12-(Pyridine-3-carbonyloxy)dodecyl pyridine-3-carboxylate | 85018-79-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 12-(Pyridine-3-carbonyloxy)dodecyl pyridine-3-carboxylate
• CAS: 85018-79-7
• 化学式: C₂₄H₃₂N₂O₄
• 分子量: 412.529
• InChiKey: JOYJSWNSSPXGRT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  30
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  78.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  二氯甲烷 、 [Re(CO)₃(phen)Br] 、 12-(Pyridine-3-carbonyloxy)dodecyl pyridine-3-carboxylate 、 silver tetrafluoroborate 以 甲苯 为溶剂， 以26%的产率得到fac,fac-([Re(CO)3(phen)]2(C5H4NCOO(CH2)12OCOC5H4N))(BF4)2*0.75CH2Cl2
  参考文献：
  名称：

  Biologically Compatible, Phosphorescent Dimetallic Rhenium Complexes Linked through Functionalized Alkyl Chains: Syntheses, Spectroscopic Properties, and Applications in Imaging Microscopy

  摘要：

  A range of luminescent, dimetallic complexes based upon the rhenium fac-tricarbonyl diimine core, linked by aliphatic chains of varying lengths and functionality, have been synthesized and their photophysical properties examined. Each complex displays characteristic (MReLdiimineCT)-M-3 emission in aerated acetonitrile solution, with long lifetimes in the range of 129-248 ns and corresponding quantum yields in the range 3.2-8.0%. In aqueous solution, as opposed to acetonitrile, the complexes generally show a small hypsochromic shift in lambda(em) and an extension of the (MLCT)-M-3 lifetime, attributed to a hydrophobically driven association of the alkyl chains with the rhenium-bound diimine units. In live cell imaging experiments using MCF7 cells the complexes all show good uptake by non-energy dependent mechanisms without endosomal entrainment, and with varying propensity to localize in organelles. The degrees of uptake and localization properties are discussed in terms of the length and chemical nature of the linkers, and in terms of the likely interactions between these and the various cellular components encountered.

  DOI：

  10.1021/ic201654d
• 作为产物：
  描述：

  烟酰氯 、 1,12-十二烷二醇 在 三乙胺 作用下， 以 氯仿 为溶剂， 反应 5.0h， 以93%的产率得到12-(Pyridine-3-carbonyloxy)dodecyl pyridine-3-carboxylate
  参考文献：
  名称：

  Biologically Compatible, Phosphorescent Dimetallic Rhenium Complexes Linked through Functionalized Alkyl Chains: Syntheses, Spectroscopic Properties, and Applications in Imaging Microscopy

  摘要：

  A range of luminescent, dimetallic complexes based upon the rhenium fac-tricarbonyl diimine core, linked by aliphatic chains of varying lengths and functionality, have been synthesized and their photophysical properties examined. Each complex displays characteristic (MReLdiimineCT)-M-3 emission in aerated acetonitrile solution, with long lifetimes in the range of 129-248 ns and corresponding quantum yields in the range 3.2-8.0%. In aqueous solution, as opposed to acetonitrile, the complexes generally show a small hypsochromic shift in lambda(em) and an extension of the (MLCT)-M-3 lifetime, attributed to a hydrophobically driven association of the alkyl chains with the rhenium-bound diimine units. In live cell imaging experiments using MCF7 cells the complexes all show good uptake by non-energy dependent mechanisms without endosomal entrainment, and with varying propensity to localize in organelles. The degrees of uptake and localization properties are discussed in terms of the length and chemical nature of the linkers, and in terms of the likely interactions between these and the various cellular components encountered.

  DOI：

  10.1021/ic201654d

文献信息

• Biologically Compatible, Phosphorescent Dimetallic Rhenium Complexes Linked through Functionalized Alkyl Chains: Syntheses, Spectroscopic Properties, and Applications in Imaging Microscopy
  作者：Rebeca G. Balasingham、Flora L. Thorp-Greenwood、Catrin F. Williams、Michael P. Coogan、Simon J. A. Pope

  DOI：10.1021/ic201654d

  日期：2012.2.6

  A range of luminescent, dimetallic complexes based upon the rhenium fac-tricarbonyl diimine core, linked by aliphatic chains of varying lengths and functionality, have been synthesized and their photophysical properties examined. Each complex displays characteristic (MReLdiimineCT)-M-3 emission in aerated acetonitrile solution, with long lifetimes in the range of 129-248 ns and corresponding quantum yields in the range 3.2-8.0%. In aqueous solution, as opposed to acetonitrile, the complexes generally show a small hypsochromic shift in lambda(em) and an extension of the (MLCT)-M-3 lifetime, attributed to a hydrophobically driven association of the alkyl chains with the rhenium-bound diimine units. In live cell imaging experiments using MCF7 cells the complexes all show good uptake by non-energy dependent mechanisms without endosomal entrainment, and with varying propensity to localize in organelles. The degrees of uptake and localization properties are discussed in terms of the length and chemical nature of the linkers, and in terms of the likely interactions between these and the various cellular components encountered.