6,6'-dibromo-2,2'-ethane-1,2-diyldioxy-bis-pyridine | 56446-70-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6,6'-dibromo-2,2'-ethane-1,2-diyldioxy-bis-pyridine
• 英文别名: 6,6'-Dibrom-2,2'-(ethylendioxy)-dipyridin；Pyridine, 2,2'-[1,2-ethanediylbis(oxy)]bis[6-bromo-；2-bromo-6-[2-(6-bromopyridin-2-yl)oxyethoxy]pyridine
• CAS: 56446-70-9
• 化学式: C₁₂H₁₀Br₂N₂O₂
• 分子量: 374.032
• InChiKey: ISNQISAQFDRVJF-UHFFFAOYSA-N

物化性质

• 熔点：
  113-114 °C(Solv: toluene (108-88-3); ethyl acetate (141-78-6))
• 沸点：
  436.6±45.0 °C(Predicted)
• 密度：
  1.722±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  44.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6,6'-dibromo-2,2'-ethane-1,2-diyldioxy-bis-pyridine 在 四(三苯基膦)钯 2,6-二叔丁基-4-甲基苯酚 作用下， 以 甲苯 为溶剂， 反应 32.0h， 生成 11,14-Dioxa-19,20-diazatetracyclo[13.3.1.16,10.02,5]icosa-1(19),6(20),7,9,15,17-hexaene
  参考文献：
  名称：

  Synthesis and Complexing Properties of [2.n](2,6)Pyridinocrownophanes

  摘要：

  [2.n](2,6)Pyridinocrownophanes (3a-e) were efficiently prepared by intramolecular [2 + 2] photocycloaddition of vinylpyridine derivatives under irradiation using a 400-W high-pressure mercury lamp through a Pyrex filter. They were of cis-configuration with respect to the cyclobutane ring, which was proven by the specific methine proton NMR resonances at delta 3.98-4.08. From ESI-MS analysis 3a-e were found to form 1:1 complexes with Ag+ cation. In a liquid-liquid extraction, 3 showed the highest affinity toward Ag+ cation among several heavy metal nitrates. In this series, 3c possessing four ethereal oxygen atoms was found to show the highest Ag+ affinity, according to the liquid-liquid extraction and determination of stability constant with the cation. The photoreactivity of precursor vinylpyridines is discussed by the predictor gamma(r(c)) proposed by Caldwell.

  DOI：

  10.1021/jo0402374
• 作为产物：
  描述：

  2,6-二溴吡啶 、 乙二醇 在 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 以91%的产率得到6,6'-dibromo-2,2'-ethane-1,2-diyldioxy-bis-pyridine
  参考文献：
  名称：

  Synthesis and Complexing Properties of [2.n](2,6)Pyridinocrownophanes

  摘要：

  [2.n](2,6)Pyridinocrownophanes (3a-e) were efficiently prepared by intramolecular [2 + 2] photocycloaddition of vinylpyridine derivatives under irradiation using a 400-W high-pressure mercury lamp through a Pyrex filter. They were of cis-configuration with respect to the cyclobutane ring, which was proven by the specific methine proton NMR resonances at delta 3.98-4.08. From ESI-MS analysis 3a-e were found to form 1:1 complexes with Ag+ cation. In a liquid-liquid extraction, 3 showed the highest affinity toward Ag+ cation among several heavy metal nitrates. In this series, 3c possessing four ethereal oxygen atoms was found to show the highest Ag+ affinity, according to the liquid-liquid extraction and determination of stability constant with the cation. The photoreactivity of precursor vinylpyridines is discussed by the predictor gamma(r(c)) proposed by Caldwell.

  DOI：

  10.1021/jo0402374

文献信息

• NEWKOME G. R.; MCCLURE G. L.; SIMPSON J. B.; DANESH-KHOSHBOO F., J. AMER. CHEM. SOC. <JACS-AT>, 1975, 97, NO 11, 3232-3234
  作者：NEWKOME G. R.、 MCCLURE G. L.、 SIMPSON J. B.、 DANESH-KHOSHBOO F.

  DOI：——

  日期：——
• Synthesis and Complexing Properties of [2.<i>n</i>](2,6)Pyridinocrownophanes
  作者：Seiichi Inokuma、Hayato Ide、Tomomi Yonekura、Takashi Funaki、Shin-ichi Kondo、Satoru Shiobara、Toshitada Yoshihara、Seiji Tobita、Jun Nishimura

  DOI：10.1021/jo0402374

  日期：2005.3.1

  [2.n](2,6)Pyridinocrownophanes (3a-e) were efficiently prepared by intramolecular [2 + 2] photocycloaddition of vinylpyridine derivatives under irradiation using a 400-W high-pressure mercury lamp through a Pyrex filter. They were of cis-configuration with respect to the cyclobutane ring, which was proven by the specific methine proton NMR resonances at delta 3.98-4.08. From ESI-MS analysis 3a-e were found to form 1:1 complexes with Ag+ cation. In a liquid-liquid extraction, 3 showed the highest affinity toward Ag+ cation among several heavy metal nitrates. In this series, 3c possessing four ethereal oxygen atoms was found to show the highest Ag+ affinity, according to the liquid-liquid extraction and determination of stability constant with the cation. The photoreactivity of precursor vinylpyridines is discussed by the predictor gamma(r(c)) proposed by Caldwell.