N1,N3,N5-tris(2-hydroxy-1-phenylethyl)benzene-1,3,5-tricarboxamide | 365280-03-1

• 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: N1,N3,N5-tris(2-hydroxy-1-phenylethyl)benzene-1,3,5-tricarboxamide
• 英文别名: 1-N,3-N,5-N-tris[(1R)-2-hydroxy-1-phenylethyl]benzene-1,3,5-tricarboxamide
• CAS: 365280-03-1
• 化学式: C₃₃H₃₃N₃O₆
• 分子量: 567.642
• InChiKey: OTGMXZDGLLARQR-DTXPUJKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  42
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  148
• 氢给体数：
  6
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N1,N3,N5-tris(2-hydroxy-1-phenylethyl)benzene-1,3,5-tricarboxamide 在 甲基磺酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 30.0h， 以95%的产率得到1,3,5-tris[2-(4-(R)-phenyl-1,3-oxazoline)]benzene
  参考文献：
  名称：

  Sugar recognition by C3-symmetric oxazoline hosts

  摘要：

  C-3-Symmetric tris(oxazoline) derivatives (2S,2R) were designed to complex sugars and alcohols in nonpolar organic solvent through complementary intermolecular hydrogen-bonding interactions. H-1 NMR titration demonstrated that the C-3-symmetric hosts were capable of anomer-selective recognition for n-octyl-D-glucopyranoside. H-1 NMR data revealed intermolecular hydrogen bonds between 2S and glucopyranosides. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00915-7
• 作为产物：
  描述：

  均苯三甲酸 在 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 生成 N1,N3,N5-tris(2-hydroxy-1-phenylethyl)benzene-1,3,5-tricarboxamide
  参考文献：
  名称：

  Sugar recognition by C3-symmetric oxazoline hosts

  摘要：

  C-3-Symmetric tris(oxazoline) derivatives (2S,2R) were designed to complex sugars and alcohols in nonpolar organic solvent through complementary intermolecular hydrogen-bonding interactions. H-1 NMR titration demonstrated that the C-3-symmetric hosts were capable of anomer-selective recognition for n-octyl-D-glucopyranoside. H-1 NMR data revealed intermolecular hydrogen bonds between 2S and glucopyranosides. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00915-7

文献信息

• Synthesis of new C3 symmetric amino acid- and aminoalcohol-containing chiral stationary phases and application to HPLC enantioseparations
  作者：Jeongjae Yu、Daniel W. Armstrong、Jae Jeong Ryoo

  DOI：10.1002/chir.22766

  日期：2018.1

  We recently reported a new C3‐symmetric (R)‐phenylglycinol N‐1,3,5‐benzenetricarboxylic acid‐derived chiral high‐performance liquid chromatography (HPLC) stationary phase (CSP 1) that demonstrated better results as compared to a previously described N‐3,5‐dintrobenzoyl (DNB) (R)‐phenylglycinol‐derived CSP. Over a decade ago, (S)‐leucinol, (R)‐phenylglycine, and (S)‐leucine derivatives were used as

  我们最近报道了一种新的C3对称（R）-苯基甘氨醇N -1,3,5-苯三甲酸衍生的手性高效液相色谱（HPLC）固定相（CSP 1），与先前描述的结果相比具有更好的结果N -3,5-二硝基苯甲酰（DNB）（R）-苯基甘氨醇衍生的CSP。十多年前，（S）-亮氨酸，（R）-苯甘氨酸和（S）-亮氨酸衍生物被用作基于3,5-DNB的Pirkle型CSP的手性分离原料。在这项研究中，通过结合上述想法和结果，准备了三个新的C3对称CSP（CSP 2、3和4）。在这里，我们描述了新的C3对称CSP（CSP 2–CSP 4）的合成程序和应用。
• Synthesis and Application of C2 and C3 Symmetric (R)-Phenylglycinol-Derived Chiral Stationary Phases
  作者：Jeongjae Yu、Dong Hyun Ryoo、Jung Mi Lee、Jae Jeong Ryoo

  DOI：10.1002/chir.22572

  日期：2016.3

  A C3 symmetric (R)‐phenylglycinol N‐1,3,5‐benzenetricarboxylic acid‐derived chiral stationary phase (CSP) and three C2 symmetric (R)‐phenylglycinol CSPs were newly synthesized using o‐, m‐, and p‐phthaloyl dichlorides. © 2016 Wiley Periodicals, Inc.

  使用邻，间和对苯二甲酰基新合成了一个C3对称（R）-苯基甘氨醇N-1,3,5-苯三羧酸衍生的手性固定相（CSP）和三个C2对称（R）-苯基甘氨醇CSP。二氯化物。©2016 Wiley Periodicals，Inc.
• Self-Assembly of Discrete Homochiral, Helical, Hydrogen-Bonded Nanocages: From Vesicles to Microspheres and Tubules Capable of Gelating Solvents
  作者：Liwei Yan、Ying Xue、Ge Gao、Jingbo Lan、Fan Yang、Xiaoyu Su、Jingsong You

  DOI：10.1002/chem.200902750

  日期：2010.2.15

  the carboxyl of tartaric acids. These hydrogen‐bonded nanocages can spontaneously self‐assemble into spherical vesicles, during which the hydrogen bonding that arises from the hydroxyl groups of tartaric acids plays a crucial issue. The vesicles formed by [(S,S,S)‐1 a}2(2L)3] (3 a) may further evolve into microspheres that gelate organic solvents after being aged at −20 °C for 24 h, and can also be

  手性三-单齿配体的咪唑啉基1 - ç表现出强的倾向，以形成离散的，螺旋形的[2 + 3]纳米笼3（[ 1 2 ⋅2 3 ]）与酒石酸2。圆二色性（CD）光谱和理论计算表明，类似胶囊结构的超分子手性仅由咪唑啉基配体的手性决定，而不由酒石酸决定。咪唑啉基配体的手性通过咪唑啉环的N 3原子与酒石酸的羧基之间的定向氢键转移至配合物的螺旋。这些氢键结合的纳米笼可以自组装成球形囊泡，在此期间，酒石酸的羟基产生的氢键起着至关重要的作用。由[（S，S，S）-1 a } 2（2 L）3形成的囊泡]（3a）可进一步发展成微球，该微球在-20℃下老化24小时后会凝胶化有机溶剂，并且还可以空前地转变成能够在经受超声波辐射时使溶剂硬化的管状组件。
• A Convenient One-Pot Synthesis of Arene-Centered Tris(thiazoline) Compounds
  作者：Bin Fu、Xuhong Lu、Qingqing Qi、Yumei Xiao、Nan Li

  DOI：10.3987/com-08-11586

  日期：——

  A simple and practical one-pot synthesis of novel enantiopure tris(thiazoline) compounds was documented. The desired products were obtained in moderate to good yields through three steps from commercially available 1, 3, 5-benzenetricarboxylic acid or 2, 4, 6-pyridinetricarboxylic acid, and chiral amino alcohols. Only one column chromatographic purification was needed for the three steps.
• Sugar recognition by C3-symmetric oxazoline hosts
  作者：Hae-Jo Kim、Yeon-Hwan Kim、Jong-In Hong

  DOI：10.1016/s0040-4039(01)00915-7

  日期：2001.7

  C-3-Symmetric tris(oxazoline) derivatives (2S,2R) were designed to complex sugars and alcohols in nonpolar organic solvent through complementary intermolecular hydrogen-bonding interactions. H-1 NMR titration demonstrated that the C-3-symmetric hosts were capable of anomer-selective recognition for n-octyl-D-glucopyranoside. H-1 NMR data revealed intermolecular hydrogen bonds between 2S and glucopyranosides. (C) 2001 Elsevier Science Ltd. All rights reserved.