4-hydroxyethoxy-2-methoxybenzaldehyde | 1220703-12-7

• 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-hydroxyethoxy-2-methoxybenzaldehyde
• 英文别名: 4-(2-hydroxyethoxy)-2-methoxybenzaldehyde；4-(2-Hydroxyethoxy)-2-methoxybenzaldehyde
• CAS: 1220703-12-7
• 化学式: C₁₀H₁₂O₄
• mdl: MFCD24390864
• 分子量: 196.203
• InChiKey: GDFVEFFCUROETD-UHFFFAOYSA-N

物化性质

• 沸点：
  380.6±27.0 °C(Predicted)
• 密度：
  1.202±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-hydroxyethoxy-2-methoxybenzaldehyde 在 哌啶 、 盐酸 、 potassium carbonate 、 对甲苯磺酸 、 barium(II) hydroxide 作用下， 以 水 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  基于 BODIPY 的高选择性、红色发射荧光指示剂，用于细胞内 Mg2+ 成像†

  摘要：

  大多数 Mg 2+荧光指示剂对其他二价阳离子（尤其是 Ca 2+ ）的选择性较差，因此不能提供涉及此类金属的过程中细胞 Mg 2+浓度的可靠信息。我们报告了一套新的高选择性荧光指示剂，其基于烷氧基苯乙烯基功能化的 BODIPY 荧光团，并装饰有 4-oxo-4 H -quinolizine-3-carbic Acid 金属结合部分。新型传感器MagQ1和MagQ2在 600 nm 以上显示吸收和发射最大值，在水性缓冲液中配位 Mg 2+后，荧光增强了 29 倍，并具有良好的量子产率 ( Φ > 0.3)。对 Mg 2+的荧光响应不受细胞环境中通常存在的竞争性二价阳离子的影响，并且在生理相关范围内表现出最小的 pH 依赖性。装饰苯乙烯基BODIPY核心的烷氧基的选择不会影响化合物的基本光物理和金属结合特性，但对其细胞内保留具有显着影响，因此对其通过荧光成像检测细胞Mg 2+的适用性具有显着影

  DOI：

  10.1039/c8tb01599f
• 作为产物：
  描述：

  4-羟基-2-甲氧基苯甲醛 、 2-溴乙醇 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以72%的产率得到4-hydroxyethoxy-2-methoxybenzaldehyde
  参考文献：
  名称：

  基于 BODIPY 的高选择性、红色发射荧光指示剂，用于细胞内 Mg2+ 成像†

  摘要：

  大多数 Mg 2+荧光指示剂对其他二价阳离子（尤其是 Ca 2+ ）的选择性较差，因此不能提供涉及此类金属的过程中细胞 Mg 2+浓度的可靠信息。我们报告了一套新的高选择性荧光指示剂，其基于烷氧基苯乙烯基功能化的 BODIPY 荧光团，并装饰有 4-oxo-4 H -quinolizine-3-carbic Acid 金属结合部分。新型传感器MagQ1和MagQ2在 600 nm 以上显示吸收和发射最大值，在水性缓冲液中配位 Mg 2+后，荧光增强了 29 倍，并具有良好的量子产率 ( Φ > 0.3)。对 Mg 2+的荧光响应不受细胞环境中通常存在的竞争性二价阳离子的影响，并且在生理相关范围内表现出最小的 pH 依赖性。装饰苯乙烯基BODIPY核心的烷氧基的选择不会影响化合物的基本光物理和金属结合特性，但对其细胞内保留具有显着影响，因此对其通过荧光成像检测细胞Mg 2+的适用性具有显着影

  DOI：

  10.1039/c8tb01599f

文献信息

• [EN] PRODRUGS OF OXAZOLIDINONE CETP INHIBITORS<br/>[FR] PROMÉDICAMENTS D'INHIBITEURS DE CETP À BASE D'OXAZOLIDINONE
  申请人：MERCK SHARP & DOHME

  公开号：WO2010039474A1

  公开（公告）日：2010-04-08

  The compounds of Formula I are prodrugs of CETP inhibitors having a central oxazolidinone ring. The compounds cyclize by the elimination of HX to form an oxazolidinone ring after administration to a patient.

  公式I的化合物是CETP抑制剂的前药，具有中心噁唑烷酮环。这些化合物在给药后通过消除HX而环化，形成噁唑烷酮环。
• Method for synthesis of 4-OH substituted anabaseine derivative
  申请人：INSTITUTE OF NUCLEAR ENERGY RESEARCH, ATOMIC ENERGY COUNCIL, EXECUTIVE YUAN, R.O.C.

  公开号：US09567315B1

  公开（公告）日：2017-02-14

  A method for synthesis of 4-OH substituted anabaseine derivative which is used as an α7 receptor agonist is revealed. A nucleophilic substitution reaction of δ-valerolactam with ethyl nicotinate is carried out to get an intermediate product. Then heat the intermediate product under reflux with concentrated hydrochloric acid to get a cyclized product-anabaseine. Next anabaseine and 4-hydroxyethoxy-2-methoxybenzaldehyde are reacted under concentrated hydrochloric acid catalysis to get a 4-OH anabaseine derivative 3-[(4-Hydroxyethoxy-2-methoxy)-benzylidene]anabaseine. The 4-OH anabaseine derivative is synthesized and prepared easily by the present invention. Not only the steps for synthesis are simplified, the yield is as high as 60%. The product can be mass-produced.

  揭示了一种合成4-OH取代的阿巴西尼衍生物的方法，该衍生物被用作α7受体激动剂。将δ-戊内酯与乙基烟酸酯进行亲核取代反应，得到中间产物。然后将中间产物在浓盐酸回流条件下加热，得到环化产物-阿巴西尼。接下来，在浓盐酸催化下，阿巴西尼与4-羟基乙氧基-2-甲氧基苯甲醛反应，得到4-OH阿巴西尼衍生物3-[(4-羟基乙氧基-2-甲氧基)-苯甲亚甲基]阿巴西尼。本发明通过简化合成步骤，以高达60%的产率轻松合成和制备4-OH阿巴西尼衍生物。该产品可大规模生产。
• PRODRUGS OF OXAZOLIDINONE CETP INHIBITORS
  申请人：Mills Sander G.

  公开号：US20110218177A1

  公开（公告）日：2011-09-08

  The compounds of Formula I are pro-drugs of CETP inhibitors having a central oxazolidinone ring. The compounds cyclize by the elimination of HX to form an oxazolidinone ring after administration to a patient.

  公式I的化合物是具有中心噁唑烷环的CETP抑制剂前药。这些化合物在给患者使用后通过HX的消除环化形成噁唑烷环。
• Prodrugs of oxazolidinone CETP inhibitors
  申请人：Mills Sander G.

  公开号：US08354454B2

  公开（公告）日：2013-01-15

  The compounds of Formula I are pro-drugs of CETP inhibitors having a central oxazolidinone ring. The compounds cyclize by the elimination of HX to form an oxazolidinone ring after administration to a patient.

  式I的化合物是具有中央噁唑烷环的CETP抑制剂的前药。这些化合物在给患者使用后通过消除HX环化形成噁唑烷环。
• Reactive Fluorescence Turn-On Probes for Fluoride Ions in Purely Aqueous Media Fabricated from Functionalized Responsive Block Copolymers
  作者：Yanyan Jiang、Xianglong Hu、Jinming Hu、Hao Liu、Hui Zhong、Shiyong Liu

  DOI：10.1021/ma2018588

  日期：2011.11.22

  We report on the fabrication of a novel type of responsive double double hydrophilic block copolymer (DHBC)-based highly selective and sensitive fluorescence "turn on" reactive probes for fluoride ions (F-) working in purely aqueous media by exploiting F--induced cyclization reaction of nonfluorescent moieties to induce the formation of fluorescent coumarin moieties, as inspired by the previous; work of the Swager research group (Angew. Chem. Int. Ed. 2003, 42, 4803). Diblock copolymers bearing F--reactive moieties (SiCouMA) in the thermoresponsive block, PEO-b-P(MEO(2)MA-co-OEGMA-co-SiCouMA), were synthesized at first via reversible addition-fragmentation chain transfer (RAFT) technique followed by postmodification, where PEO, MEO(2)MA, and OEGMA are poly(ethylene glycol), di(ethylene glycol) monomethyl ether methacrylate, and oligo(ethylene glycol) monomethyl ether methacrylate, respectively. As-synthesized diblock copolymers molecularly dissolve in water at room temperature and self-assemble into micellar nanoparticles above the critical micellization temperature (33 degrees C). In the presence of F- ions, deprotection of nonfluorescent SiCouMA moieties followed by spontaneous cyclization reaction. leads to the formation of highly fluorescent coumarin residues (CouMA). Thus, PEO-b-P(MEO(2)MA-co-OEGMA-co-SiCouMA) diblock copolymers can serve as highly efficient and selective fluorescence "turn-on" reaction probes for F ions in aqueous media. In the range of 0-1600 equiv of F- ions, diblock unimers and micellar solutions at 20 and 40 degrees C exhibit similar to 88-fold and similar to 30-fold increase in fluorescence emission intensity (20 mm incubation time), respectively. The detection limits were determined to be 0.065 and 0.05 ppm for diblock unimers and micelles, respectively. Most importantly, in the low F- concentration range, excellent linear correlation between F- concentration and emission intensity was observed (0-15 ppm for unimers at 20 degrees C and 0-8 ppm for micelles at 40 degrees C). Interestingly, upon complete transformation of nonfluorescent SiCouMA moieties into fluorescent CouMA, the emission intensity of diblock copolymer solution decreases linearly with temperatures in the range of 20-60 degrees C, suggesting its further application as fluorometric temperature sensors. To the best of our knowledge, this work represents the first example of F--reactive polymeric probes working in purely aqueous media, which are capable of highly sensitive and selective fluorescent F- sensing in the form of both unimers and micellar nanoparticles.