2,5-(N,N,N',N'-tetramethyldiamino)benzaldehyde | 591249-83-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,5-(N,N,N',N'-tetramethyldiamino)benzaldehyde
• 英文别名: 2,5-(N,N,N',N'-tetramethylamino)benzaldehyde；5-methoxy-2-dimethylaminobenzaldehyde；2,5-Bis(dimethylamino)benzaldehyde
• CAS: 591249-83-1
• 化学式: C₁₁H₁₆N₂O
• 分子量: 192.261
• InChiKey: LRVCSYNKZAJQSF-UHFFFAOYSA-N

物化性质

• 沸点：
  334.7±27.0 °C(Predicted)
• 密度：
  1.085±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,5-(N,N,N',N'-tetramethyldiamino)benzaldehyde 在 palladium on activated charcoal 氢气 、 sodium 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、500.0 kPa 条件下， 反应 10.0h， 生成 ethyl 3-[2,5-(N,N,N',N'-tetramethylamino)phenyl]propionate
  参考文献：
  名称：

  Synthesis of Aryl-Substituted 1,3-Butadiones

  摘要：

  The synthesis of several electron donor substituted 1-aryl-1,3-butadiones and their use as ligands in the formation of scandium(III) complexes is reported.

  DOI：

  10.1081/scc-120016361
• 作为产物：
  描述：

  N,N,N',N'-四甲基对苯二胺 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 8.0h， 生成 2,5-(N,N,N',N'-tetramethyldiamino)benzaldehyde
  参考文献：
  名称：

  Charge transfer in covalently-linked porphyrin-donor complexes from picosecond transient absorption spectroscopy

  摘要：

  Octaalkyl free base porphyrins have been synthesized with covalently attached electron donors at a single meso position. Singlet-state lifetimes were determined from fluorescence quenching in three solvents and were found to be less-than-or-equal-to 1.5 ps for the N,N,N,N'-tetramethyl-1,4-phenylenediamine (TMPD) appended complex, 1.3 ns for the phenyl-TMPD-appended complex, and greater-than-or-equal-to 5 ns for the phertyl-appended, N,N-dimethylaniline (DMA) appended, and DMA-TMPD-appended porphyrin complexes in o-difluorobenzene. Single photon counting measurements and fluorescence quantum yield quenching studies of the phenyl-appended control and phenyl-TMPD charge-transfer complex gave 14 +/- 3 and 2 +/- 0.3 ns excited-state lifetimes, respectively. Fluorescence quantum yields of the TMPD and phenyl-TMPD porphyrins were higher in solvents with lower dielectric constants. Picosecond absorption spectroscopy was performed on molecules exhibiting fluorescence quenching to characterize the charge-transfer state and to determine the recombination kinetics. Conclusive evidence of charge transfer was obtained by observing the donor cation absorption at 606 nm for the TMPD and phenyl-TMPD porphyrins. Picosecond absorption changes in the 380-500-nm region are complete within 50 ps for the TMPD-appended free base porphyrin and 11.5 ns for the phenyl-TMPD-appended free base porphyrin. First-order kinetic analysis indicates that the charge recombination rates are 26 +/- 3 ps and 3.5 +/- 0.4 ns for the TMPD-appended and phenyl-TMPD-appended complexes, respectively. These data yield beta = 0.8-1.1 angstrom-1 for the exponent in the distance dependence of the electron-transfer rate, exp{-beta(r-r0)}. Inasmuch as similar beta values have been determined for electron transfer through saturated bonds, it can be concluded that the pi system of the meso substituents is ineffective in mediating electron transfer, as expected from the near orthogonality of the porphyrin and substituent rings. This is the first systematic study of electron transfer in porphyrin-donor complexes.

  DOI：

  10.1021/j100137a021

文献信息

• Directed Amination of Aryl Methyl Ethers Mediated by Ti(NMe₂)₄at Room Temperature
  作者：Zhou Chen、Jinna Liu、Hao Pei、Wei Liu、Yanmei Chen、Jian Wu、Wu Li、Yahong Li

  DOI：10.1021/acs.orglett.5b01229

  日期：2015.7.17

  An efficient C–O amination of aryl methyl ethers has been achieved. This transformation proceeds via imine-directed Ti(IV)-mediated cross-coupling reactions between aryl methyl ethers and Ti(NR2)4 at room temperature, straightforwardly leading to a series of arylamines. This protocol features a wide substrate scope, exclusive regioselectivity, and mild reaction conditions.

  已经实现了芳基甲基醚的有效C-O胺化反应。这种转变是通过在室温下亚甲基定向的Ti（IV）介导的芳基甲基醚与Ti（NR 2）4之间的交叉偶联反应进行的，直接导致了一系列芳基胺的出现。该方案具有广泛的底物范围，独特的区域选择性和温和的反应条件。
• Photoinduced Energy- and Electron-Transfer Processes within Dynamic Self-assembled Donor−Acceptor Arrays
  作者：Michael Kercher、Burkhard König、Harald Zieg、Luisa De Cola

  DOI：10.1021/ja026695g

  日期：2002.9.1

  formation. Intercomponent photoinduced energy transfer or electron transfer within the dynamic assembly, which yields to a statistical library of donor-acceptor systems, is reported. The assemblies for energy-transfer processes are constituted by an energy donor, Ru(bpy)(3)(2+)-based component (bpy = 2,2'-bipyridine), and by an energy-acceptor moiety, anthracene-based unit, both substituted with a chelating

  报道了一系列非共价组装的供体-受体系统二元组的合成和光物理特性。所提出的方法使用“无害”配位化合物，乙酰丙酮钪 (III) 衍生物，作为二元形成的核心和促进剂。据报道，动态组件内的组件间光致能量转移或电子转移产生了供体-受体系统的统计库。能量转移过程的组件由能量供体 Ru(bpy)(3)(2+) 基组分（bpy = 2,2'-联吡啶）和能量受体部分构成，基于蒽单位，两者都被螯合配体乙酰丙酮取代，通过与钪离子的配位将确保二元组的形成。如果 N,N,N'N'-四甲基-2，使用 5-二氨基苄基取代的乙酰丙酮配体代替 9-酰基-蒽，从氨基衍生物（电子供体）到 Ru(bpy)(3)(2+)-单元的分子内光诱导电子转移被检测到自组装，由钪复合物介导。光物理过程可以研究动力学不稳定复合物的寿命。