2,2'-<<1,1'-binaphthalene>-2,2'-diylbis(oxy-2,1-ethanediyloxy-2,1-ethanediyloxy)>bisethanol bis(4-methylbenzenesulfonate) | 682770-85-0

• 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: 2,2'-<<1,1'-binaphthalene>-2,2'-diylbis(oxy-2,1-ethanediyloxy-2,1-ethanediyloxy)>bisethanol bis(4-methylbenzenesulfonate)
• 英文别名: 2,2'-bis(8-tosyloxy-3,6-dioxa-1-octyloxy)-1,1'-binaphthyl；2,2'-[(1,1'-binaphthalene)-2,2'-diylbis(oxy-2,1-ethanediyloxy-2,1-ethanediyloxy)]bisethanol bis(4-methylbenzenesulfonate)；2-[2-[2-[1-[2-[2-[2-[2-(4-methylphenyl)sulfonyloxyethoxy]ethoxy]ethoxy]naphthalen-1-yl]naphthalen-2-yl]oxyethoxy]ethoxy]ethyl 4-methylbenzenesulfonate
• CAS: 682770-85-0；152523-66-5；860780-22-9
• 化学式: C₄₆H₅₀O₁₂S₂
• 分子量: 859.028
• InChiKey: BCFQKLUPWRXSEE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.91
• 重原子数：
  60.0
• 可旋转键数：
  25.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  142.12
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  2,2'-<<1,1'-binaphthalene>-2,2'-diylbis(oxy-2,1-ethanediyloxy-2,1-ethanediyloxy)>bisethanol bis(4-methylbenzenesulfonate) 在 四(三苯基膦)钯 甲酸:三乙胺 1:1 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 水 、 乙腈 为溶剂， 反应 3.0h， 生成 3,3'-<<1,1'-binaphthalene>-2,2'-diylbis(oxy-2,1-ethanediyloxy-2,1-ethanediyloxy-2,1-ethanediyloxy)>bis<2-hydroxybenzaldehyde>
  参考文献：
  名称：

  Binaphthyl metallomacrocycles用于络合中性分子

  摘要：

  通过在Ba的存在下分别用1,2-苯二胺（14）或顺式-1,2-环己二胺（15）对二醛10进行环化反应，合成了含有固定的亲电子性铀酰阳离子的双萘酚盐二酚冠醚1和2。2+作为模板离子，随后与UO 2 2+进行金属转移。分离出尿素与1和2的固体复合物。分子力学计算表明1和2的几何 适用于在金属大环的腔附近引入官能团。

  DOI：

  10.1002/recl.19931120609
• 作为产物：
  描述：

  三乙二醇单苄醚对甲苯磺酸酯 在 palladium on activated charcoal 吡啶 、 氢气 、 potassium carbonate 作用下， 以 乙醇 、 乙酸乙酯 、 乙腈 为溶剂， 反应 3.0h， 生成 2,2'-<<1,1'-binaphthalene>-2,2'-diylbis(oxy-2,1-ethanediyloxy-2,1-ethanediyloxy)>bisethanol bis(4-methylbenzenesulfonate)
  参考文献：
  名称：

  Binaphthyl metallomacrocycles用于络合中性分子

  摘要：

  通过在Ba的存在下分别用1,2-苯二胺（14）或顺式-1,2-环己二胺（15）对二醛10进行环化反应，合成了含有固定的亲电子性铀酰阳离子的双萘酚盐二酚冠醚1和2。2+作为模板离子，随后与UO 2 2+进行金属转移。分离出尿素与1和2的固体复合物。分子力学计算表明1和2的几何 适用于在金属大环的腔附近引入官能团。

  DOI：

  10.1002/recl.19931120609

文献信息

• Photoswitchable Chiral Phase Transfer Catalyst
  作者：Masaru Kondo、Kento Nakamura、Chandu G. Krishnan、Shinobu Takizawa、Tsukasa Abe、Hiroaki Sasai

  DOI：10.1021/acscatal.1c00057

  日期：2021.2.5

  have been developed to control the catalytic activity by photoirradiation. Azobenzene binaphthyl crown ether (ABCE) can switch its reactivity and selectivity through structural transformation of the crown ether moiety induced by E/Z photoisomerization of azobenzene. (Z)-ABCE promoted enantioselective alkylation of the glycine Schiff base to afford chiral amino acid derivatives in good yields with high

  已经开发了基于偶氮-冠醚的光开关手性相转移催化剂，以通过光辐射来控制催化活性。偶氮苯联萘冠醚（ABCE）可以通过偶氮苯的E / Z光异构化诱导的冠醚部分的结构转化来切换其反应性和选择性。（Z）-ABCE促进甘氨酸席夫碱的对映选择性烷基化，以高收率和高对映体比率提供手性氨基酸衍生物。相反，（E）-ABCE阻碍了相同条件下的反应进程。
• Efficient Synthesis of a Chiral [4]Pseudocatenane and Its Derivatives: A Novel Ship's Wheel-like Interlocked Structure
  作者：Xiao-Zhang Zhu、Chuan-Feng Chen

  DOI：10.1002/chem.200600195

  日期：2006.7.17

  A novel chiral[4]pseudocatenane 5H(3)[PF(6)](3) was synthesized efficiently by treatment of a solution of chiral triptycene-based tri(crown ether) 1 and three equivalents of a bis[p-(but-3-enyloxy)benzyl]ammonium salt in CH(2)Cl(2) with a Grubbs II catalyst, followed by hydrogenation. It was found that the ammonium groups in 5H(3)[PF(6)](3) could be deprotonated by 1,8-diazabicyclo[5.4.0]undec-7-ene

  通过处理基于手性三茂基的三（冠醚）1和三当量的bis [p-（但用Grubbs II催化剂在CH（2）Cl（2）中的[-3-烯氧基）苄基]铵盐，然后氢化。发现5H（3）[PF（6）]（3）中的铵基可被乙腈或二甲基亚砜（DMSO）中的1,8-二氮杂双环[5.4.0]十一碳-7-烯（DBU）去质子化）。因此，在DBU的存在下，铵基团的N-酰化反应很容易进行，从而以高收率产生了新一类的中性高度有序的互锁分子。尤其是，加入止挡单元（例如氨基磷酸二乙酯）会导致互锁的分子10分离，形成有趣的船轮状结构，在详细的NMR实验的帮助下进行了结构研究。与1相比，进一步发现在5H（3）[PF（6）]（3）及其衍生物中，（R）-1,1'-联萘生色团在241 nm处的棉花效应大大降低。此外，在互锁的分子中出现了在248 nm处的新的棉花效应。该观察结果可归因于从双萘基单元到位于1腔中的大环的手性转移。
• A [2]Catenane Containing 1,1′-Binaphthyl Units and 1,10-Phenanthroline Fragments: Synthesis and Intermolecular Energy Transfer Processes
  作者：Masatoshi Koizumi、Christiane Dietrich-Buchecker、Jean-Pierre Sauvage

  DOI：10.1002/ejoc.200300572

  日期：2004.2

  chiral copper(I)-complexed [2]catenane consisting of two interlocking 38-membered rings, each ring incorporating a 2,9-diphenyl-1,10-phenanthroline (dpp) and an (S)-1,1′-binaphthyl group, has been prepared by means of a transition metal template strategy. Demetalation afforded the corresponding free chiral [2]catenane. The coordination polyhedron of the Cu(dpp)2 core in this chiral copper(I)-complexed

  一种手性铜 (I) 复合 [2] 链烯，由两个互锁的 38 元环组成，每个环包含一个 2,9-二苯基-1,10-菲咯啉 (dpp) 和一个 (S)-1,1'-联萘基团，已通过过渡金属模板策略制备。脱金属得到相应的游离手性 [2] 链。这种手性铜 (I) 络合 [2] 链烯中 Cu(dpp)2 核的配位多面体反映了手性 1,1'-联萘单元的畸变，如圆二色性 (CD) 测量所证明的那样。发射测量表明，在双发色团化合物 (S)-6 和 (S,S)-9 中，1,1'-联萘组分和 dpp 单元之间的有效能量转移发生在室温下的溶液中。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
• A Dynamically Responsive Chemosensor That Can be Modulated by an Effector: Amplification Sensing by Positive Heterotropic Allosterism
  作者：Sho Suzuki、Amane Homma、Reiya Nishi、Hiroaki Mizuno、Susumu Kawauchi、Gaku Fukuhara

  DOI：10.1246/bcsj.20220088

  日期：2022.8.15

  Induced-fit chemosensors that can control their molecular recognition behavior using external stimuli such as temperature, light, pH, and chemical additives, have attracted much attention from several chemists. In this study, we report a bisporphyrin–bisthiourea–binaphthyl conjugated chemosensor that can be modulated using a chiral dianion. The optical properties of the chemosensor measured using fluorescence and UV/vis absorption spectroscopies, as well as fluorescence lifetime measurements, indicated that the unique conjugation enabled S2 fluorescence. The binding constants of the chemosensor for amino acids were amplified a thousand-fold compared to that of the reference compound due to positive heterotropic allosterism. The present study provides new perspectives for signal amplification of chemosensors by allosterism.

  诱导型化学传感器能够通过温度、光、pH值和化学添加剂等外部刺激来控制其分子识别行为，因此引起了多位化学家的关注。在这项研究中，我们报告了一种双卟啉-双硫脲-联萘共轭化学传感器，该传感器可以使用手性二阴离子进行调节。使用荧光和紫外/可见光吸收光谱以及荧光寿命测量法测得的化学传感器的光学特性表明，独特的共轭结构能够产生S2荧光。由于正异构变构作用，化学传感器对氨基酸的结合常数比参考化
• A Molecular-Level Plug/Socket System: Electronic Energy Transfer from a Binaphthyl Unit Incorporated into a Crown Ether to an Anthracenyl Unit Linked to an Ammonium Ion
  作者：Eléna Ishow、Alberto Credi、Vincenzo Balzani、Francesco Spadola、Luigi Mandolini

  DOI：10.1002/(sici)1521-3765(19990301)5:3<984::aid-chem984>3.0.co;2-t

  日期：1999.3.1

  The reversible acid/base- (hydrogen-bonding-) controlled association between racemic crown ethers incorporating a binaphthyl unit (the socket) and wirelike compounds bearing an anthracenyl unit (the plug) is described. The compounds used were the (+/-)binaphthocrown ethers BN20C6, BN23C7, and BN26C8, the amines 9-methyl(aminomethyl)anthracene (AM) and 9-methyl(aminobenzyl)anthracene (AB), and their hexafluorophosphate salts AMH(+)PF(6)(-) and ABH(+)PF(6)(-). The experiments were carried out in CH,CI, solution. Fluorescence data, (1)H NMR spectra, and molecular modeling all point to the formation of stable, pseudorotaxane-type H-bonded adducts of BN23C7 with AMH(+) and of BN26C8 with AMH+ and ABH(+). These systems can be considered as molecular-level plug/socket devices since they are characterized by i) reversible, acid/base-controlled plug in/plug out behavior and ii) photoinduced flow of electronic energy from the binaphthyl to the anthracenyl unit in the plug in state. The above concepts can be easily extended to systems in which a) the plug in/plug out function is stereoselective and b) light excitation induces an electron flow instead of a flow of electronic energy.