4-(4-nitrophenoxy)but-1-yn | 191610-38-5

• 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: 4-(4-nitrophenoxy)but-1-yn
• 英文别名: 1-(but-3-yn-1-yloxy)-4-nitrobenzene；1-But-3-ynoxy-4-nitrobenzene
• CAS: 191610-38-5
• 化学式: C₁₀H₉NO₃
• 分子量: 191.186
• InChiKey: WMSWGEAEQMCMME-UHFFFAOYSA-N

物化性质

• 沸点：
  324.8±22.0 °C(Predicted)
• 密度：
  1.205±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(4-nitrophenoxy)but-1-yn 在 N-溴代丁二酰亚胺(NBS) 、 silver nitrate 作用下， 以 丙酮 为溶剂， 以85 %的产率得到
  参考文献：
  名称：

  Oxidant- and Base-Free, Copper-Catalyzed Difluoromethylation of Haloalkynes

  摘要：

  DOI：

  10.1021/acs.orglett.3c03198
• 作为产物：
  描述：

  对硝基苯酚 、 3-丁炔-1-醇 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 甲苯 为溶剂， 反应 24.5h， 以77%的产率得到4-(4-nitrophenoxy)but-1-yn
  参考文献：
  名称：

  Improved Synthesis of C2 and C6 Monoderivatives of α- and β-Cyclodextrin via the Click Chemistry Approach

  摘要：

  An efficient multigram-scale azide-alkyne coupling of cyclodextrin derivatives mono-6-azido-6-deoxy--cyclodextrin, mono-2-O-propargyl--cyclodextrin, and mono-2-O-propargyl--cyclodextrin with terminal alkynyl aryl ethers or azides, mediated by copper(I) is reported. This process uses a stoichiometric ratio of substrates and 5 mol% of the copper catalyst to give the products with full conversion; thus, no chromatographic purification is necessary. The yields of both - and -cyclodextrin derivatives are in the range of 80 to 99%.

  DOI：

  10.1055/s-0034-1380701

文献信息

• Alkene 1,3‐Difluorination via Transient Oxonium Intermediates
  作者：Alice C. Dean、E. Harvey Randle、Andrew J. D. Lacey、Guilherme A. Marczak Giorio、Sayad Doobary、Benjamin D. Cons、Alastair J. J. Lennox

  DOI：10.1002/anie.202404666

  日期：2024.7.22

  diastereoselective hypervalent iodine-mediated 1,3-difluorination of homoallylic (aryl) ethers. The transformation proceeds through a transiently formed oxonium intermediate that is opened by fluoride to rearrange an alkyl chain. The protocol is scalable and tolerates a variety of functional groups and substitution on the alkenyl chain. Mechanistic studies reveal key insights into the reaction selectivity.

  我们报道了高烯丙基（芳基）醚的非对映选择性高价碘介导的 1,3-二氟化。该转化通过瞬时形成的氧鎓中间体进行，该中间体被氟化物打开以重新排列烷基链。该协议具有可扩展性，可容忍烯基链上的各种官能团和取代。机理研究揭示了反应选择性的关键见解。
• Anticancer (hexacarbonyldicobalt)propargyl aryl ethers: Synthesis, antiproliferative activity, apoptosis induction, and effect on cellular oxidative stress
  作者：Sydonie D. Schimler、David J. Hall、Stefan L. Debbert

  DOI：10.1016/j.jinorgbio.2012.10.014

  日期：2013.2

  While an increasing number of (hexacarbonyldicobalt)alkynes have been found to possess antiproliferative activity against a number of cancer cell lines, the role of the organometallic moiety in this bioactivity is not well understood. To gain a better understanding of cobalt's role in the medicinal chemistry of these compounds, several simplified analogs of a known organocobalt anticancer compound were synthesized and assessed for antiproliferative activity against MDA-MB-231 human breast cancer cells. These compounds, mostly (hexacarbonyldicobalt)propargyl aryl ethers, caused 45-93% growth inhibition of that cell line at 40 mu M in a 72 h crystal violet staining assay. The most active analog was the organocobalt nitroaromatic ether 3a, with an IC50 of 3.3 +/- 0.9 mu M. Flow cytometric assays on the same cell line demonstrated that 3a strongly induces apoptosis, arrests the cell cycle at the S phase, increases cellular oxidative stress levels, and induces permeability of the mitochondria! membrane. While the non-cobalt-containing precursor to 3a also caused an increase in mitochondrial membrane permeability, it did not produce an increase in oxidative stress levels, nor did it have apoptosis-inducing or antiproliferative effects. The induction of oxidative stress in the cell may be responsible for some of the antiproliferative activity of compound 3a against this cell line. (C) 2012 Elsevier Inc. All rights reserved.