2-(5-bromo-2-nitrophenyl)oxirane | 56759-36-5

• 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-(5-bromo-2-nitrophenyl)oxirane
• 英文别名: 5-Bromo-2-nitro-α,β-epoxystyrol；(5-bromo-2-nitro-phenyl)-oxirane
• CAS: 56759-36-5
• 化学式: C₈H₆BrNO₃
• 分子量: 244.045
• InChiKey: WCEZIPZSZAGHIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  58.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(5-bromo-2-nitrophenyl)oxirane 在 四(三苯基膦)钯 、 sodium azide 、 四溴化碳 、 sodium hydride 、 potassium carbonate 、 三苯基膦 、 sodium iodide 作用下， 以 乙二醇二甲醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 61.5h， 生成 3-[2-{2-(2-azidoethoxy)ethoxy}-1-azidoethyl]-4-nitrostyrene
  参考文献：
  名称：

  Calcium Uncaging with Visible Light

  摘要：

  We have designed a nitroaromatic photochemical protecting group that absorbs visible light in the violet-blue range. The chromophore is a dinitro derivative of bisstyrylthiophene (or BIST) that absorbs light very effectively (epsilon(440) = 66,000 M-1 cm(-1) and two-photon cross section of 350 GM at 775 nm). We developed a "caged calcium" molecule by conjugation of BIST to a Ca2+ chelator that upon laser flash photolysis rapidly releases Ca2+ in <0.2 ms. Using the patch clamp method the optical probe, loaded with Ca2+ was delivered into acutely isolated mouse cardiac myocytes, where either one- and two-photon uncaging of Ca2+ induced highly local or cell-wide physiological Ca2+ signaling events.

  DOI：

  10.1021/jacs.5b11606
• 作为产物：
  描述：

  (carboxymethyl)(4-cyanophenyl)methylsulfonium trifluoromethanesulfonate 、 5-溴-2-硝基苯甲醛 在 caesium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 2.67h， 以74%的产率得到2-(5-bromo-2-nitrophenyl)oxirane
  参考文献：
  名称：

  Calcium Uncaging with Visible Light

  摘要：

  We have designed a nitroaromatic photochemical protecting group that absorbs visible light in the violet-blue range. The chromophore is a dinitro derivative of bisstyrylthiophene (or BIST) that absorbs light very effectively (epsilon(440) = 66,000 M-1 cm(-1) and two-photon cross section of 350 GM at 775 nm). We developed a "caged calcium" molecule by conjugation of BIST to a Ca2+ chelator that upon laser flash photolysis rapidly releases Ca2+ in <0.2 ms. Using the patch clamp method the optical probe, loaded with Ca2+ was delivered into acutely isolated mouse cardiac myocytes, where either one- and two-photon uncaging of Ca2+ induced highly local or cell-wide physiological Ca2+ signaling events.

  DOI：

  10.1021/jacs.5b11606

文献信息

• Pasaribu,S.J.; Williams,L.R., Australian Journal of Chemistry, 1975, vol. 28, p. 1023 - 1030
  作者：Pasaribu,S.J.、Williams,L.R.

  DOI：——

  日期：——
• PASAVIBU S. J.; WILLIAMS L. R., AUSTRAL. J. CHEM. <AJCH-AS>, 1975, 28, NO 5, 1023-1030
  作者：PASAVIBU S. J.、 WILLIAMS L. R.

  DOI：——

  日期：——