1,3-二(2-丙炔氧基)苯 | 26627-36-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 1,3-二(2-丙炔氧基)苯
• 英文名称: m-bis(propargyloxy)benzene
• 英文别名: 1,3-bis(prop-2-yn-1-yloxy)benzene；1,3-bis(prop-2-ynyloxy)benzene；1,3-bis(2-propynyloxy)benzene；1,3-bis(prop-2-ynoxy)benzene
• CAS: 26627-36-1
• 化学式: C₁₂H₁₀O₂
• 分子量: 186.21
• InChiKey: HSRDPYWXTZGWFQ-UHFFFAOYSA-N

物化性质

• 熔点：
  38.0 to 42.0 °C
• 沸点：
  302.2±32.0 °C(Predicted)
• 密度：
  1.088±0.06 g/cm3(Predicted)
• 最大波长(λmax)：
  295nm(H2O)(lit.)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  0-10°C

反应信息

• 作为反应物：
  描述：

  1,3-二(2-丙炔氧基)苯 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  对映选择性钯催化的艾伦与氧化膦的氢膦酰化：获得手性烯丙基氧化膦

  摘要：

  通过钯催化的丙二烯与氧化膦的不对称氢膦酰化，证明了一种高效、通用和原子经济的手性烯丙基氧化膦方案。以高产率（高达 99%）和对映选择性（高达 99% ee）获得了一系列具有多种官能团的手性烯丙基氧化膦。

  DOI：

  10.1002/anie.202112285
• 作为产物：
  描述：

  间苯二酚 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成 1,3-二(2-丙炔氧基)苯
  参考文献：
  名称：

  Synthesis and Bioactivities Evaluation of Novel N-Pyridylpyrazole Derivatives with 1,2,3-Triazole and Quinazolin-4(3H)-one Substructures

  摘要：

  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.

  DOI：

  10.3987/com-18-13944

文献信息

• Cholesterol appended bis-1,2,3-triazoles as simple supramolecular gelators for the naked eye detection of Ag⁺, Cu²⁺ and Hg²⁺ ions
  作者：Kumaresh Ghosh、Atanu Panja、Santanu Panja

  DOI：10.1039/c5nj02771c

  日期：——

  Cholesterol coupled bis-1,2,3-triazoles have been designed and synthesized. Their gelation abilities and cation responsive behaviors are documented.

  胆固醇偶联的双-1,2,3-三唑已被设计并合成。它们的凝胶能力和阳离子响应行为已记录。
• Efficient Multicomponent Synthesis of Mono-, Bis-, and Tris-1,2,3-triazoles Supported by Hydroxybenzene Scaffolds
  作者：Guillermo Negrón-Silva、Daniel Mendoza-Espinosa、Leticia Lomas-Romero、Atilano Gutiérrez-Carrillo、Delia Soto-Castro

  DOI：10.1055/s-0033-1339376

  日期：——

  present methodology could be useful for the building up of multi-triazole libraries easily tunable with donor or attractor functional groups. A versatile one-pot synthesis of a series of mono-, bis- and tris-1,2,3-triazoles supported by commercially available hydroxybenzene scaffolds has been developed employing click chemistry. The multicomponent copper(I)-catalyzed 1,3-dipolar cycloaddition of sodium azide

  摘要 利用点击化学，已经开发了一种通用的一锅法合成的一系列由市售羟苯支架支撑的单，双和三，1,2-3-三唑。多组分铜（I）催化的叠氮化钠，炔丙基溴和对位取代的苄基衍生物的1,3-偶极环加成反应生成N-具有几个给电子或吸电子基团的苄基官能化三唑。尽管制备了高度取代的分子，但提供良好收率的反应条件包括室温，在16至24小时之间振荡的时间以及5-10 mol％的催化剂负载量。本方法学对于建立容易与供体或吸引子官能团调节的多三唑库可能是有用的。 利用点击化学，已经开发了一种通用的一锅法合成的一系列由市售羟苯支架支撑的单，双和三，1,2-3-三唑。多组分铜（I）催化的叠氮化钠，炔丙基溴和对位取代的苄基衍生物的1,3-偶极环加成反应生成N-具有几个给电子或吸电子基团的苄基官能化三唑。尽管制备了高度取代的分子，但提供良好收率的反应条件包括室温，在16至24小时之间振荡的时间以及5-10 mol％的催化剂
• A programmable “build–couple” approach to the synthesis of heterofunctionalized polyvalent molecules
  作者：Ritwik Burai、Jaruwan Chatwichien、Brian R. McNaughton

  DOI：10.1039/c1ob05606a

  日期：——

  A maximally divergent “build–couple” synthesis of heterofunctionalized polyvalent molecules is described. This strategic approach enables the synthesis of highly diverse polyvalent structures from a pre-programmed combinatorial set of modules.

  描述了一种最大化差异性的“构建–耦合”合成方法，用于制备异功能化的多价分子。这种策略性方法使得从预设的模块组合集中合成高度多样化的多价结构成为可能。
• Antiviral Activity of 1,4-Disubstituted-1,2,3-Triazoles against HSV-1 <i>in vitro</i>
  作者：Daiane J Viegas、Verônica D da Silva、Camilla D Buarque、David C Bloom、Paula A Abreu

  DOI：10.3851/imp3387

  日期：2020.11

  Herpes simplex virus 1 (HSV-1) affects a large part of the adult population. Anti-HSV-1 drugs, such as acyclovir, target thymidine kinase and viral DNA polymerase. However, the emerging of resistance of HSV-1 alerts for the urgency in developing new antivirals with other therapeutic targets. Thus, this study evaluated a series of 1,4-disubstituted-1,2,3-triazole derivatives against HSV-1 acute infection and provided deeper insights into the possible mechanisms of action.

  Human fibroblast cells (HFL-1) were infected with HSV-1 17 syn+ and treated with the triazole compounds at 50 μM for 24 h. The 50% effective drug concentration (EC₅₀) was determined for the active compounds. Their cytotoxicity was also evaluated in HFL-1 with the 50% cytotoxic concentration (CC₅₀) determined using CellTiter-Glo^® solution. The most promising compounds were evaluated by virucidal activity and influence on virus egress, DNA replication and transcription, and effect on an acyclovir-resistant HSV-1 strain.

  Compounds 3 ( (E)-4-methyl-N′-(2-(4-(phenoxymethyl)-1H-1,2,3-triazol1yl)benzylidene)benzenesulfonohydrazide) and 4 ( 2,2′-(4,4′-((1,3-phenylenebis(oxy))bis(methylene))bis(1H-1,2,3-triazole-4,1 diyl)) dibenzaldehyde) were the most promising, with an EC₅₀ of 16 and 21 μM and CC₅₀ of 285 and 2,593 μM, respectively. Compound 3 was able to inhibit acyclovir-resistant strain replication and to interfere with virus egress. Both compounds did not affect viral DNA replication, but inhibited significantly the expression of ICP0, ICP4 and gC. Compound 4 also affected the transcription of UL30 and ICP34.5.

  Our findings demonstrated that these compounds are promising antiviral candidates with different mechanisms of action from acyclovir and further studies are merited.

  背景 单纯疱疹病毒 1（HSV-1）影响着大部分成年人。阿昔洛韦等抗 HSV-1 药物以胸苷激酶和病毒 DNA 聚合酶为靶点。然而，HSV-1 新出现的耐药性提醒人们迫切需要开发具有其他治疗靶点的新型抗病毒药物。因此，本研究评估了一系列 1,4-二取代-1,2,3-三唑衍生物对 HSV-1 急性感染的作用，并深入探讨了其可能的作用机制。方法 用人成纤维细胞（HFL-1）感染 HSV-1 17 syn+，并用 50 μM 的三唑化合物处理 24 小时。还在 HFL-1 中评估了这些化合物的细胞毒性，使用 CellTiter-Glo® 溶液测定了 50%的细胞毒性浓度（CC50）。根据杀病毒活性、对病毒排出、DNA 复制和转录的影响以及对耐阿昔洛韦 HSV-1 株系的影响，对最有希望的化合物进行了评估。结果 化合物 3（(E)-4-甲基-N′-(2-(4-(苯氧基甲基)-1H-1,2,3-三唑1基)苯亚甲基)苯磺酰肼）和 4（2,2′-(4,4′-(1、2,2′-(4,4′-((1,3-苯基双(氧基))双(亚甲基))双(1H-1,2,3-三唑-4,1 二基))二苯甲醛)最有前途，其 EC50 值分别为 16 和 21 μM，CC50 值分别为 285 和 2,593 μM。化合物 3 能够抑制耐阿昔洛韦毒株的复制，并干扰病毒的排出。这两种化合物都不影响病毒 DNA 的复制，但能显著抑制 ICP0、ICP4 和 gC 的表达。化合物 4 还影响 UL30 和 ICP34.5 的转录。结论 我们的研究结果表明，这些化合物是很有希望的抗病毒候选化合物，其作用机制与阿昔洛韦不同，值得进一步研究。
• Photocatalytic Oxidative Bromination of Electron-Rich Arenes and Heteroarenes by Anthraquinone
  作者：Daniel Petzold、Burkhard König

  DOI：10.1002/adsc.201701276

  日期：2018.2.15

  The estimated excited oxidation potential of sodium anthraquinone‐2‐sulfonate (SAS) increases from 1.8 V to about 2.3 V vs SCE by protonation with Brønsted acids. This increased photooxidation power of protonated anthraquinone was used for the regio‐selective oxidative bromination of electron rich (hetero)arenes and drugs in good yield. The mild reaction conditions are compatible with many functional

  通过布朗斯台德酸的质子化，蒽醌-2-磺酸钠（SAS）的估计激发氧化电势相对于SCE从1.8 V增加到约2.3V。质子化蒽醌提高的光氧化能力可用于富电子（杂）芳烃和药物的区域选择性氧化溴化，收率很好。温和的反应条件与许多官能团兼容，例如双键和三键，酮，酰胺和胺，羟基，羧酸和氨基甲酸酯。机理研究表明，芳烃的光氧化反应继之以亲核性溴化物添加是可能的途径。