3-呋喃-2-苯甲酸甲酯 | 207845-31-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-呋喃-2-苯甲酸甲酯
• 英文名称: methyl 3-(furan-2-yl)benzoate
• CAS: 207845-31-6
• 化学式: C₁₂H₁₀O₃
• mdl: MFCD05022490
• 分子量: 202.21
• InChiKey: JIFLATATBSNBKH-UHFFFAOYSA-N

物化性质

• 沸点：
  318.0±25.0 °C(Predicted)
• 密度：
  1.152±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.083
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2932190090

反应信息

• 作为反应物：
  描述：

  3-呋喃-2-苯甲酸甲酯 在 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 24.0h， 以80%的产率得到3-(2-呋喃基)苯甲酸
  参考文献：
  名称：

  Synthesis and activity of isoleucine sulfonamide derivatives as novel botulinum neurotoxin serotype A light chain inhibitors

  摘要：

  The botulinum neurotoxin (BoNT) is the most lethal protein known to man causing the deadly disease botulinum. The neurotoxin, composed of a heavy (HC) and light (LC) chain, work in concert to cause muscle paralysis. A therapeutic strategy to treat individuals infected with the neurotoxin is inhibiting the catalytic activity of the BoNT LC. We report the synthesis, inhibition study and computational docking analysis of novel small molecule BoNT/A LC inhibitors. A structure activity relationship study resulted in the discovery of D-isoleucine functionalized with a hydroxamic acid on the C-terminal and a biphenyl with chlorine at C- 2 connected by a sulfonamide linker at the N-terminus. This compound has a measured IC50 of 0.587 mu M for the BoNT/A LC. Computational docking analysis indicates the sulfonamide linker adopts a geometry that is advantageous for binding to the BoNT LC active site. In addition, Arg363 is predicted to be involved in key binding interactions with the scaffold in this study.

  DOI：

  10.1016/j.bmc.2020.115659
• 作为产物：
  描述：

  甲醇 、 3-(2-呋喃基)苯甲酸 在 硫酸 作用下， 反应 48.0h， 生成 3-呋喃-2-苯甲酸甲酯
  参考文献：
  名称：

  鉴定 邻位（+）-ESI高分辨率质谱中气相相邻基团参与效应的取代苯甲酸/酯衍生物

  摘要：

  苯甲酸/酯/酰胺衍生物是药物化合物中的常见部分，并且通过传统的串联质谱分析对位置异构体鉴定提出了挑战。提出了一种利用气相邻近基团参与（NGP）效应以高分辨率质谱（HRMS 1）区分邻位取代的苯甲酸/酯衍生物的方法。对于邻位取代的亲核基团，观察到明显的水/醇损失（在MS 1光谱中> 30％的丰度）；这些片段的峰对于相应的对位和元不可见-取代的类似物。实验还扩展到了suvorexant（Belsomra）合成中的两种中间体的分析，并通过核磁共振（NMR），密度泛函理论（DFT）和离子迁移谱-质谱（IMS-MS）研究进行了其他分析。 。对于1-取代的1、2、3-三唑，还观察到明显的水/醇损失，但对于异构的2-取代的1、2、3-三唑类似物没有观察到。进行IMS-MS，NMR和DFT研究以表明2-取代的三唑旋转异构体的优选取向远离反应的亲电子中心，而1-取代的三唑的取向紧邻该中心。确定NGP产物的丰

  DOI：

  10.1007/s13361-017-1884-8

文献信息

• Aryl Boronic Esters Are Stable on Silica Gel and Reactive under Suzuki–Miyaura Coupling Conditions
  作者：Naoki Oka、Tsuyoshi Yamada、Hironao Sajiki、Shuji Akai、Takashi Ikawa

  DOI：10.1021/acs.orglett.2c01174

  日期：2022.5.20

  A wide range of aryl boronic 1,1,2,2-tetraethylethylene glycol esters [ArB(Epin)s] were readily synthesized. Purifying aryl boronic esters by conventional silica gel chromatography is generally challenging; however, these introduced derivatives are easily purified on silica gel and isolated in excellent yields. We subjected the purified ArB(Epin) to Suzuki–Miyaura couplings, which provided higher yields

  范围广泛的芳基硼 1,1,2,2-四乙基乙二醇酯 [ArB(Epin)s] 很容易合成。通过常规硅胶色谱法纯化芳基硼酸酯通常具有挑战性。然而，这些引入的衍生物很容易在硅胶上纯化并以优异的收率分离。我们对纯化的 ArB(Epin) 进行 Suzuki-Miyaura 偶联，与使用相应的芳基硼酸或频哪醇酯获得的产物相比，这提供了更高产率的所需联芳基产物。
• Photoinduced Pd-Catalyzed C_sp2–H/C_sp3–H Dehydrocoupling Reaction Employing Polyhaloaromatics as the Dehydrogenating Agent
  作者：Lin Chen、Kai Jiang、Guohui Zeng、Biaolin Yin

  DOI：10.1021/acs.orglett.2c03708

  日期：2022.12.16

  strategy for intermolecular cross-dehydrocoupling of Csp2–H bonds and Csp3–H bonds has been developed with the aid of photoinduced Pd catalysis. Polyhalogenated arenes can be used as the efficient dehydrogenating agent, which enables multifold transfer of carbon radical to avoid the production of stoichiometric or excess wasted arenes. In this strategy, substituted styrenes and N-arylacrylamides with simple

  在光诱导 Pd 催化的帮助下，已经开发了一种用于 C sp2 -H 键和 C sp3 -H 键的分子间交叉脱氢偶联的温和策略。多卤代芳烃可用作有效的脱氢剂，它可以实现碳自由基的多重转移，以避免产生化学计量或过量的废芳烃。在该策略中，取代的苯乙烯和N-芳基丙烯酰胺与简单的醚或酰胺作为偶联伙伴，以中等到良好的产率得到相应的内部烯烃和苯并内酰胺。
• Sodium Chloride Catalyzed Regioselective Trifluoromethylthiolation of Furans
  作者：Frank Glorius、Johannes Ernst、Lena Rakers

  DOI：10.1055/s-0036-1588609

  日期：——

  Here, we report the catalytic trifluoromethylthiolation of furans employing sodium chloride as an inexpensive, abundant and ecologically friendly catalyst. The developed method exhibits perfect regioselectivity and a high functional group tolerance. Furthermore, the robustness of the newly developed method was determined by the additive-based Robustness Screen.
• Copper-catalyzed coupling of polymer bound iodide with organostannanes
  作者：Suk-Ku Kang、Jae-Sun Kim、Seok-Keun Yoon、Kwon-Ho Lim、Seung Soo Yoon

  DOI：10.1016/s0040-4039(98)00446-8

  日期：1998.5

  The copper iodide-catalyzed cross-coupling of polymer bound aryl iodide with organostannanes in N-methyl-2-pyrrolidone (NMP) was accomplished smoothly in the presence of NaCl. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Synthesis and activity of isoleucine sulfonamide derivatives as novel botulinum neurotoxin serotype A light chain inhibitors
  作者：Jordan C. Thompson、Wendy T. Dao、Alex Ku、Sandra L. Rodriguez-Beltran、Martin Amezcua、Alejandra Y. Palomino、Thanh Lien、Nicholas T. Salzameda

  DOI：10.1016/j.bmc.2020.115659

  日期：2020.9

  The botulinum neurotoxin (BoNT) is the most lethal protein known to man causing the deadly disease botulinum. The neurotoxin, composed of a heavy (HC) and light (LC) chain, work in concert to cause muscle paralysis. A therapeutic strategy to treat individuals infected with the neurotoxin is inhibiting the catalytic activity of the BoNT LC. We report the synthesis, inhibition study and computational docking analysis of novel small molecule BoNT/A LC inhibitors. A structure activity relationship study resulted in the discovery of D-isoleucine functionalized with a hydroxamic acid on the C-terminal and a biphenyl with chlorine at C- 2 connected by a sulfonamide linker at the N-terminus. This compound has a measured IC50 of 0.587 mu M for the BoNT/A LC. Computational docking analysis indicates the sulfonamide linker adopts a geometry that is advantageous for binding to the BoNT LC active site. In addition, Arg363 is predicted to be involved in key binding interactions with the scaffold in this study.