2,3-dihydroxy-ethylterephthalamide | 117918-05-5

• 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: 2,3-dihydroxy-ethylterephthalamide
• 英文别名: N,N'-diethyl-2,3-dihydroxyterephthalamide；etTAM；1,4-Benzenedicarboxamide, N,N'-diethyl-2,3-dihydroxy-；1-N,4-N-diethyl-2,3-dihydroxybenzene-1,4-dicarboxamide
• CAS: 117918-05-5
• 化学式: C₁₂H₁₆N₂O₄
• 分子量: 252.27
• InChiKey: DUSJXDOHVDQOBK-UHFFFAOYSA-N

物化性质

• 沸点：
  412.9±45.0 °C(Predicted)
• 密度：
  1.261±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  98.7
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  bis(acetylacetonate)oxovanadium 、 2,3-dihydroxy-ethylterephthalamide 在 KOH 作用下， 以 甲醇 、 乙醇 为溶剂， 生成
  参考文献：
  名称：

  Karpishin, Timothy B.; Stack; Raymond, Kenneth N., Journal of the American Chemical Society, 1993, vol. 115, # 1, p. 182 - 192

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3-二羟基对苯二甲酸 、 乙胺 在 氯化亚砜 、 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 6.0h， 生成 2,3-dihydroxy-ethylterephthalamide
  参考文献：
  名称：

  A Streamlined Synthesis for 2,3-Dihydroxyterephthalamides

  摘要：

  [GRAPHICS]2,3-Dihydroxyterephthalamides have been synthesized through a route that avoids the protection and deprotection of the phenol groups. The procedure allows for symmetric and unsymmetric amide linkages. This synthetic sequence significantly decreases the time and cost of preparation and increases the overall yield of this class of metal chelators.

  DOI：

  10.1021/ol016253u

文献信息

• Titanium(IV) Complexes with <i>N</i>,<i>N</i>′-Dialkyl-2,3-dihydroxyterephthalamides and 1-Hydroxy-2(1<i>H</i>)-pyridinone as Siderophore and Tunichrome Analogues
  作者：Ritika Uppal、Hayley P. Israel、Christopher D. Incarvito、Ann M. Valentine

  DOI：10.1021/ic901177c

  日期：2009.11.16

  of Ti(IV) with biological ligands siderophores and tunichromes is modeled by using N,N′-dialkyl-2,3-dihydroxyterephthalamides (alTAMs), analogues of catecholamide-containing biomolecules, and 1-hydroxy-2(1H)-pyridinone (1,2-HOPO), an analogue of hydroxamate-containing biomolecules. Both types of ligands stabilize Ti(IV) with respect to hydrolytic precipitation, and afford tractable complexes. Complexes

  通过使用N，N'-二烷基-2,3-二羟基对苯二甲酰胺（alTAMs），含儿茶酚酰胺的生物分子类似物和1-hydroxy-2（1 H）来模拟具有生物配体铁载体和单色染料的Ti（IV）的水化学）-吡啶酮（1,2-HOPO），一种含异羟肟酸酯的生物分子类似物。两种类型的配体都相对于水解沉淀稳定Ti（IV），并提供易于处理的络合物。与alTAM的甲基衍生物meTAM形成的复合物通过质谱和UV / vis光谱进行表征。具有etTAM的复合物通过相同的技术以及X射线晶体学，循环伏安法和分光电位滴定法进行表征。这些络合物在水中的ESI质谱显示金属/配体种类为1：2和1：3。1：2络合物K 2 [Ti（etTAM）2（OCH 3）2 ]·2CH 3 OH（1的X射线晶体结构），被报告。溶解在溶液中的1还原的中点电位为-0.98V。Ti / etTAM 1：3物种的结构Na 2 [Ti（etTAM）3 ]证
• Characterization of 2,3-Dihydroxyterephthalamides as M(IV) Chelators¹
  作者：Christine J. Gramer、Kenneth N. Raymond

  DOI：10.1021/ic0496267

  日期：2004.10.1

  The ligand N,N'-diethyl-2,3-dihydroxyterephthalamide (ETAM) has been characterized as a chelator for Zr(IV), Ce(IV), and Th(IV). The K+ salts of the complexes [Zr(ETAM)(4)](4-), [Ce(ETAM)(4)](4-), and [Th(ETAM)(4)](4-) were prepared in a MeOH solution containing H(2)ETAM, the corresponding M(acac)(4), and 4 equiv of KOH. Single-crystal X-ray diffraction analyses are reported for K-4[Zr(ETAM)(4)] (C2/c, Z = 8, a = 27.576(3) Angstrom, b = 29.345(3) Angstrom, c = 15.266(2) Angstrom, alpha = 90degrees, beta = 118.688(4)degrees, gamma = 90degrees), [Me3BnN](4)[Th(ETAM)(4)] (P (1) over bar, Z = 2, a = 13.7570(3) Angstrom, b = 13.9293(3) Angstrom, c = 26.9124(6) Angstrom, alpha = 99.941(1)degrees, beta = 94.972(1)degrees, gamma = 103.160(1)degrees), and the dimeric (NMe4)(4)[Th(ETAM)(3)MeOH](2) (P2(1)/c, Z = 4, a = 18.2603(9) Angstrom, b = 18.5002(9) Angstrom, c = 19.675(1) Angstrom, beta = 117.298(1)degrees). Solution thermodynamic studies were used to determine formation constants (log K-1 and esd) for Th(IV)-ETAM log K-110 =17.47(1), log K-120 = 13.23(1), log K-130 = 8.28(3), log K-140 = 6.57(6), and log beta(140) = 45.54(5). These results support the hypothesis that the terephthalamides are high-affinity chelators for the actinide(IV) ions and thus promising ligands for use in nuclear waste remediation.
• Spectroscopic studies of the electronic structure of iron(III) tris(catecholates)
  作者：Timothy B. Karpishin、Matthew S. Gebhard、Edward I. Solomon、Kenneth N. Raymond

  DOI：10.1021/ja00008a028

  日期：1991.4

  Single-crystal polarized absorption and magnetic circular dichroism (MCD) have been employed to elucidate the electronic structure of the iron(III) tris(catecholate) complex [Fe(cat)3]3- to investigate the bonding in ferric enterobactin and similar catechol siderophores. In addition to [Fe(cat)3]3-, two related complexes, [Fe(TRENCAM)]3-, a catecholamide, and [Fe(eta)3]3-, a terephthalamide, have been studied by MCD to provide a perturbation on the electronic structure of [Fe(cat)3]3- and to also determine differences in bonding between the three complexes. The ligand-to-metal charge-transfer (CT) band characteristic of the catecholate siderophores is found for [Fe(cat)3]3- to be composed of two overlapping x,y polarized transitions at 18414 and 22018 cm-1. These transitions are ligand pi-to metal d in nature; assignments of these and four other CT transitions and an experimental energy order for the molecular orbitals of the complexes are made in D3 symmetry. It is evident from analysis of the spectra that a significant contribution to the Fe-O interaction in these complexes is made by pi-bonding. An estimate of 10Dq as approximately 13 000 cm-1 is made for the iron(III) tris(catecholates) from the transition energy of the spin forbidden ligand field (LF)6A1 --> 4T1 transition observed in the MCD. A value of 10Dq is also obtained from the CT transition energies and is determined to be approximately 63% of the value obtained from the LF transitions. This reduction indicates that the CT excited state is best described as an iron(II) species. Analysis of the CT spectra indicates that the electronic structure of the two complexes [Fe(cat)3]3- and [Fe(TRENCAM)]3- are similar, whereas [Fe(eta)3]3- shows a higher degree of sigma- and pi-interactions in Fe-O bonding. The contribution of differences in bonding to the known thermodynamic stability constants is discussed.
• WASCH- UND REINIGUNGSMITTEL MIT VERBESSERTER LEISTUNG
  申请人：Henkel AG & Co. KGaA

  公开号：EP3218462A1

  公开（公告）日：2017-09-20
• DETERGENT AND CLEANING AGENTS HAVING IMPROVED PERFORMANCE
  申请人：Henkel AG & Co. KGaA

  公开号：US20170240849A1

  公开（公告）日：2017-08-24

  The present invention relates to the use of dihydroxyterephthalic acid derivatives in washing and cleaning agents for improving the washing or cleaning performance with respect to bleachable stains.