) 作为先导化合物引起了人们的关注，该化合物用于开发列班列小种子萌发中的胚根伸长抑制剂。在这项研究中，我们使用市售的酚类、2-氯乙酰胺和N分两步合成了 PI-28 及其衍生物-芳基异硫氰酸酯。在该方法中，获得作为生物活性化合物也很有吸引力的 2-芳氧基乙酰苯胺作为副产物。根据对照实验的结果，副产物的形成是由于在反应过程中另一种芳基异硫氰酸酯的作用导致形成的芳酰氧基乙酰硫脲中异硫氰酸酯部分的损失。此外，我们还开发了一种 PI-28 衍生物的一锅法合成方法，总收率相当。
• Synthesis of aryloxyacetamides from arylboronic acids and 2-bromoacetonitrile promoted by alkaline solutions of hydrogen peroxide
  作者：Mengping Guo、Yingmin Li、Yongju Wen、Xiuli Shen

  DOI：10.1039/d2ra07451f

  日期：——

  A novel and metal catalyst-free synthesis of aryloxyacetamides from the corresponding arylboronic acids and 2-bromoacetonitrile promoted by alkaline solutions of hydrogen peroxide has been developed involving an oxidation-reduction of eco-friendly H2O2 with simultaneous reaction ipso-hydroxylation of arylboronic acid and hydration of the nitrile. This protocol is compatible with sensitive substituents

  开发了一种由相应的芳基硼酸和 2-溴乙腈在过氧化氢碱性溶液促进下合成芳氧基乙酰胺的新型无金属催化剂合成方法，涉及环保型 H2O2 的氧化还原反应以及芳基硼酸的同羟基化反应和水合反应腈。该协议与连接到芳基硼酸的敏感取代基兼容，并在纯水中以中等到良好的收率提供所需的产品。