1,1'-binaphthalene-2,2',6,6'-tetracarboxylic acid | 860650-55-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,1'-binaphthalene-2,2',6,6'-tetracarboxylic acid
• 英文别名: 1-(2,6-Dicarboxynaphthalen-1-yl)naphthalene-2,6-dicarboxylic acid；1-(2,6-dicarboxynaphthalen-1-yl)naphthalene-2,6-dicarboxylic acid
• CAS: 860650-55-1；860781-94-8；860781-95-9
• 化学式: C₂₄H₁₄O₈
• 分子量: 430.37
• InChiKey: ZJROUSBPKWQHJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  149
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  dimethyl 1-bromonaphthalene-2,6-dicarboxylate 在 吡啶 、 4-二甲氨基吡啶 、 氢氧化钾 、 sodium hydroxide 、 氯化亚砜 、 铜 、 N,N-二甲基甲酰胺 作用下， 以 甲醇 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 29.5h， 生成 1,1'-binaphthalene-2,2',6,6'-tetracarboxylic acid
  参考文献：
  名称：

  Interpenetrating chiral 2D grid nets: hetero- versus homochiral 3D polycatenation in the crystal self-assembly of (RS)- and (R)-1,1′-binaphthalene-2,2′,6,6′-tetracarboxylic acids

  摘要：

  Crystallographic analysis of the title binaphthyl tetracid 2 revealed unique propensity to polycatenation upon crystallization of both the enantiomerically homogeneous as well as the racemic form of the axially chiral tecton. Stereochemical aspects of the polycateriation have been analyzed in three Conceptual steps, (i) formation of infinite 2D grids set up from hydrogen-bonded tecton cyclotetramers, (ii) stacking of the 2D grids, and (iii) interpenetration of the resulting stacks. In the crystal self-assembly of the enantiomerically uniform tecton, all three steps are homochiral. Conversely, in the crystal of the racemic tecton the homochiral self-assembling algorithm operates only in the steps (i) and (ii), giving rise to separate, antipodal, stacks of homochiral 2D layers. In the final step (iii), the antipodal stacks mutually interpenetrate, yielding racemic 3D polycatenated architecture within a single crystal. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.04.018

文献信息

• Interpenetrating chiral 2D grid nets: hetero- versus homochiral 3D polycatenation in the crystal self-assembly of (RS)- and (R)-1,1′-binaphthalene-2,2′,6,6′-tetracarboxylic acids
  作者：Petr Holý、Martin Kováč、Miloš Tichý、Jiří Závada、Miloš Buděšínský、Ivana Císařová

  DOI：10.1016/j.tetasy.2005.04.018

  日期：2005.6

  Crystallographic analysis of the title binaphthyl tetracid 2 revealed unique propensity to polycatenation upon crystallization of both the enantiomerically homogeneous as well as the racemic form of the axially chiral tecton. Stereochemical aspects of the polycateriation have been analyzed in three Conceptual steps, (i) formation of infinite 2D grids set up from hydrogen-bonded tecton cyclotetramers, (ii) stacking of the 2D grids, and (iii) interpenetration of the resulting stacks. In the crystal self-assembly of the enantiomerically uniform tecton, all three steps are homochiral. Conversely, in the crystal of the racemic tecton the homochiral self-assembling algorithm operates only in the steps (i) and (ii), giving rise to separate, antipodal, stacks of homochiral 2D layers. In the final step (iii), the antipodal stacks mutually interpenetrate, yielding racemic 3D polycatenated architecture within a single crystal. (c) 2005 Elsevier Ltd. All rights reserved.