1-(4-ethynylphenyl)naphthalene | 1578111-06-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(4-ethynylphenyl)naphthalene
• 英文别名: 1-Naphtylphenylacetylene
• CAS: 1578111-06-4
• 化学式: C₁₈H₁₂
• 分子量: 228.293
• InChiKey: PTUDLJIJHVXVKQ-UHFFFAOYSA-N

物化性质

• 沸点：
  362.8±21.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-(4-ethynylphenyl)naphthalene 在 palladium diacetate 、 一氯化碘 、 三(2,6-二甲氧基苯基)磷 、 三苯基膦 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 5.16h， 生成 4-methyl-6-(4-(naphthalen-1-yl)phenyl)-2H-pyran-2-one
  参考文献：
  名称：

  Discovery of a novel series of N -hydroxypyridone derivatives protecting astrocytes against hydrogen peroxide-induced toxicity via improved mitochondrial functionality

  摘要：

  Astrocytes play a key role in brain homeostasis, protecting neurons against neurotoxic stimuli such as oxidative stress. Therefore, the neuroprotective therapeutics that enhance astrocytic functionality has been regarded as a promising strategy to reduce brain damage. We previously reported that ciclopirox, a well-known antifungal N-hydroxypyridone compound, protects astrocytes from oxidative stress by enhancing mitochondrial function. Using the N-hydroxypyridone scaffold, we have synthesized a series of cytoprotective derivatives. Mitochondrial activity assay showed that N-hydroxypyridone derivatives with biphenyl group have comparable to better protective effects than ciclopirox in astrocytes exposed to H2O2. N-hydroxypyridone derivatives, especially 11g, inhibited membrane-induced deterioration of mitochondrial membrane potential and oxygen consumption rate, and significantly improved cell viability of astrocytes. The results indicate that the N-hydroxypyridone motif can provide a novel cytoprotective scaffold for astrocytes via enhancing mitochondrial functionality. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.12.052
• 作为产物：
  描述：

  (4-溴苯基乙炔基)三甲基硅烷 在 bis-triphenylphosphine-palladium(II) chloride 、 sodium carbonate 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 水 为溶剂， 反应 3.0h， 生成 1-(4-ethynylphenyl)naphthalene
  参考文献：
  名称：

  Discovery of a novel series of N -hydroxypyridone derivatives protecting astrocytes against hydrogen peroxide-induced toxicity via improved mitochondrial functionality

  摘要：

  Astrocytes play a key role in brain homeostasis, protecting neurons against neurotoxic stimuli such as oxidative stress. Therefore, the neuroprotective therapeutics that enhance astrocytic functionality has been regarded as a promising strategy to reduce brain damage. We previously reported that ciclopirox, a well-known antifungal N-hydroxypyridone compound, protects astrocytes from oxidative stress by enhancing mitochondrial function. Using the N-hydroxypyridone scaffold, we have synthesized a series of cytoprotective derivatives. Mitochondrial activity assay showed that N-hydroxypyridone derivatives with biphenyl group have comparable to better protective effects than ciclopirox in astrocytes exposed to H2O2. N-hydroxypyridone derivatives, especially 11g, inhibited membrane-induced deterioration of mitochondrial membrane potential and oxygen consumption rate, and significantly improved cell viability of astrocytes. The results indicate that the N-hydroxypyridone motif can provide a novel cytoprotective scaffold for astrocytes via enhancing mitochondrial functionality. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.12.052

文献信息

• PHENANTHRENE DERIVATIVE, AND MATERIAL FOR ORGANIC EL ELEMENT
  申请人：Kawamura Masahiro

  公开号：US20100331585A1

  公开（公告）日：2010-12-30

  A phenanthrene derivative is represented by a formula (1) below. In the formula (1), Ar 1 and Ar 2 each represent an aromatic hydrocarbon ring group having 6 to 18 carbon atoms for forming the ring. The aromatic hydrocarbon ring group contains none of anthracene skeleton, pyrene skeleton, aceanthrylene skeleton and naphthacene skeleton. R 1 represents a substituent, the number of which may be 0, 1 or more. R 1 may be bonded in any position of the phenanthrene skeleton. n and m each represent an integer of 1 to 3. k represents an integer of 0 to 8.

  一个菲的衍生物由下面的公式（1）表示。在公式（1）中，Ar1和Ar2分别代表含有6到18个碳原子形成环的芳香烃环基团。芳香烃环基团不包含蒽骨架、芘骨架、乙酰芘骨架和萘骨架。R1代表一个取代基，其数量可以是0、1或更多。R1可以连接在菲的骨架的任何位置。n和m分别代表1到3的整数。k代表0到8的整数。
• [4 + 2] Annulation of Donor–Acceptor Cyclopropanes with Acetylenes Using 1,2-Zwitterionic Reactivity
  作者：Roman A. Novikov、Anna V. Tarasova、Dmitry A. Denisov、Denis D. Borisov、Victor A. Korolev、Vladimir P. Timofeev、Yury V. Tomilov

  DOI：10.1021/acs.joc.7b00209

  日期：2017.3.3

  of donor–acceptor cyclopropanes with acetylenes under the effect of anhydrous GaCl3 using 1,2-zwitterion reactivity was elaborated. The reaction opens access to substituted dihydronaphthalenes, naphthalenes, and other fused carbocycles. The direction of the reaction can be efficiently controlled by temperature.

  拟订了一种新方法，用于在无水GaCl 3的作用下使用1,2-两性离子反应性将供体-受体环丙烷与乙炔环化[4 + 2] 。该反应打开了进入取代的二氢萘，萘和其他稠合碳环的通道。反应的方向可以通过温度有效地控制。
• Cu-catalyzed coupling-cyclization in PEG 400 under ultrasound: a highly selective and greener approach towards isocoumarins
  作者：R. Gangadhara Chary、G. Rajeshwar Reddy、Y. S. S. Ganesh、K. Vara Prasad、S. K. Phani Chandra、Soumita Mukherjee、Manojit Pal

  DOI：10.1039/c3ra40969d

  日期：——

  The combination of CuI–K2CO3-PEG 400 facilitated the coupling-cyclization of o-iodobenzoic acid with terminal alkynes under ultrasound, affording a greener and practical approach towards 3-substituted isocoumarins with remarkable regioselectivity. This inexpensive and Pd and ligand free methodology gave rise to various isocoumarins of potential pharmacological interest.

  CuI–K2CO3-PEG 400 的组合在超声波作用下促进了邻碘苯甲酸与末端炔烃的偶联-环化反应，提供了一种更绿色且实用的方法来合成具有显著区域选择性的3-取代异香豆素。这种廉价且不使用钯和配体的方法学产生了多种具有潜在药理学兴趣的异香豆素。
• Discovery of a novel series of N -hydroxypyridone derivatives protecting astrocytes against hydrogen peroxide-induced toxicity via improved mitochondrial functionality
  作者：Sarbjit Singh、Ja-Il Goo、Hyojin Noh、Sung Jae Lee、Myoung Woo Kim、Hyejun Park、Hitesh B. Jalani、Kyeong Lee、Chunsook Kim、Won-Ki Kim、Chung Ju、Yongseok Choi

  DOI：10.1016/j.bmc.2016.12.052

  日期：2017.2

  Astrocytes play a key role in brain homeostasis, protecting neurons against neurotoxic stimuli such as oxidative stress. Therefore, the neuroprotective therapeutics that enhance astrocytic functionality has been regarded as a promising strategy to reduce brain damage. We previously reported that ciclopirox, a well-known antifungal N-hydroxypyridone compound, protects astrocytes from oxidative stress by enhancing mitochondrial function. Using the N-hydroxypyridone scaffold, we have synthesized a series of cytoprotective derivatives. Mitochondrial activity assay showed that N-hydroxypyridone derivatives with biphenyl group have comparable to better protective effects than ciclopirox in astrocytes exposed to H2O2. N-hydroxypyridone derivatives, especially 11g, inhibited membrane-induced deterioration of mitochondrial membrane potential and oxygen consumption rate, and significantly improved cell viability of astrocytes. The results indicate that the N-hydroxypyridone motif can provide a novel cytoprotective scaffold for astrocytes via enhancing mitochondrial functionality. (C) 2017 Elsevier Ltd. All rights reserved.