(S)-2,2'-dimethoxy-1,1'-binaphthyl-3,3'-diamine

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-2,2'-dimethoxy-1,1'-binaphthyl-3,3'-diamine
• 英文别名: 2,2’-dimethoxy-[1,1’-binaphthalene]-3,3’-diamine；(S)-2,2'-dimethoxy-(1,1'-binaphthalene)-3,3'-diamine；4-(3-Amino-2-methoxynaphthalen-1-yl)-3-methoxynaphthalen-2-amine；4-(3-amino-2-methoxynaphthalen-1-yl)-3-methoxynaphthalen-2-amine
• 化学式: C₂₂H₂₀N₂O₂
• 分子量: 344.413
• InChiKey: DXEYLSBCOGNYOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  70.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-2,2'-dimethoxy-1,1'-binaphthyl-3,3'-diamine 在 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 N³,N³'-bis-(2,2'-dimethoxy-3'-(2,2,2-trifluoroacetamido)-1,1'-binaphthyl-3-yl)-2,2'-dimethoxy-1,1'-binaphthyl-3,3'-dicarboxamide
  参考文献：
  名称：

  BINOL-Based FoldamersAccess to Oligomers with Diverse Structural Architectures

  摘要：

  In this article, we report on the synthesis and conformation of a new family of aromatic oligoamide foldamers based on binaphthol (BINOL) monomers. A series of oligomers with differing chirality of the individual BINOL building blocks and mixed sequences of alternate BINOL and pyridyl building blocks has been synthesized and structurally characterized. NMR and quantum chemical calculations on the basis of ab initio MO theory were performed to obtain insight into the conformational features of these oligomers. It is shown that the combination of these inherently chiral aromatic building blocks provides a novel access to a wide variety of conformationally ordered synthetic oligomers with diverse and dazzling structural architectures distinct from those classically observed.

  DOI：

  10.1021/jo070396y
• 作为产物：
  描述：

  2-羟基-3-萘甲酸 在 氢氧化钾 、 sodium azide 、 草酰氯 、 硫酸 、 potassium carbonate 、 N,N-二甲基甲酰胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 丙酮 、 苯 为溶剂， 反应 86.25h， 生成 (S)-2,2'-dimethoxy-1,1'-binaphthyl-3,3'-diamine
  参考文献：
  名称：

  BINOL-Based FoldamersAccess to Oligomers with Diverse Structural Architectures

  摘要：

  In this article, we report on the synthesis and conformation of a new family of aromatic oligoamide foldamers based on binaphthol (BINOL) monomers. A series of oligomers with differing chirality of the individual BINOL building blocks and mixed sequences of alternate BINOL and pyridyl building blocks has been synthesized and structurally characterized. NMR and quantum chemical calculations on the basis of ab initio MO theory were performed to obtain insight into the conformational features of these oligomers. It is shown that the combination of these inherently chiral aromatic building blocks provides a novel access to a wide variety of conformationally ordered synthetic oligomers with diverse and dazzling structural architectures distinct from those classically observed.

  DOI：

  10.1021/jo070396y

文献信息

• Stereochemical studies—VIII
  作者：H. Akimoto、S. Yamada

  DOI：10.1016/s0040-4020(01)91765-x

  日期：1971.1

  reaction sequences shown in Figs 1-5, the absolute configuration of optically active biaryl derivatives such as biphenyl, binaphthyl, bianthryl and bianthroaquinonyl have been clearly established, based on the standard compound (R)-(+)-I, in the binaphthyl system, whose absolute configuration was unequivocally determined by the anomalous X-ray diffraction method.

  根据图1-5中所示的反应顺序，基于标准化合物（R）-（+）-I，已经清楚地确定了光学活性联芳基衍生物如联苯，联萘基，联蒽基和联蒽醌基的绝对构型。双萘基系统，其绝对构型是通过异常X射线衍射法明确确定的。
• A New Chiral Binaphthalene-Based Fluorescence Polymer Sensor for the Highly Enantioselective Recognition of Phenylalaninol
  作者：Guo Wei、Shuwei Zhang、Chunhui Dai、Yiwu Quan、Yixiang Cheng、Chengjian Zhu

  DOI：10.1002/chem.201302726

  日期：2013.11.18

  excellent enantioselective recognition behavior with enantiomeric fluorescence difference ratios (ef) as high as 8.99. More importantly, chiral polymer P‐1 displays a bright blue fluorescence color change upon the addition of (D)‐phenylalaninol under a commercially available UV lamp, which can be clearly observed by the naked eye. On the contrary, chiral polymer P‐2 showed weaker enantioselective fluorescence

  一个新的（小号）基于联萘系聚合物（P - 1）通过的5,5'的聚合合成- （（2,5-二丁氧基-1,4-亚苯基）双（乙炔-2,1-二基） ）双（2-羟基-3-（哌啶-1-基甲基）苯甲醛（M - 1）与（S）-2,2'-二甲氧基-（1,1'-联萘）-3,3'-二胺（中号- 2）通过形成席夫碱的;相应的手性聚合物（P - 2）可以通过聚合物的还原而得到P - 1用NaBH 4手性聚合物。P - 1对（D）-苯丙氨醇表现出显着的“开启”荧光增强响应，对映体荧光差比（ef）高达8.99 ，具有出色的对映选择性识别行为。更重要的是，在市售紫外线灯下添加（D）-苯丙氨醇后，手性聚合物P - 1会显示出明亮的蓝色荧光色变化，这可以通过肉眼清楚地观察到。相反，手性聚合物P - 2对苯丙氨醇的对映异构体显示较弱的对映选择性荧光能力。
• (S)-Binaphthalene-based fluorescence polymer sensors for direct and visual F− detection
  作者：Fei Li、Guo Wei、Yuan Sheng、Yiwu Quan、Yixiang Cheng、Chengjian Zhu

  DOI：10.1016/j.polymer.2014.09.017

  日期：2014.10

  (S)-binaphthalene-based polymer sensors P-1 and P-2 could be synthesized by the polymerization of 5,5'-((2,5-dibutoxy-1,4-phenylene)bis(ethyne-2,1-diyl))bis-(2-hydroxy-3-(piperidin-1-ylmethyl) benzaldehyde (M-1) with (S)-2,2'-dimethoxy-(1,1'-binaphthalene)-6,6'-diamine (M-2) and (S)-2,2'-dimethoxy-(1,1'-binaphthalene)-3,3'-diamine (M-3) via nucleophilic addition-elimination reaction. The fluorescence emission of P-1 and P-2 could exhibit gradual enhancement behavior upon the addition of F- Compared with other anions, such as Cl-, Br-, l(-), HSO4-, ClO4-, H2PO4-, ACO(-), and NO3- F- could lead to the most remarkable fluorescence enhancement as high as 3.67-fold for P-1 and 12.85-fold for P-2, respectively. More importantly, both two polymer sensors P-1 and P-2 can display a bright yellow fluorescence color change for F- under a commercially available UV lamp, which could be clearly observed by the naked eyes for direct visual detection of F-. (C) 2014 Elsevier Ltd. All rights reserved.