6-丙氧基-2-萘甲醛 | 100234-29-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 6-丙氧基-2-萘甲醛
• 英文名称: 6-propoxy-2-naphthaldehyde
• 英文别名: 6-Propoxy-2-naphthaldehyde；6-propoxynaphthalene-2-carbaldehyde
• CAS: 100234-29-5
• 化学式: C₁₄H₁₄O₂
• 分子量: 214.264
• InChiKey: JGZGEAUYRXRJGA-UHFFFAOYSA-N

物化性质

• 熔点：
  188.0-189.1 °C
• 沸点：
  364.3±15.0 °C(Predicted)
• 密度：
  1.114±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-丙氧基-2-萘甲醛 、 N-(3-丁烯-1-基)-4-甲基苯磺酰胺 在 甲基碘化镁 、 NiCl₂BINAP 、 四氯化钛 、 对甲苯磺酸 、 magnesium iodide 作用下， 以 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 192.0h， 生成 4-methyl-N-(2-(trans-2-(6-propoxynaphthalen-2-yl)cyclopropyl)ethyl)benzenesulfonamide
  参考文献：
  名称：

  参与磺酰胺：磺酰胺与烷基氯化物的分子内跨亲电偶联反应。

  摘要：

  由于CN键的固有强度，很少使用胺衍生物作为偶联伴侣。在这里，我们报告了未应变的苄基磺酰胺的第一个交叉亲电子偶联反应。无环和环状苄基磺酰胺与烷基氯化侧基的镍催化的分子内亲电偶联反应生成环丙烷产物。机理实验和DFT计算与通过碘化镁加速苄基磺酰胺的氧化加成反应的反应是一致的。这项工作建立了作为XEC伙伴的中性和非应变胺衍生物，提供了苄基磺酰胺的结构重排，并提供了有关催化剂设计的有价值的信息，以开发新的碳-杂原子键交叉亲电子偶联反应。

  DOI：

  10.1021/acs.joc.9b02603
• 作为产物：
  描述：

  2-溴-6-丙氧基萘 、 N,N-二甲基甲酰胺 在 碘 、 magnesium 、 水 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以25%的产率得到6-丙氧基-2-萘甲醛
  参考文献：
  名称：

  Naphthylisopropylamine and N-benzylamphetamine derivatives as monoamine oxidase inhibitors

  摘要：

  A series of naphthylisopropylamine and N-benzyl-4-methylthioamphetamine derivatives were evaluated as monoamine oxidase inhibitors. Their potencies were compared with those of a series of amphetamine derivatives, to test if the increase of electron richness of the aromatic ring and overall size of the molecule might improve their potency as enzyme inhibitors. Molecular dockings were performed to gain insight regarding the binding mode of these inhibitors and rationalize their different potencies. In the case of naphthylisopropylamine derivatives, the increased electron-donating capacity and size of the aromatic moiety resulting from replacement of the phenyl ring of amphetamine derivatives by a naphthalene system resulted in more potent compounds. In the other case, extension of the arylisopropylamine molecule by N-benzylation of the amino group led to a decrease in potency as monoamine oxidase inhibitors. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.01.074

文献信息

• Unique fluorescent probe for the recognition of late apoptosis via translocation from plasma membrane to nucleus
  作者：Wei Ge、Huina Wang、Xiaofen Wu、Baoli Dong、Qingqing Lu、Minggang Tian

  DOI：10.1016/j.saa.2024.124095

  日期：2024.5

  pathological activities. However, the current fluorescent probes for the detection of late apoptosis were “–” probes, which were facilely interfered by false positive signals caused by inhomogeneous staining and other factors. Herein, a unique fluorescent probe (NPn) discriminating late apoptosis from early apoptosis and heathy status with two different sets of fluorescent signals have been prepared, to overcome

  细胞凋亡是一个重要的生理过程，在关键的生物学和病理活动中发挥着核心作用。但目前检测晚期凋亡的荧光探针均为“-”型探针，容易受到染色不均匀等因素造成的假阳性信号干扰。在此，制备了一种独特的荧光探针（NPn），用两组不同的荧光信号区分晚期凋亡与早期凋亡和健康状态，以克服可能的假阳性信号。 NPn 被设计为对生物膜不可渗透，同时对 DNA/RNA 具有高亲和力，其位于活细胞和早期凋亡细胞的质膜上，而在晚期凋亡细胞中重新定位到细胞核。亲水性胺单元和小离子半径对其膜不渗透性敏感，这通过两个不含胺基的对照分子得到证实。利用该探针，我们成功评估了紫外线照射、鱼藤酮、秋水仙碱和紫杉醇诱导的细胞凋亡，展示了其在生物学研究中的潜在应用。
• Engaging Sulfonamides: Intramolecular Cross-Electrophile Coupling Reaction of Sulfonamides with Alkyl Chlorides
  作者：Erika L. Lucas、Kirsten A. Hewitt、Pan-Pan Chen、Anthony J. Castro、Xin Hong、Elizabeth R. Jarvo

  DOI：10.1021/acs.joc.9b02603

  日期：2020.2.21

  The application of amine derivatives as coupling partners is rare due to the inherent strength of the C-N bond. Herein, we report the first cross-electrophile coupling reaction of unstrained benzylic sulfonamides. Nickel-catalyzed intramolecular cross-electrophile coupling reactions of acyclic and cyclic benzylic sulfonamides with pendant alkyl chlorides generate cyclopropane products. Mechanistic

  由于CN键的固有强度，很少使用胺衍生物作为偶联伴侣。在这里，我们报告了未应变的苄基磺酰胺的第一个交叉亲电子偶联反应。无环和环状苄基磺酰胺与烷基氯化侧基的镍催化的分子内亲电偶联反应生成环丙烷产物。机理实验和DFT计算与通过碘化镁加速苄基磺酰胺的氧化加成反应的反应是一致的。这项工作建立了作为XEC伙伴的中性和非应变胺衍生物，提供了苄基磺酰胺的结构重排，并提供了有关催化剂设计的有价值的信息，以开发新的碳-杂原子键交叉亲电子偶联反应。
• Naphthylisopropylamine and N-benzylamphetamine derivatives as monoamine oxidase inhibitors
  作者：Marcelo Vilches-Herrera、Juan Miranda-Sepúlveda、Marco Rebolledo-Fuentes、Angélica Fierro、Susan Lühr、Patricio Iturriaga-Vasquez、Bruce K. Cassels、Miguel Reyes-Parada

  DOI：10.1016/j.bmc.2009.01.074

  日期：2009.3

  A series of naphthylisopropylamine and N-benzyl-4-methylthioamphetamine derivatives were evaluated as monoamine oxidase inhibitors. Their potencies were compared with those of a series of amphetamine derivatives, to test if the increase of electron richness of the aromatic ring and overall size of the molecule might improve their potency as enzyme inhibitors. Molecular dockings were performed to gain insight regarding the binding mode of these inhibitors and rationalize their different potencies. In the case of naphthylisopropylamine derivatives, the increased electron-donating capacity and size of the aromatic moiety resulting from replacement of the phenyl ring of amphetamine derivatives by a naphthalene system resulted in more potent compounds. In the other case, extension of the arylisopropylamine molecule by N-benzylation of the amino group led to a decrease in potency as monoamine oxidase inhibitors. (C) 2009 Elsevier Ltd. All rights reserved.