2-bromo-6-(prop-2-yn-1-yloxy)naphthalene | 20009-46-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-bromo-6-(prop-2-yn-1-yloxy)naphthalene
• 英文别名: 2-bromo-6-prop-2-ynoxynaphthalene
• CAS: 20009-46-5
• 化学式: C₁₃H₉BrO
• mdl: MFCD14631222
• 分子量: 261.118
• InChiKey: PFQJYGYZEXHZJV-UHFFFAOYSA-N

物化性质

• 沸点：
  371.7±22.0 °C(Predicted)
• 密度：
  1.446±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.076
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-bromo-6-(prop-2-yn-1-yloxy)naphthalene 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 二苯基二硒醚 、 双氧水 、 三乙胺 作用下， 以 水 、 乙腈 为溶剂， 反应 1.17h， 生成 8-bromo-1-phenylnaphtho[2,1-b]furan-2-carbaldehyde
  参考文献：
  名称：

  丙二醇芳基醚的二苯二硒化物介导的Domino Claisen型重排/环化：萘呋喃-2-羧醛衍生物的合成。

  摘要：

  在无金属条件下开发了炔丙基芳基醚的二苯基-二硒化物介导的克莱森型重排/环化反应，以中等至极好的收率提供了各种萘呋喃-2-甲醛。广泛的底物范围和出色的官能团相容性表明，它可以是一种以高度区域选择性的方式访问萘呋喃-2-甲醛的简单有效的方法。此外，该反应可以按比例放大至克级。

  DOI：

  10.1021/acs.orglett.9b02942
• 作为产物：
  描述：

  6-溴-2-萘酚 、 3-溴丙炔 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-bromo-6-(prop-2-yn-1-yloxy)naphthalene
  参考文献：
  名称：

  用于合成磺化 2H-色烯衍生物的失活炔烃的电化学氧化环化

  摘要：

  已实现失活的炔丙基芳基醚与磺酰肼的独特、简便且直接的电化学氧化环化，从而生成 3-磺化 2 H-色烯。值得注意的是，该协议涉及一种绿色方法，该方法在温和的反应条件下工作，在未分割的电池中使用恒定电流，并且没有氧化剂和催化剂。值得注意的是，该过程表现出广泛的范围和官能团耐受性以提供 2 H -色烯，并且将代表与传统色烯合成相比的替代和可持续战略。

  DOI：

  10.1021/acs.orglett.3c00691

文献信息

• 4-Deoxy-4-fluoro-xyloside derivatives as inhibitors of glycosaminoglycan biosynthesis
  作者：Yasuhiro Tsuzuki、Thao Kim Nu Nguyen、Dinesh R. Garud、Balagurunathan Kuberan、Mamoru Koketsu

  DOI：10.1016/j.bmcl.2010.10.085

  日期：2010.12

  click chemistry for evaluating their potential utility as inhibitors of glycosaminoglycan biosynthesis. 2,3-Di-O-benzoyl-4-deoxy-4-fluoro-β-d-xylopyranosylazide, obtained from l-arabinopyranose by six steps, was treated with a wide variety of azide-reactive triple bond-containing hydrophobic agents in the presence of Cu2+ salt/ascorbic acid, a step known as click chemistry. After click chemistry, benzoylated

  使用点击化学制备了各种 4-脱氧-4-氟-木糖苷，以评估它们作为糖胺聚糖生物合成抑制剂的潜在效用。2,3- Di - O - benzoyl -4-deoxy-4-fluoro-β- d - xylopyranosylazide，通过六步从l-阿拉伯吡喃糖中获得，在Cu 2+的存在盐/抗坏血酸，这一步骤称为点击化学。单击化学后，苯甲酰化衍生物在 Zemplén 条件下脱保护以获得 4-脱氧-4-氟-木糖苷衍生物。然后使用 HPLC 在反相 C18 柱上分离 12 种衍生物的 α:β-异构体混合物，并评估所得 24 种 4-脱氧-4-氟-木糖苷抑制内皮细胞中糖胺聚糖生物合成的能力。我们确定了两种木糖苷衍生物，它们选择性地抑制硫酸乙酰肝素和硫酸软骨素/硫酸德曼生物合成而不影响细胞活力。这些新型衍生物可潜在地用于定义蛋白聚糖在模型生物中的生物学作用，也可用作治疗糖胺聚糖参与的各种人类疾病的治疗剂。
• Silica immobilized copper N‐heterocyclic carbene: An effective route to 1,2,3‐triazoles via azide‐alkyne cycloaddition and multicomponent click reaction
  作者：Anirban Garg、Nobomi Borah、Jasmin Sultana、Akshay Kulshrestha、Arvind Kumar、Diganta Sarma

  DOI：10.1002/aoc.6298

  日期：2021.9

  supported copper N-heterocyclic carbene (Cu-NHC@SiO2) complex is prepared and characterized by scanning electron microscopy (SEM), energy dispersive X-ray spectroscopy (EDX) and X-ray photoelectron spectroscopy (XPS) analyses. This complex is an efficient and easily retrievable catalyst for 1,2,3-triazole synthesis through direct azide-alkyne cycloaddition reaction as well as one-pot reaction using arylboronic

  制备了一种新型二氧化硅负载的铜 N-杂环卡宾 (Cu-NHC@SiO 2 ) 配合物，并通过扫描电子显微镜 (SEM)、能量色散 X 射线光谱 (EDX) 和 X 射线光电子能谱 (XPS) 分析表征。该配合物是一种有效且易于回收的催化剂，用于通过直接叠氮化物-炔烃环加成反应以及使用芳基硼酸的一锅反应合成 1,2,3-三唑。该催化体系也适用于从各种苯甲醛合成 4-芳基-NH-1,2,3-三唑。此外，对于通过直接叠氮化物-炔烃环加成和多组分反应合成 1,2,3-三唑的所有三种方法，催化剂可以有效地循环至第五次循环。
• Synthesis and evaluation of naphthyl bearing 1,2,3-triazole analogs as antiplasmodial agents, cytotoxicity and docking studies
  作者：Saikrishna Balabadra、MeenaKumari Kotni、Vijjulatha Manga、Aparna Devi Allanki、Rajesh Prasad、Puran Singh Sijwali

  DOI：10.1016/j.bmc.2016.10.029

  日期：2017.1

  Novel series of naphthyl bearing 1,2,3-triazoles (4a-t) were synthesized and evaluated for their in vitro antiplasmodial activity against pyrimethamine (Pyr)-sensitive and resistant strains of Plasmodium falciparum. The synthesized compounds were assessed for their cytotoxicity employing human embryonic kidney cell line (HEK-293), and none of them was found to be toxic. Among them 4j, 4k, 4l, 4m, 4n, 4t exhibited significant antiplasmodial activity in both strains, of which compounds 4m, 4n and 4t (similar to 3.0fold) displayed superior activity to Pyr against resistant strain. Pyr and selected compounds (4n, 4p and 4t) that repressed parasite development also inhibited PfDHFR activity of the soluble parasite extract, suggesting that anti-parasitic activity of these compounds is a result of inhibition of the parasite DHFR. In silico studies suggest that activity of these compounds might be enhanced due to p-p stacking. (C) 2016 Elsevier Ltd. All rights reserved.
• Synthesis and Bioactivities Evaluation of Novel N-Pyridylpyrazole Derivatives with 1,2,3-Triazole and Quinazolin-4(3H)-one Substructures
  作者：Yunyun Zhou、Zhengming Li、Wei Wei、Liangliang Zhu

  DOI：10.3987/com-18-13944

  日期：——

  Two series of N-pyridylpyrazole derivatives containing 1,2,3-triazole and quinazolin-4(3H)-one substructures were designed and synthesized. In total, 18 novel compounds were prepared, and all compounds were characterized by H-1 NMR, C-13 NMR and elemental analysis (EA). Preliminary bioassay results revealed that a few of new compounds with quinazolin-4(3H)-one moiety exhibited good insecticidal activity against the oriental armyworm (Mythimna separata). In addition, the compounds Ia-h with 1, 2, 3-triazole moiety showed broad-spectrum antifungal activities against Fusarium oxysporum f.sp.cucumerinum, Cercospora arachidicola Hori, Botryosphaeria dothidea, Alternaria solani, Gibberella zeae and Phytophthora capsici at 50 [mu g/mL concentration. The EC50 values of Ib and If against Botryosphaeria dothidea were 13.9 and 11.0 mu g/mL, respectively, which were comparable to Chlorothalonil. These results indicated the potential application of N-pyridylpyrazole derivatives as fungicide in further study.
• SYNTHESIS OF NOVEL XYLOSIDES AND POTENTIAL USES THEREOF
  申请人：Balagurunathan Kuberan

  公开号：US20100143980A1

  公开（公告）日：2010-06-10

  The present invention includes a xyloside for use in inducing synthesis of a glycosaminoglycan in a cell, the xyloside having a chemical structure of one of Formula (1), Formula (2), Formula (3), Formula (4), Formula (5), Formula (6), Formula (7), Formula (8), Formula (9), or Formula (10) as shown herein. Also, the present invention includes a method of making a xyloside for use in inducing synthesis of a glycosaminoglycan in a cell, wherein the method is performed with “Click” chemistry. Additionally, the present invention includes a method of administering a xyloside so as to induce synthesis of a glycosaminoglycan in a cell.