4-[(S)-2-Cyano-7-(4-hydroxy-phenyl)-heptyl]-benzoic acid tert-butyl ester | 136760-27-5

• 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: 4-[(S)-2-Cyano-7-(4-hydroxy-phenyl)-heptyl]-benzoic acid tert-butyl ester
• 英文别名: tert-butyl 4-<(2R)-2-cyano-7-(4-hydroxyphenyl)heptylidene>benzoate
• CAS: 136760-27-5
• 化学式: C₂₅H₃₁NO₃
• 分子量: 393.526
• InChiKey: OHSAJLZGQCVHTI-OAQYLSRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.83
• 重原子数：
  29.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  70.32
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-[(S)-2-Cyano-7-(4-hydroxy-phenyl)-heptyl]-benzoic acid tert-butyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 4-[(R)-2-Cyano-7-(4-hydroxy-phenyl)-heptyl]-benzoic acid
  参考文献：
  名称：

  Materials chemistry of chiral macromolecules. 1. Synthesis and phase transitions

  摘要：

  This paper describes work on synthesis of chiral macromolecules as part of a materials chemistry study which seeks to establish links in these systems among molecular structure, three-dimensional molecular organization, and properties. The basic materials chemistry hypothesis driving this work is that chiral forces among stereogenic centers may serve as guiding fields to organize polymers in two or three dimensions. It follows that physical properties could be directly or indirectly controlled by chirality. In order to promote strong forces among chiral centers the chains were designed to have stereogenic carbons substituted by the strongly dipolar cyano group and spaced by 16 atoms along the backbone. The preparative chemistry of chiral macromolecules is challenging given the limited number of polymerization methodologies and the inherent translational periodicity of synthetic polymers. We have synthesized here low symmetry chiral macromolecules in which the only symmetry element retained is polar translation; achiral homologues lacking the nitrile function, the configurationally disordered polymer, and dimeric model compounds were prepared as well. The compounds exhibited crystalline and liquid crystalline phases, and significant differences were observed among homologues through differential scanning calorimetry and optical microscopy. The substitution of nitrile groups every 16 atoms along the polymer backbone, specially with configurational disorder, leads to glassy or less ordered condensed phases. In some Polymers when the strongly dipolar stereogenic centers do not have preferred handedness, chains organize into mesophases rather than crystalline structures. This is surprising since the concentration of stereogenic centers is extremely dilute. Using dimeric model compounds, homochiral recognition among stereogenic centers with large dipole moments was identified as an important factor in the assembly of molecules into layered structures. Interestingly, catenation of the dipolar stereogenic centers in polymeric compounds apparently leads to layered structures even when configurational disorder exists along the polymer backbone. This type of structural control could be extremely useful as an approach to tune physical properties of polymeric materials.

  DOI：

  10.1021/ja00035a041
• 作为产物：
  描述：

  4-((S)-2-Cyano-7-{4-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-phenyl}-heptyl)-benzoic acid tert-butyl ester 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以100%的产率得到4-[(S)-2-Cyano-7-(4-hydroxy-phenyl)-heptyl]-benzoic acid tert-butyl ester
  参考文献：
  名称：

  二维聚合物的批量合成：分子识别方法

  摘要：

  这份手稿描述了使用刚性前体分子自组装成双层的形状持久二维 (2D) 聚合物的批量合成。合成了一种前体，其结构编码必要的分子识别事件，以形成具有内部取向顺序的双层。这些事件包括同手性相互作用并将反应功能限制在平面上，从而导致扁平聚合物的共价拼接。所得分子物体具有 5 nm 的单分散厚度和数百或数千纳米数量级的多分散平面尺寸。拼接反应之一，丙烯酸酯基团低聚形成全碳主链，是由距离双键 13 个原子的偶极立构中心催化的。这些富含对映体的立体中心被腈基取代，腈基反应生成板状分子的第二个缝合骨架。计算机模拟表明，如果通过分子识别事件实现功能的平面限制，则可以形成具有极短拼接主链的摩尔质量在数百万范围内的二维聚合物。不需要外部边界将单体限制在 2D 空间中的形状持久性 2D 聚合物的“批量”合成可能会产生许多有趣的先进材料。35 个参考文献，17 个无花果。计算机模拟表明，如果通过分子识别事件实现功能的

  DOI：

  10.1021/ja00124a005