2-hydroxy-N-(thiophen-2-ylmethyl)benzamide | 91569-39-0

• 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-hydroxy-N-(thiophen-2-ylmethyl)benzamide
• 英文别名: N-(2-thienylmethyl)salicylamide；2-thenylsalicylamide；thenylsalicylamide；(C₄H₃S)CH₂NHC(O)(C₆H₄)OH；2-hydroxy-N-thiophen-2-ylmethyl-benzamide；2-Hydroxy-benzoesaeure-
• CAS: 91569-39-0
• 化学式: C₁₂H₁₁NO₂S
• mdl: MFCD01566147
• 分子量: 233.291
• InChiKey: XTDYYXLPYSQGGZ-UHFFFAOYSA-N

物化性质

• 熔点：
  155.5-156 °C
• 沸点：
  460.3±35.0 °C(Predicted)
• 密度：
  1.307±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.083
• 拓扑面积：
  77.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-hydroxy-N-(thiophen-2-ylmethyl)benzamide 在 potassium carbonate 作用下， 以 甲醇 、 乙酸乙酯 、 丙酮 为溶剂， 反应 347.0h， 生成 [Tb₂(NO₃)₆(1,4-bis{[(2′-thenylaminoformyl)phenoxyl]methyl}-2,5-bismethylbenzene₎₃]_∞
  参考文献：
  名称：

  Lanthanide coordination polymers constructed by a new semirigid bridging salicylamide ligand: Synthesis, structure and luminescence properties

  摘要：

  A new semirigid exo-bidentate ligand incorporating thenylsalicylamide terminal groups, namely 1,4-bis{[(2'-thenylaminoformyl) phenoxyl] methyl}-2,5-bismethylbenzene was synthesized and used as building blocks for constructing lanthanide coordination polymers with luminescent properties. The series of lanthanide nitrate complexes have been characterized by elemental analysis, IR spectroscopy, and X-ray diffraction analysis. All the lanthanide coordination polymers exhibit the same metal-to-ligand molar ratio of 2: 3 and the semirigid exo-bidentate ligand as a bridging ligand, reacts with lanthanide nitrates forming 1D annular chains {[Ln2(NO3)(6)L-3](infinity) (Ln = Nd (1), Sm (2), Eu (3), Tb (4)}. The samarium, europium and terbium containing compounds exhibit luminescence of the referring trivalent lanthanide ions, giving an orange luminescence for SmIII, a red luminescence for EuIII and a green luminescence for TbIII triggered by an efficient antenna effect of the thenylsalicylamide group. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2013.08.014
• 作为产物：
  描述：

  2-噻吩甲醛 、 水杨酰胺 在 dicobalt octacarbonyl 、 氢气 、 三(对甲苯基)锑 作用下， 以 四氢呋喃 为溶剂， 120.0 ℃ 、4.48 MPa 条件下， 反应 24.0h， 以51%的产率得到2-hydroxy-N-(thiophen-2-ylmethyl)benzamide
  参考文献：
  名称：

  One-pot stibine modified Co2(CO)8 catalyzed reductive N-alkylation of primary amides with carbonyl compounds

  摘要：

  A one-pot stibine modified Co-2(CO)(8) homogeneous catalytic reductive N-alkylation of primary amides using aldehydes/ketones as alkylating agents, is reported. Good to excellent yields of a wide range of secondary amides are obtained (up to 97%) under relative mild conditions. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.01.038

文献信息

• Synthesis, crystal structure and luminescence properties of lanthanide coordination polymers with a new semirigid bridging thenylsalicylamide ligand
  作者：Xue-Qin Song、Li Wang、Meng-Meng Zhao、Xiao-Run Wang、Yun-Qiao Peng、Guo-Quan Cheng

  DOI：10.1016/j.jssc.2013.07.014

  日期：2013.9

  Two new lanthanide coordination polymers based on a semirigid bridging thenylsalicylamide ligand [Ln2L3(NO3)6]·(C4H8O2)2}∞ were obtained and characterized by elemental analysis, X-ray diffraction, IR and TGA measurements. The two compounds are isostructure and possess one dimensional trapezoid ladder-like chain built up from the connection of isolated LnO3(NO3)3 polyhedra (distorted monocapped antisquare

  基于两个新的镧系元素配位聚合物的半刚性桥接thenylsalicylamide配体[LN 2大号3（NO 3）6 ]·（C 4 H ^ 8 ö 2）2 } ∞获得和表征通过元素分析，X射线衍射，IR和TGA测量。两种化合物等结构，并具有一个维梯形阶梯状从连接建立链分离LNO 3（NO 3）3多面体通过配体（扭曲单封antisquare棱镜）。光致发光分析表明，在Tb（III）络合物中存在有效的配体到Ln（III）的能量转移，并且配体是Tb（III）的有效“天线”。从更一般的观点来看，本文证明的结果提供了控制所需镧系元素配位结构的形成以丰富晶体工程策略并扩大用于开发优异的发光镧系元素配位聚合物的砷的可能性。
• Synthesis and Crystal Structure of 1,4-bis{[(2'-Thenylaminoformyl)phenoxyl]methyl}benzene
  作者：Li Wang、Xiao-Run Wang、Guo-Quan Cheng、Yun-Qiao Peng、Xue-Qin Song

  DOI：10.14233/ajchem.2013.16062

  日期：——

  A novel salicylamide derivative i.e., 1,4-bis[(2-thenylaminoformyl)phenoxyl]methyl}benzene with the m.f. C32H28N2O4S2 has been synthesized and the crystal structure was determined by single crystal X-ray diffraction. There are strong intramolecular hydrogen bonding between the amide nitrogen atoms and the ethereal oxygen atoms which stabilized the structure to form a trans configuration. Furthermore the title compound are linked by intermolecular C9-H9…O1 hydrogen bonds into an infinite 1D chain parallel to the bc plane .

  我们合成了一种新型水杨酰胺衍生物，即 1,4-双[(2-苯氨基甲酰基)苯氧基]甲基}苯，其分子式为 C32H28N2O4S2，并通过单晶 X 射线衍射确定了其晶体结构。酰胺氮原子和乙醚氧原子之间存在很强的分子内氢键，从而稳定了结构，形成了反式构型。此外，标题化合物通过分子间 C9-H9...O1 氢键连接成平行于 bc 平面的无限一维链。
• Synthesis, crystal structure and luminescence properties of homodinuclear lanthanide complexes with a new tetrapodal thenylsalicylamide ligand
  作者：Xue-Qin Song、Li Wang、Meng-Meng Zhao、Guo-Quang Cheng、Xiao-Run Wang、Yun-Qiao Peng

  DOI：10.1016/j.ica.2013.03.040

  日期：2013.6

  Five new homodinuclear lanthanide(III) complexes with a new tetrapodal thenylsalicylamide ligand (L), of formulae [Nd2L2(NO3)(6)(CH3OH)(2)]center dot 2H(2)O center dot 2CH(3)OH (1), and [Ln(2)L(2)(NO3)(6) (CH3OH)(2)]center dot 4CH(3)OH, Ln = Sm (2), Eu (3), Gd (4), Tb (5)) have been synthesized and characterized by single-crystal X-ray diffraction, elemental analysis, IR spectroscopy and molar conductance analysis. The two arms of L ligand arranged in a complementary head to head fashion to bind two lanthanide to form a cage-like coordination dimer with the other two uncoordinated arms constructing interesting three dimensional supramolecular structures. The europium and terbium containing compounds both exhibit luminescence of the referring trivalent lanthanide ions, giving a red luminescence for Eu(III) and a green luminescence for Tb(III) triggered by an efficient antenna effect of the thenylsalicylamide group. (C) 2013 Elsevier B.V. All rights reserved.
• Berner, Joachim; Boehland, Heinz; Werner, Manfred, Zeitschrift fur Chemie, 1987, vol. 27, p. 61 - 62
  作者：Berner, Joachim、Boehland, Heinz、Werner, Manfred、Richter, Thomas

  DOI：——

  日期：——
• One-pot stibine modified Co2(CO)8 catalyzed reductive N-alkylation of primary amides with carbonyl compounds
  作者：Laura Rubio-Pérez、Pankaj Sharma、F. Javier Pérez-Flores、Luis Velasco、J. Luis. Arias、Armando Cabrera

  DOI：10.1016/j.tet.2012.01.038

  日期：2012.3

  A one-pot stibine modified Co-2(CO)(8) homogeneous catalytic reductive N-alkylation of primary amides using aldehydes/ketones as alkylating agents, is reported. Good to excellent yields of a wide range of secondary amides are obtained (up to 97%) under relative mild conditions. (C) 2012 Elsevier Ltd. All rights reserved.