6,6'-dibromo-2,2'-(3-oxa-pentane-1,5-diyldioxy)-bis-pyridine | 56446-69-6

• 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'-(3-oxa-pentane-1,5-diyldioxy)-bis-pyridine
• 英文别名: 2-Bromo-6-[2-[2-(6-bromopyridin-2-yl)oxyethoxy]ethoxy]pyridine
• CAS: 56446-69-6
• 化学式: C₁₄H₁₄Br₂N₂O₃
• 分子量: 418.085
• InChiKey: DEYIHADHRQYKMY-UHFFFAOYSA-N

物化性质

• 熔点：
  84-85 °C(Solv: toluene (108-88-3); ethyl acetate (141-78-6))
• 沸点：
  479.9±45.0 °C(Predicted)
• 密度：
  1.629±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  53.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6,6'-dibromo-2,2'-(3-oxa-pentane-1,5-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 11,14,17-Trioxa-22,23-diazatetracyclo[16.3.1.16,10.02,5]tricosa-1(22),6(23),7,9,18,20-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 、 二乙二醇 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97%的产率得到6,6'-dibromo-2,2'-(3-oxa-pentane-1,5-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：——
• NEWKOME G. R.; NAYAK A.; MCCLURE G. L.; DANESH-KHOSHBOO F.; BROUSSARD-SIM+, J. ORG. CHEM. <JOCE-AH>, 1977, 42, NO 9, 1500-1508
  作者：NEWKOME G. R.、 NAYAK A.、 MCCLURE G. L.、 DANESH-KHOSHBOO F.、 BROUSSARD-SIM+

  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.