dimethyl 1-bromonaphthalene-2,6-dicarboxylate | 165594-79-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: dimethyl 1-bromonaphthalene-2,6-dicarboxylate
• CAS: 165594-79-6
• 化学式: C₁₄H₁₁BrO₄
• 分子量: 323.143
• InChiKey: KOGWCRBEPFRMPA-UHFFFAOYSA-N

物化性质

• 沸点：
  417.2±25.0 °C(Predicted)
• 密度：
  1.499±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  1-bromonaphthalene-2,6-dicarboxylic acid 、 甲醇 在 硫酸 作用下， 反应 48.0h， 以77.9%的产率得到dimethyl 1-bromonaphthalene-2,6-dicarboxylate
  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

• NAPHTHALENEDICARBOXYLIC ACID CONTAINING POLYMER/HALOGEN COMPOUND COMPOSITIONS HAVING REDUCED FLUORESCENCE
  申请人：EASTMAN CHEMICAL COMPANY

  公开号：EP0713502A1

  公开（公告）日：1996-05-29
• NAPHTHALENEDICARBOXYLATE CONTAINING POLYESTER BLEND COMPOSITIONS HAVING REDUCED FLUORESCENCE
  申请人：EASTMAN CHEMICAL COMPANY

  公开号：EP0868488A1

  公开（公告）日：1998-10-07
• US5391701A
  申请人：——

  公开号：US5391701A

  公开（公告）日：1995-02-21
• US5418318A
  申请人：——

  公开号：US5418318A

  公开（公告）日：1995-05-23
• US5705600A
  申请人：——

  公开号：US5705600A

  公开（公告）日：1998-01-06