2,6-dichloro-N-prop-2-ynylbenzamide | 1137535-37-5

• 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: 2,6-dichloro-N-prop-2-ynylbenzamide
• CAS: 1137535-37-5
• 化学式: C₁₀H₇Cl₂NO
• 分子量: 228.078
• InChiKey: NZVALFKJEBWNAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  2
• 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：

  2,6-dichloro-N-prop-2-ynylbenzamide 在 gold(III) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 30.0h， 以90%的产率得到C₁₀H₇Cl₂NO
  参考文献：
  名称：

  Gold(III) iminophosphorane complexes as catalysts in C–C and C–O bond formations

  摘要：

  The reaction of K[AuCl4] with AgClO4 and iminophosphorane ligands (N, N-IM) Ph3P=NR [R = CH2-2-NC5H4 (1), C(O)-2-NC5H4 (2)] or Ph2PyP=NR [Py = -2-NC5H4; R = Ph (3), C(O) Ph (4)] (mol ratio 1:2.2:1) in acetonitrile affords complexes [AuCl2(N,N-IM)] ClO4 (5-8). These compounds are air- and moisture-stable and they have been evaluated in two types of catalytic processes. They have been found to be effective catalysts in the addition of 2-methylfuran or azulene to methyl vinyl ketone, as well as in the synthesis of 2,5-disubstituted oxazoles from N-propargylcarboxamides. The reactions proceed in mild conditions and with similar yields to those described for AuCl3. Using this method, oxazoles bearing a thiophene functional group 2-(2'-thienyl)-5-methylthiazole can be prepared in excellent yields. In all cases the intermediate 5-methylene-4,5-dihydroxazole can be observed by H-1 NMR. (C) 2008 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2008.09.058
• 作为产物：
  描述：

  2,6-二氯苯甲酰氯 、 炔丙胺 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 2,6-dichloro-N-prop-2-ynylbenzamide
  参考文献：
  名称：

  钯催化级联二氟烷基化/ N-丙炔酰胺的环化：恶唑和恶唑啉的合成

  摘要：

  已经开发了钯催化的方法来构建具有宽泛的官能团耐受性的恶唑和恶唑啉，并且该方法以一锅法将二氟甲基引入杂环中。该系统使用羰基氧作为受体，以添加乙烯基钯中间体以实现环化。恶唑啉衍生物以高立体选择性的Z-异构体形式产生。此外，我们验证了该反应的初步机制。

  DOI：

  10.1021/acs.joc.8b02111

文献信息

• Glycosyl triazoles as novel insect β-N-acetylhexosaminidase OfHex1 inhibitors: Design, synthesis, molecular docking and MD simulations
  作者：Lili Dong、Shengqiang Shen、Wei Chen、Huizhe Lu、Dongdong Xu、Shuhui Jin、Qing Yang、Jianjun Zhang

  DOI：10.1016/j.bmc.2018.11.032

  日期：2019.6

  furnacalis (Guenée) and inhibition of this enzyme has been considered a promising strategy for the development of eco-friendly pesticides. In this article, based on the structure of the catalytic domains of OfHex1, a series of novel glycosyl triazoles were designed and synthesized via Cu-catalyzed azide-alkyne [3+2] cycloaddition reaction. To investigate the potency and selectivity of these glycosyl triazoles

  昆虫酶GH20β-N-乙酰基-d-己糖胺酶OfHex1代表在农业害虫Ostrinia furnacalis（Guenée）中发现的一种重要的几丁质分解酶，对这种酶的抑制被认为是开发环保农药的一种有前途的策略。本文基于OfHex1催化结构域的结构，设计并通过Cu催化的叠氮化物-炔烃[3 + 2]环加成反应合成了一系列新型糖基三唑。为了研究这些糖基三唑的效力和选择性，研究了对OfHex1和HsHexB（人β-N-乙酰基己糖胺酶B）的抑制活性。特别地，化合物17c（OfHex1，Ki ＝28.68μM； HsHexB，Ki＞100μM）显示出对OfHex1的合适的活性和选择性。此外，使用分子对接和MD模拟研究了OfHex1对17c的可能抑制机制。结构-活性关系结果以及形成的结合模式可能为新型OfHex1抑制剂的进一步开发提供有希望的见识。
• Synthesis of Difluoroalkyl Unsaturated β-Amino Acid Derivatives Exclusively through Alkyne Difunctionalization
  作者：Qiang Wang、Jia-Ni Jin、Xi Chen、Xin-Gang Wang、Bo-Sheng Zhang、Jun-Wei Ma、Yong-Min Liang

  DOI：10.1021/acs.joc.8b02440

  日期：2018.12.7

  Alkynes difunctionalization is a powerful strategy in organic synthesis that provides a convenient synthetic entry for internal alkenes. The main challenge in this field was considered to be the geometry control of the newly formed double bond (thermodynamically controlled or kinetically controlled). Herein, we report a novel procedure (through the cyclic compounds broken) to completely control the

  炔烃双官能化是有机合成中的强大策略，可为内部烯烃提供方便的合成入口。该领域的主要挑战被认为是新形成的双键的几何控制（热力学控制或动力学控制）。在本文中，我们报道了一种新颖的方法（通过环状化合物的断裂）来完全控制烯烃的区域选择性。由于氟原子的特殊性质，该产物二氟烷基不饱和β-氨基酸衍生物在一些重要的药物中具有潜在的应用。
• Gold(III) iminophosphorane complexes as catalysts in C–C and C–O bond formations
  作者：David Aguilar、María Contel、Rafael Navarro、Tatiana Soler、Esteban P. Urriolabeitia

  DOI：10.1016/j.jorganchem.2008.09.058

  日期：2009.2

  The reaction of K[AuCl4] with AgClO4 and iminophosphorane ligands (N, N-IM) Ph3P=NR [R = CH2-2-NC5H4 (1), C(O)-2-NC5H4 (2)] or Ph2PyP=NR [Py = -2-NC5H4; R = Ph (3), C(O) Ph (4)] (mol ratio 1:2.2:1) in acetonitrile affords complexes [AuCl2(N,N-IM)] ClO4 (5-8). These compounds are air- and moisture-stable and they have been evaluated in two types of catalytic processes. They have been found to be effective catalysts in the addition of 2-methylfuran or azulene to methyl vinyl ketone, as well as in the synthesis of 2,5-disubstituted oxazoles from N-propargylcarboxamides. The reactions proceed in mild conditions and with similar yields to those described for AuCl3. Using this method, oxazoles bearing a thiophene functional group 2-(2'-thienyl)-5-methylthiazole can be prepared in excellent yields. In all cases the intermediate 5-methylene-4,5-dihydroxazole can be observed by H-1 NMR. (C) 2008 Elsevier B.V. All rights reserved.
• Palladium-Catalyzed Cascade Difluoroalkylation/Cyclization of <i>N</i>-Propargylamides: Synthesis of Oxazoles and Oxazolines
  作者：Jun-Wei Ma、Qiang Wang、Xin-Gang Wang、Yong-Min Liang

  DOI：10.1021/acs.joc.8b02111

  日期：2018.11.2

  A palladium-catalyzed process to construct oxazoles and oxazolines with broad functional-group tolerance has been developed, and the method introduces difluoromethyl groups into heterocycles in a one-pot fashion. This system uses a carbonyl oxygen as the acceptor for the addition of a vinylpalladium intermediate to achieve the cyclization. Oxazoline derivatives are generated as the Z-isomer with high

  已经开发了钯催化的方法来构建具有宽泛的官能团耐受性的恶唑和恶唑啉，并且该方法以一锅法将二氟甲基引入杂环中。该系统使用羰基氧作为受体，以添加乙烯基钯中间体以实现环化。恶唑啉衍生物以高立体选择性的Z-异构体形式产生。此外，我们验证了该反应的初步机制。