1-phenyl-5-(4-N,N-dimethylaminophenyl)-1,4-pentadiyn-3-one | 242487-93-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-phenyl-5-(4-N,N-dimethylaminophenyl)-1,4-pentadiyn-3-one
• 英文别名: 1-[4-(dimethylamino)phenyl]-5-phenyl-1,4-pentadiyn-3-one；1-[4-(Dimethylamino)phenyl]-5-phenylpenta-1,4-diyn-3-one
• CAS: 242487-93-0
• 化学式: C₁₉H₁₅NO
• 分子量: 273.334
• InChiKey: QTNVBYHWICBLIB-UHFFFAOYSA-N

物化性质

• 沸点：
  432.8±47.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-phenyl-5-(4-N,N-dimethylaminophenyl)-1,4-pentadiyn-3-one 在 乙醇 、 sodium ethanolate 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 3.0h， 生成 2-(4-Dimethylamino-phenyl)-4,6-diphenyl-4H-selenopyran-4-ol
  参考文献：
  名称：

  Synthesis and Evaluation of Chalcogenopyrylium Dyes as Potential Sensitizers for the Photodynamic Therapy of Cancer

  摘要：

  A series of thiopyrylium (2), selenopyrylium (3), and telluropyrylium dyes (4) was prepared via the addition of Grignard reagents to either 2,6-di(4-dimethylamino)phenylchalcogenopyran-4-ones (5a) or 2-[4-(dimethylamino)phenyl] -6-phenylchalcogenopyran-4-ones (5b) followed by elimination and ion exchange to give the chloride salts. The absorption spectra and quantum yields for singlet oxygen generation of these dyes suggested that the dyes would have utility as sensitizers for PDT. Selenopyrylium dyes 3a and 3d with quantum yields for singlet oxygen generation of 0.040 and 0.045, respectively, were phototoxic to Colo-26 cells in culture. The toxicity of the dyes 2-4 was evaluated in clonogenic assays of human carcinoma cell lines. Importantly, the presence of a sulfur, selenium, or tellurium heteroatom in the molecules had no predictable impact on the toxicity of any particular dye set. Substituents at the 2-, 4-, and 6-positions of the dye had a much greater impact on cytotoxicity. The IC50 values determined in the clonogenic assays did not correlate with chemical properties in the dye molecules such as reduction potential or lipophilicity. Initial in vivo toxicity studies showed no toxicity for these dyes at dosages between 7.2 and 38 mu mol/kg in BALB/c mice.

  DOI：

  10.1021/jm990245q
• 作为产物：
  描述：

  4-二甲基氨基苯乙炔 在 manganese(IV) oxide 、 正丁基锂 作用下， 以 二氯甲烷 为溶剂， 反应 74.67h， 生成 1-phenyl-5-(4-N,N-dimethylaminophenyl)-1,4-pentadiyn-3-one
  参考文献：
  名称：

  硫属元素吡喃二酮由硫属元素二钠加成到1,4-戊二炔-3-酮中。烯醇醚作为中间体的作用

  摘要：

  通过在乙醇钠/乙醇中将乙醇加成到1，4-戊二炔-3-酮2中，形成E-和Z-异构体的混合物的烯醇醚9。烯醇醚与硫属元素化物二钠反应，以高收率得到相应的带有烷基，芳基或杂芳基取代基的2，6-二取代硫属元素吡喃酮类化合物1，这是反应的唯一杂环产物。二炔酮2与硫属元素化物二钠反应，得到产物混合物，其中硫属元素合吡喃酮类1是次要成分，而二氢硫属元素芴3是主要产物。向二酮2b中添加硫化氢乙醇中的产物混合物与乙醇中乙醇钠中的硫化钠硫化钠加至2b中观察到的几乎相同。描述了用于向2和9二者中添加硫属元素氢和硫属元素二钠的中间体，其导致杂环产物。

  DOI：

  10.1002/jhet.5570360322

文献信息

• Chalcogenopyranones from disodium chalcogenide additions to 1,4-pentadiyn-3-ones. The role of enol ethers as intermediates
  作者：Kristi Leonard、Marina Nelen、Madhavi Raghu、Michael R. Detty

  DOI：10.1002/jhet.5570360322

  日期：1999.5

  chalcogenides to give mixtures of products in which the chalcogenopyranones 1 are minor components and the dihydrochalcogenophenes 3 are the major products. The addition of hydrogen sulfide to diynone 2b in ethanol gives a product mixture nearly identical to that observed for the addition of disodium sulfide in sodium ethoxide in ethanol to 2b. Intermediates for the addition of hydrogen chalcogenides and

  通过在乙醇钠/乙醇中将乙醇加成到1，4-戊二炔-3-酮2中，形成E-和Z-异构体的混合物的烯醇醚9。烯醇醚与硫属元素化物二钠反应，以高收率得到相应的带有烷基，芳基或杂芳基取代基的2，6-二取代硫属元素吡喃酮类化合物1，这是反应的唯一杂环产物。二炔酮2与硫属元素化物二钠反应，得到产物混合物，其中硫属元素合吡喃酮类1是次要成分，而二氢硫属元素芴3是主要产物。向二酮2b中添加硫化氢乙醇中的产物混合物与乙醇中乙醇钠中的硫化钠硫化钠加至2b中观察到的几乎相同。描述了用于向2和9二者中添加硫属元素氢和硫属元素二钠的中间体，其导致杂环产物。
• Synthesis and Evaluation of Chalcogenopyrylium Dyes as Potential Sensitizers for the Photodynamic Therapy of Cancer
  作者：Kristi A. Leonard、Marina I. Nelen、Todd P. Simard、Sherry R. Davies、Sandra O. Gollnick、Allan R. Oseroff、Scott L. Gibson、Russell Hilf、Lan Bo Chen、Michael R. Detty

  DOI：10.1021/jm990245q

  日期：1999.9.1

  A series of thiopyrylium (2), selenopyrylium (3), and telluropyrylium dyes (4) was prepared via the addition of Grignard reagents to either 2,6-di(4-dimethylamino)phenylchalcogenopyran-4-ones (5a) or 2-[4-(dimethylamino)phenyl] -6-phenylchalcogenopyran-4-ones (5b) followed by elimination and ion exchange to give the chloride salts. The absorption spectra and quantum yields for singlet oxygen generation of these dyes suggested that the dyes would have utility as sensitizers for PDT. Selenopyrylium dyes 3a and 3d with quantum yields for singlet oxygen generation of 0.040 and 0.045, respectively, were phototoxic to Colo-26 cells in culture. The toxicity of the dyes 2-4 was evaluated in clonogenic assays of human carcinoma cell lines. Importantly, the presence of a sulfur, selenium, or tellurium heteroatom in the molecules had no predictable impact on the toxicity of any particular dye set. Substituents at the 2-, 4-, and 6-positions of the dye had a much greater impact on cytotoxicity. The IC50 values determined in the clonogenic assays did not correlate with chemical properties in the dye molecules such as reduction potential or lipophilicity. Initial in vivo toxicity studies showed no toxicity for these dyes at dosages between 7.2 and 38 mu mol/kg in BALB/c mice.