methyl 3,4-bis-[(6-((S)-3,7-dimethyloctyloxy)naphthalen-2-yl)methoxy]-benzoate | 1239597-78-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl 3,4-bis-[(6-((S)-3,7-dimethyloctyloxy)naphthalen-2-yl)methoxy]-benzoate
• CAS: 1239597-78-4
• 化学式: C₅₀H₆₄O₆
• 分子量: 761.055
• InChiKey: MKMNQVNEPLTLQQ-UWXQCODUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.4
• 重原子数：
  56.0
• 可旋转键数：
  23.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 3,4-bis-[(6-((S)-3,7-dimethyloctyloxy)naphthalen-2-yl)methoxy]-benzoate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以88%的产率得到
  参考文献：
  名称：

  Programming the Supramolecular Helical Polymerization of Dendritic Dipeptides via the Stereochemical Information of the Dipeptide

  摘要：

  Many natural biomacromolecules are homochiral and are built from constituents possessing identical handedness. The construction of synthetic molecules, macromolecules, and supramolecular structures with tailored stereochemical sequences can detail the relationship between chirality and function and provide insight into the process that leads to the selection of handedness and amplification of chirality. Dendritic dipeptides, previously reported from our laboratory, self-assemble into helical porous columns and serve as fundamental mimics of natural porous helix-forming proteins and supramolecular polymers. Herein, the synthesis of all stereochemical permutations of a self-assembling dendritic dipeptide including homochiral, heterochiral, and differentially racemized variants is reported. A combination of CD/UV-vis spectroscopy in solution and in film, X-ray diffraction, and differential scanning calorimetry studies in solid state established the role of the stereochemistry of the dipeptide on the thermodynamics and mechanism of self-assembly. It was found that the highest degree of stereochemical purity, enantiopure homochiral dendritic dipeptides, exhibits the most thermodynamically favorable self-assembly process in solution corresponding to the greatest degree of helical order and intracolumnar crystallization in solid state. Reducing the stereochemical purity of the dendritic dipeptide through heterochirality or by partially or fully racernizing the dendritic dipeptide destructively interferes with the self-assembly process. All dendritic dipeptides were shown to coassemble into single columns regardless of their stereochemistry. Because these columns exhibit no deracemization, the thermodynamic advantage of enantiopurity and homochirality suggests a mechanism for stereochemical selection and chiral amplification.

  DOI：

  10.1021/ja200280h
• 作为产物：
  描述：

  3,4-二羟基苯甲酸甲酯 、 (S)-2-(chloromethyl)-6-(3,7-dimethyloctyloxy)naphthalene 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以83%的产率得到methyl 3,4-bis-[(6-((S)-3,7-dimethyloctyloxy)naphthalen-2-yl)methoxy]-benzoate
  参考文献：
  名称：

  杂化树突自组装成双重分离的超分子多面体柱和囊泡

  摘要：

  报道了从包含 20 个第一代杂化树突的 3 个库中自组装的超分子树枝状聚合物的合成和结构分析。苄基醚、萘基甲基醚和联苯甲基醚重复单元与树枝顶端不同的烷基羧酸盐的组合将其分子立体角降低到导致发现新自组装机制的值。这种新的自组装机制产生了前所未有的超分子组装的多样性，包括空心和非空心的单或双隔离的超分子柱和呈现多面体形状的囊泡。自组织超分子树枝状聚合物的多面体形状被证明是所有双重分离结构的内在特征。

  DOI：

  10.1021/ja104432d