3,4,5-tris(dodecanyloxy)-N-(2-hydroxyethyl)benzamide | 257946-98-8

• 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: 3,4,5-tris(dodecanyloxy)-N-(2-hydroxyethyl)benzamide
• 英文别名: N-[3,4,5-tris(n-dodecan-1-yloxy)benzoyl]-2-aminoethanol；3,4,5-tridodecoxy-N-(2-hydroxyethyl)benzamide
• CAS: 257946-98-8
• 化学式: C₄₅H₈₃NO₅
• 分子量: 718.158
• InChiKey: OWSZRUMSJFADMU-UHFFFAOYSA-N

物化性质

• 沸点：
  743.3±60.0 °C(Predicted)
• 密度：
  0.944±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  17.2
• 重原子数：
  51
• 可旋转键数：
  39
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  77
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,4,5-tris(dodecanyloxy)-N-(2-hydroxyethyl)benzamide 在 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 N-[3,4,5-tris(n-dodecan-1-yloxy)phenyl]-2-oxazoline
  参考文献：
  名称：

  Spherical Supramolecular Minidendrimers Self-Organized in an “Inverse Micellar”-like Thermotropic Body-Centered Cubic Liquid Crystalline Phase

  摘要：

  An "inverse micellar"- or "water-in-oil"-like (similar to the lyotropic type I-II) thermotropic body-centered cubic (BCC) liquid crystal (LC) phase was discovered in a poly(ethyleneimine) with a degree of polymerization (DP) = 20 containing 3,3,5-tri(dodecyloxy)benzoyl minidendritic side groups. Fiber X-ray diffraction (XRD) experiments show that the extinction symbol of this phase is I--- and, alongside other evidence, suggested that the space group is Im (3) over bar m (Q(229)). These results point to a supramolecular inverse micellar-like structure with the polymer backbone and the benzoyl groups aggregated into globules located at the corners and the center of the unit cell. The n-alkyl groups radiate out of the aromatic part of the globule: and make up the continuos matrix of the lattice. The cubic unit cell parameter is a = 42.6 Angstrom. Upon shearing, the BCC phase aligns along the [111] direction. The BCC lyotropic Im (3) over bar m inverse micellar phase of I-II type has not yet been observed and the experiments reported here will access its design. The present is only the second "inverse micellar" thermotropic LC phase known. The first one was previously reported from our laboratories (Balagurusamy, V. S. K.; Ungar, G.; Percec, V.; Johansson, G. J. Am. Chem. Soc, 1997, 119, 1539) and has a Pm (3) over bar n symmetry. Both the Im (3) over bar m and the Pm (3) over bar n cubic lattices were self-organized from spherical supramolecular dendrimers. The BCC cubic LC lattice reported hen enriches the synthetic capabilities of dendritic building blocks.

  DOI：

  10.1021/ja993915q
• 作为产物：
  描述：

  苯甲酸,3,4,5-三(十二烷氧基)- 在 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.5h， 生成 3,4,5-tris(dodecanyloxy)-N-(2-hydroxyethyl)benzamide
  参考文献：
  名称：

  Spherical Supramolecular Minidendrimers Self-Organized in an “Inverse Micellar”-like Thermotropic Body-Centered Cubic Liquid Crystalline Phase

  摘要：

  An "inverse micellar"- or "water-in-oil"-like (similar to the lyotropic type I-II) thermotropic body-centered cubic (BCC) liquid crystal (LC) phase was discovered in a poly(ethyleneimine) with a degree of polymerization (DP) = 20 containing 3,3,5-tri(dodecyloxy)benzoyl minidendritic side groups. Fiber X-ray diffraction (XRD) experiments show that the extinction symbol of this phase is I--- and, alongside other evidence, suggested that the space group is Im (3) over bar m (Q(229)). These results point to a supramolecular inverse micellar-like structure with the polymer backbone and the benzoyl groups aggregated into globules located at the corners and the center of the unit cell. The n-alkyl groups radiate out of the aromatic part of the globule: and make up the continuos matrix of the lattice. The cubic unit cell parameter is a = 42.6 Angstrom. Upon shearing, the BCC phase aligns along the [111] direction. The BCC lyotropic Im (3) over bar m inverse micellar phase of I-II type has not yet been observed and the experiments reported here will access its design. The present is only the second "inverse micellar" thermotropic LC phase known. The first one was previously reported from our laboratories (Balagurusamy, V. S. K.; Ungar, G.; Percec, V.; Johansson, G. J. Am. Chem. Soc, 1997, 119, 1539) and has a Pm (3) over bar n symmetry. Both the Im (3) over bar m and the Pm (3) over bar n cubic lattices were self-organized from spherical supramolecular dendrimers. The BCC cubic LC lattice reported hen enriches the synthetic capabilities of dendritic building blocks.

  DOI：

  10.1021/ja993915q

文献信息

• Thermodynamics of the Helical, Supramolecular Polymerization of Linear Self-Asembling Molecules: Influence of Hydrogen Bonds and π Stacking
  作者：Fátima Aparicio、Luis Sánchez

  DOI：10.1002/chem.201300553

  日期：2013.8.5

  The cooperative supramolecular polymerization of 1 and 2 show very similar thermodynamic parameters (Δ, ΔS0, and Δ), but very different organization of the self‐assembling units to constitute helical structures. The results presented allow the quantification of the influence of the type and number of non‐covalent interactions in supramolecular polymerization.

  1和2的合作超分子聚合显示出非常相似的热力学参数（Δ ，ΔS 0和Δ ），但是自组装单元构成螺旋结构的组织却非常不同。给出的结果可以量化超分子聚合中非共价相互作用的类型和数量的影响。
• Pathway Complexity Versus Hierarchical Self‐Assembly in <i>N</i> ‐Annulated Perylenes: Structural Effects in Seeded Supramolecular Polymerization
  作者：Elisa E. Greciano、Beatriz Matarranz、Luis Sánchez

  DOI：10.1002/anie.201801575

  日期：2018.4.16

  Studies were carried out on the hierarchical self‐assembly versus pathway complexity of N‐annulated perylenes 1–3, which differ only in the nature of the linking groups connecting the perylene core and the side alkoxy chains. Despite the structural similarity, compounds 1 and 2 exhibit noticeable differences in their self‐assembly. Whereas 1 forms an off‐pathway aggregate I that converts over time

  研究，在N个-环苝的层次自组装与途径的复杂性进行1 - 3，不同之处仅在连接苝芯和烷氧基链的一侧的连接基团的性质。尽管结构相似，化合物1和2在自组装方面仍表现出明显的差异。而1种形式的偏离路径集合体我，其将随时间（或通过添加种子的）转换成热力学上途径产物，2所经历分级方法，其中动力学捕获单体种类不会导致动力学控制的超分子的增长。最后，化合物3缺少酰胺基的烷烃在相同的实验条件下无法自组装，并突出了酰胺基的关键相关性及其在支配自组装途径中的位置。
• Biasing the Hierarchy Motifs of Nanotoroids: from 1D Nanotubes to 2D Porous Networks
  作者：Jorge S. Valera、Hironari Arima、Cristina Naranjo、Takuho Saito、Natsuki Suda、Rafael Gómez、Shiki Yagai、Luis Sánchez

  DOI：10.1002/anie.202114290

  日期：2022.1.26

  reported azobenzene dyads impedes their hierarchical self-assembly from nanotoroids into nanotubes. In contrast, they organize into 2D porous networks on substrate upon solution processing. Photoisomerization of azobenzene moieties allows efficient dissociation/reorganization of nanotoroids in solution, demonstrating their potential as photoresponsive 2D porous nanosheets.

  所报道的偶氮苯二联体的外围侧链所施加的空间需求阻碍了它们从纳米环形物到纳米管的分层自组装。相比之下，它们在溶液处理后在基材上组织成二维多孔网络。偶氮苯部分的光异构化允许纳米环在溶液中有效解离/重组，证明了它们作为光响应二维多孔纳米片的潜力。
• Holerca, Marian N.; Percec, Virgil, European Journal of Organic Chemistry, 2000, # 12, p. 2257 - 2263
  作者：Holerca, Marian N.、Percec, Virgil

  DOI：——

  日期：——
• Spherical Supramolecular Minidendrimers Self-Organized in an “Inverse Micellar”-like Thermotropic Body-Centered Cubic Liquid Crystalline Phase
  作者：Duncan J. P. Yeardley、Goran Ungar、Virgil Percec、Marian N. Holerca、Gary Johansson

  DOI：10.1021/ja993915q

  日期：2000.3.1

  An "inverse micellar"- or "water-in-oil"-like (similar to the lyotropic type I-II) thermotropic body-centered cubic (BCC) liquid crystal (LC) phase was discovered in a poly(ethyleneimine) with a degree of polymerization (DP) = 20 containing 3,3,5-tri(dodecyloxy)benzoyl minidendritic side groups. Fiber X-ray diffraction (XRD) experiments show that the extinction symbol of this phase is I--- and, alongside other evidence, suggested that the space group is Im (3) over bar m (Q(229)). These results point to a supramolecular inverse micellar-like structure with the polymer backbone and the benzoyl groups aggregated into globules located at the corners and the center of the unit cell. The n-alkyl groups radiate out of the aromatic part of the globule: and make up the continuos matrix of the lattice. The cubic unit cell parameter is a = 42.6 Angstrom. Upon shearing, the BCC phase aligns along the [111] direction. The BCC lyotropic Im (3) over bar m inverse micellar phase of I-II type has not yet been observed and the experiments reported here will access its design. The present is only the second "inverse micellar" thermotropic LC phase known. The first one was previously reported from our laboratories (Balagurusamy, V. S. K.; Ungar, G.; Percec, V.; Johansson, G. J. Am. Chem. Soc, 1997, 119, 1539) and has a Pm (3) over bar n symmetry. Both the Im (3) over bar m and the Pm (3) over bar n cubic lattices were self-organized from spherical supramolecular dendrimers. The BCC cubic LC lattice reported hen enriches the synthetic capabilities of dendritic building blocks.