8,8'-bis(3-butylureido)-2,2'-binaphthalene | 1273557-37-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 8,8'-bis(3-butylureido)-2,2'-binaphthalene
• 英文别名: 1-Butyl-3-[7-[8-(butylcarbamoylamino)naphthalen-2-yl]naphthalen-1-yl]urea；1-butyl-3-[7-[8-(butylcarbamoylamino)naphthalen-2-yl]naphthalen-1-yl]urea
• CAS: 1273557-37-1
• 化学式: C₃₀H₃₄N₄O₂
• 分子量: 482.626
• InChiKey: QPPITODNOJVMOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  82.3
• 氢给体数：
  4
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  8,8'-bis(3-butylureido)-2,2'-binaphthalene 、 四丁基醋酸铵 以 二甲基亚砜 、 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Anion recognition by 2,2′-binaphthalene derivatives bearing urea and thiourea groups at 8- and 8′-positions by UV–vis and fluorescence spectroscopies

  摘要：

  Synthesis and anion recognition properties of 2,2'-binaphthalene derivatives bearing two thiourea (1) and urea (2) groups at 8- and 8'-positions were studied. The structure of receptor 1 was determined by Xray crystallography. UV-vis spectra of the receptors showed characteristic changes around 300-400 nm through isosbestic points upon the addition of biologically relevant anions such as acetate, dihydrogenphosphate, and chloride in MeCN and DMSO due to restriction of the rotation around the single bond connecting two naphthyl moieties by cooperative guest binding of two recognition sites. Job's plots showed 1:1 complexation for guest anions. The fluorescence quantum yields of free form of 1 and 2 in MeCN were determined to be 0.021 and 0.57, respectively. The fluorescence intensities of the receptors diminished upon the addition of anions in MeCN. The association constants of receptors 1 and 2 were one or two orders of magnitude greater than the corresponding monothiourea and urea receptors 3 and 4 indicating cooperative hydrogen bonding with guest anions. The selectivity trends of association of anions were F->AcO->H2PO4->Cl->>HSO4- approximate to NO3- approximate to Br- approximate to l(-) for 1, and F->AcO- approximate to Cl->H2PO4-> Br->HSO4->l(-) approximate to NO3- for 2. Receptor 2 showed remarkable Cl- selectivity presumably owing to suitable orientation for effective hydrogen bond formation with Cl-. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.12.004
• 作为产物：
  描述：

  7-溴萘-1-胺 在 2,2'-联吡啶 、 三苯基膦 、 nickel dichloride 、 锌 作用下， 以 乙醇 、 N,N-二甲基乙酰胺 为溶剂， 反应 63.0h， 生成 8,8'-bis(3-butylureido)-2,2'-binaphthalene
  参考文献：
  名称：

  Anion recognition by 2,2′-binaphthalene derivatives bearing urea and thiourea groups at 8- and 8′-positions by UV–vis and fluorescence spectroscopies

  摘要：

  Synthesis and anion recognition properties of 2,2'-binaphthalene derivatives bearing two thiourea (1) and urea (2) groups at 8- and 8'-positions were studied. The structure of receptor 1 was determined by Xray crystallography. UV-vis spectra of the receptors showed characteristic changes around 300-400 nm through isosbestic points upon the addition of biologically relevant anions such as acetate, dihydrogenphosphate, and chloride in MeCN and DMSO due to restriction of the rotation around the single bond connecting two naphthyl moieties by cooperative guest binding of two recognition sites. Job's plots showed 1:1 complexation for guest anions. The fluorescence quantum yields of free form of 1 and 2 in MeCN were determined to be 0.021 and 0.57, respectively. The fluorescence intensities of the receptors diminished upon the addition of anions in MeCN. The association constants of receptors 1 and 2 were one or two orders of magnitude greater than the corresponding monothiourea and urea receptors 3 and 4 indicating cooperative hydrogen bonding with guest anions. The selectivity trends of association of anions were F->AcO->H2PO4->Cl->>HSO4- approximate to NO3- approximate to Br- approximate to l(-) for 1, and F->AcO- approximate to Cl->H2PO4-> Br->HSO4->l(-) approximate to NO3- for 2. Receptor 2 showed remarkable Cl- selectivity presumably owing to suitable orientation for effective hydrogen bond formation with Cl-. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.12.004

文献信息

• Anion recognition by 2,2′-binaphthalene derivatives bearing urea and thiourea groups at 8- and 8′-positions by UV–vis and fluorescence spectroscopies
  作者：Shin-ichi Kondo、Masanori Nagamine、Satoshi Karasawa、Masaya Ishihara、Masafumi Unno、Yumihiko Yano

  DOI：10.1016/j.tet.2010.12.004

  日期：2011.2

  Synthesis and anion recognition properties of 2,2'-binaphthalene derivatives bearing two thiourea (1) and urea (2) groups at 8- and 8'-positions were studied. The structure of receptor 1 was determined by Xray crystallography. UV-vis spectra of the receptors showed characteristic changes around 300-400 nm through isosbestic points upon the addition of biologically relevant anions such as acetate, dihydrogenphosphate, and chloride in MeCN and DMSO due to restriction of the rotation around the single bond connecting two naphthyl moieties by cooperative guest binding of two recognition sites. Job's plots showed 1:1 complexation for guest anions. The fluorescence quantum yields of free form of 1 and 2 in MeCN were determined to be 0.021 and 0.57, respectively. The fluorescence intensities of the receptors diminished upon the addition of anions in MeCN. The association constants of receptors 1 and 2 were one or two orders of magnitude greater than the corresponding monothiourea and urea receptors 3 and 4 indicating cooperative hydrogen bonding with guest anions. The selectivity trends of association of anions were F->AcO->H2PO4->Cl->>HSO4- approximate to NO3- approximate to Br- approximate to l(-) for 1, and F->AcO- approximate to Cl->H2PO4-> Br->HSO4->l(-) approximate to NO3- for 2. Receptor 2 showed remarkable Cl- selectivity presumably owing to suitable orientation for effective hydrogen bond formation with Cl-. (C) 2010 Elsevier Ltd. All rights reserved.