(R)-2,2'-bis(8-hydroxy-3,6-dioxa-1-octyloxy)-1,1'-binaphthyl

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-2,2'-bis(8-hydroxy-3,6-dioxa-1-octyloxy)-1,1'-binaphthyl
• 英文别名: 2-[2-[2-[1-[2-[2-[2-(2-Hydroxyethoxy)ethoxy]ethoxy]naphthalen-1-yl]naphthalen-2-yl]oxyethoxy]ethoxy]ethanol
• 化学式: C₃₂H₃₈O₈
• 分子量: 550.649
• InChiKey: MOAXXAQYEXZLLR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  40
• 可旋转键数：
  19
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  95.8
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (R)-2,2'-bis(8-hydroxy-3,6-dioxa-1-octyloxy)-1,1'-binaphthyl 在 氢氧化钾 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 、 乙二醇 为溶剂， 反应 122.0h， 生成 2,3:4,5-bis(1,2-naphtho)-1,6,9,12,15,18,21-heptaoxacyclotricosa-2,4-diene
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1002/(sici)1521-3765(19990301)5:3<984::aid-chem984>3.0.co;2-t
• 作为产物：
  描述：

  三甘醇单苄醚 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 (R)-2,2'-bis(8-hydroxy-3,6-dioxa-1-octyloxy)-1,1'-binaphthyl
  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

• 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。
• Czech, B.; Czech, A.; Bartsch, R. A., Journal of Heterocyclic Chemistry, 1984, vol. 21, p. 341 - 343
  作者：Czech, B.、Czech, A.、Bartsch, R. A.

  DOI：——

  日期：——
• CZECH, B.;CZECH, A.;BARTSCH, R. A., J. HETEROCYCL. CHEM., 1984, 21, N 2, 341-343
  作者：CZECH, B.、CZECH, A.、BARTSCH, R. A.

  DOI：——

  日期：——
• Binaphthyl metallomacrocycles for complexation of neutral molecules
  作者：Arjen M. Reichwein、Willem Verboom、David N. Reinhoudt

  DOI：10.1002/recl.19931120609

  日期：——

  Binaphthyl salophen crown ethers 1 and 2, containing an immobilized electrophilic uranyl cation, were synthesized by cyclization of dialdehyde 10 with 1,2-benzenediamine (14) or cis-1,2-cyclohexanediamine (15), respectively, in the presence of Ba2+ as a template ion and subsequent transmetallation with UO22+. Solid complexes of urea and 1 and 2 were isolated. Molecular-mechanics calculations show that

  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。
• 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.