1,2-bis((2-methoxyphenyl)ethynyl)benzene | 823226-90-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,2-bis((2-methoxyphenyl)ethynyl)benzene
• 英文别名: 1,2-bis(2-anisolyl)ethynylbenzene；Benzene, 1,2-bis[(2-methoxyphenyl)ethynyl]-；1,2-bis[2-(2-methoxyphenyl)ethynyl]benzene
• CAS: 823226-90-0
• 化学式: C₂₄H₁₈O₂
• 分子量: 338.406
• InChiKey: UPKOWKBDKQMHBY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,2-bis((2-methoxyphenyl)ethynyl)benzene 在 copper(ll) bromide 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以91%的产率得到11-bromo-6-(2-methoxyphenyl)indeno[1,2-c]chromene
  参考文献：
  名称：

  芳基二炔与茚并[1,2- c ]亚甲基衍生物的卤素介导级联环化反应

  摘要：

  描述了芳基二炔的卤素介导的环化反应以产生卤化的茚并[1,2- c ]亚甲基衍生物。用一当量的碘处理芳基二炔1可以得到良好的化学收率的碘化茚并[1,2- c ]苯二酮3。当将两当量的碘用于反应混合物中时，获得二聚体9作为主要产物。在另一方面，溴化亚铜的两个当量的反应2用化合物1，得到溴化茚并[1,2- c ^ ]苯并吡喃4。为了了解取代基如何影响环化途径，对含甲氧基，羧基，氨基和硫化物取代基的分子进行了碘介导的环化反应的DFT计算。

  DOI：

  10.1021/acs.joc.7b00538
• 作为产物：
  描述：

  1,2-二碘苯 在 四(三苯基膦)钯 copper(l) iodide 、 potassium carbonate 、 正丁胺 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 6.0h， 生成 1,2-bis((2-methoxyphenyl)ethynyl)benzene
  参考文献：
  名称：

  Cytotoxicities, cell cycle and caspase evaluations of 1,6-diaryl-3(Z)-hexen-1,5-diynes, 2-(6-aryl-3(Z)-hexen-1,5-diynyl)anilines and their derivatives

  摘要：

  Compounds 3, 6-7, 9-10, 15-17, and 20-21 showed growth inhibition effects on a full panel of 60 human cancer cell lines, and most of the average IC50 values of the indicated analogues were from < 0.01 to 96.6 mu M, in which analogues 16 and 17 revealed the highest cytotoxic activity with the cancer cell lines at 10(-7) M concentration range. During the cell cycle analysis, a moderate to high apoptotic progress induction was shown by 3, 9, 16-17, and 20 compared with the control, which 2-(6-(2-thienyl)-3(Z)-hexen-1,5-diynyl)aniline 16 showed the highest apoptotic effect. Structures 16-17 displayed a significant G2/M phase arrest in the cell growth cycle compared with other derivatives, which the proportions of the G2/M phase cells were accumulated to 71.5% and 82.6%, respectively. Moreover, the colorimetric assay of 16-17 also provided advanced evidence to the relationship between the compounds and the caspase-3 enzyme, which was one of the major promoters of apoptotic effect. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.02.062

文献信息

• Triflic Acid Mediated Cascade Cyclization of Aryldiynes for the Synthesis of Indeno[1,2-<i>c</i>]chromenes: Application to Dye-Sensitized Solar Cells
  作者：Hua Jiang、Giovanni Ferrara、Xuan Zhang、Kazuaki Oniwa、Ashraful Islam、Liyuan Han、Ying-Ji Sun、Ming Bao、Naoki Asao、Yoshinori Yamamoto、Tienan Jin

  DOI：10.1002/chem.201405860

  日期：2015.3.2

  A new triflic acid (TfOH)‐mediated cascade cyclization of ortho‐anisole‐substituted aryldiynes is described for the construction of indeno[1,2‐c]chromenes. The cascade cyclization proceeds through an unusual TfOH‐induced alkyne‐alkyne cyclization followed by nucleophilic attack of the methoxy group on the benzylidene cation, which is completely different to the cyclization of ortho‐aniline‐ or ort

  描述了一种新的由三氟甲磺酸（TfOH）介导的邻苯甲醚取代的芳基二炔的级联环化反应，用于构建茚并[1,2- c ]苯二酮。级联环化是通过不寻常的TfOH诱导的炔烃-炔烃环化进行的，随后甲氧基对苄叉基阳离子的亲核攻击，这与邻苯胺或邻苯硫基苯甲醚取代的芳基二炔的环化完全不同。合成了以茚并[1,2- c ]亚甲基骨架为供体和π-连接基的一类新型有机染料。这些化合物在染料敏化太阳能电池（DSC）中表现出很高的光伏性能。
• Halogen-Mediated Cascade Cyclization Reaction of Aryldiynes to Indeno[1,2-<i>c</i>]chromene Derivatives
  作者：Chin-Chau Chen、Man-Yun Wu、Hsing-Yin Chen、Ming-Jung Wu

  DOI：10.1021/acs.joc.7b00538

  日期：2017.6.16

  halogenated indeno[1,2-c]chromene derivatives is described. Treatment of aryldiynes 1 with one equivalent of iodine gave iodinated indeno[1,2-c]chromenes 3 in good chemical yields. When two equivalents of iodine were employed into the reaction mixture, dimer 9 was obtained as the major products. On the other hand, reaction of two equivalents of CuBr2 with compounds 1 gave the brominated indeno[1,2-c]chromenes

  描述了芳基二炔的卤素介导的环化反应以产生卤化的茚并[1,2- c ]亚甲基衍生物。用一当量的碘处理芳基二炔1可以得到良好的化学收率的碘化茚并[1,2- c ]苯二酮3。当将两当量的碘用于反应混合物中时，获得二聚体9作为主要产物。在另一方面，溴化亚铜的两个当量的反应2用化合物1，得到溴化茚并[1,2- c ^ ]苯并吡喃4。为了了解取代基如何影响环化途径，对含甲氧基，羧基，氨基和硫化物取代基的分子进行了碘介导的环化反应的DFT计算。
• Cytotoxicities, cell cycle and caspase evaluations of 1,6-diaryl-3(Z)-hexen-1,5-diynes, 2-(6-aryl-3(Z)-hexen-1,5-diynyl)anilines and their derivatives
  作者：Chi-Fong Lin、Yu-Hsiang Lo、Ming-Chu Hsieh、Yi-Hua Chen、Jeh-Jeng Wang、Ming-Jung Wu

  DOI：10.1016/j.bmc.2005.02.062

  日期：2005.5

  Compounds 3, 6-7, 9-10, 15-17, and 20-21 showed growth inhibition effects on a full panel of 60 human cancer cell lines, and most of the average IC50 values of the indicated analogues were from < 0.01 to 96.6 mu M, in which analogues 16 and 17 revealed the highest cytotoxic activity with the cancer cell lines at 10(-7) M concentration range. During the cell cycle analysis, a moderate to high apoptotic progress induction was shown by 3, 9, 16-17, and 20 compared with the control, which 2-(6-(2-thienyl)-3(Z)-hexen-1,5-diynyl)aniline 16 showed the highest apoptotic effect. Structures 16-17 displayed a significant G2/M phase arrest in the cell growth cycle compared with other derivatives, which the proportions of the G2/M phase cells were accumulated to 71.5% and 82.6%, respectively. Moreover, the colorimetric assay of 16-17 also provided advanced evidence to the relationship between the compounds and the caspase-3 enzyme, which was one of the major promoters of apoptotic effect. (c) 2005 Elsevier Ltd. All rights reserved.