7-phenyl-1-oxa-4,10-dithia-7-azacyclododecane | 223264-16-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 7-phenyl-1-oxa-4,10-dithia-7-azacyclododecane
• CAS: 223264-16-2
• 化学式: C₁₄H₂₁NOS₂
• 分子量: 283.459
• InChiKey: FPOLCXZIEOWGTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  63.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-phenyl-1-oxa-4,10-dithia-7-azacyclododecane 在 三氟乙酸 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 生成 1,3,5,7-tetramethyl-8-[4-(1-oxa-4,10-dithia-7-azacyclododec-7-yl)phenyl]-4H-3a,4a-diaza-4-difluorobora-s-indacene
  参考文献：
  名称：

  On the Development of Sensor Molecules that Display Fe^III-amplified Fluorescence

  摘要：

  Incorporation of a tailor-made size-restricted dithia-aza-oxa macrocycle, 1-oxa-4,10-dithia-7aza-cyclocloclecane, via a phenyl linker into two fluorescent sensor molecules with electronically decoupled, rigidly fixed, and sterically preoriented architectures, a 1,3,5-triaryl-Delta(2)-pyrazoline and a meso-substituted boron-dipyrromethene (BDP), yields amplified fluorescence in the red-visible spectral range upon binding of Fe-III ions. The response to Fe-III and potentially interfering metal ions is studied in highly polar aprotic and protic solvents for both probes as well as in neat and buffered aqueous solution for one of the sensor molecules, the BDP derivative. In organic solvents, the fluorescence of both indicators is quenched by an intramolecular charge or electron transfer in the excited state and coordination of Fe-III leads to a revival of their fluorescence without pronounced spectral shifts. Most remarkably, the unbound BDP derivative shows dual emission in water and can be employed for the selective ratiometric signaling of Fe-III in buffered aqueous solutions.

  DOI：

  10.1021/ja050652t
• 作为产物：
  描述：

  N,N-双(2-溴乙基)苯胺 、 2-巯基乙醚 在 sodium isopropylate 作用下， 以 异丙醇 为溶剂， 生成 7-phenyl-1-oxa-4,10-dithia-7-azacyclododecane
  参考文献：
  名称：

  On the Development of Sensor Molecules that Display Fe^III-amplified Fluorescence

  摘要：

  Incorporation of a tailor-made size-restricted dithia-aza-oxa macrocycle, 1-oxa-4,10-dithia-7aza-cyclocloclecane, via a phenyl linker into two fluorescent sensor molecules with electronically decoupled, rigidly fixed, and sterically preoriented architectures, a 1,3,5-triaryl-Delta(2)-pyrazoline and a meso-substituted boron-dipyrromethene (BDP), yields amplified fluorescence in the red-visible spectral range upon binding of Fe-III ions. The response to Fe-III and potentially interfering metal ions is studied in highly polar aprotic and protic solvents for both probes as well as in neat and buffered aqueous solution for one of the sensor molecules, the BDP derivative. In organic solvents, the fluorescence of both indicators is quenched by an intramolecular charge or electron transfer in the excited state and coordination of Fe-III leads to a revival of their fluorescence without pronounced spectral shifts. Most remarkably, the unbound BDP derivative shows dual emission in water and can be employed for the selective ratiometric signaling of Fe-III in buffered aqueous solutions.

  DOI：

  10.1021/ja050652t

文献信息

• Probing Nitrobenzhydrol Uncaging Mechanisms Using FerriCast
  作者：Daniel P. Kennedy、Daniel C. Brown、Shawn C. Burdette

  DOI：10.1021/ol101726a

  日期：2010.10.15

  The FerriCast derivative FC-NDBF was synthesized from 3-methyl-2-nitrodibenzofuran (NDBF). The photochemistry of the target Fe3+ photocage and several related congeners provides mechanistic insight into the uncaging quantum yields of nitrobenzhydrol-derived ligands
• On the Development of Sensor Molecules that Display Fe^III-amplified Fluorescence
  作者：Julia L. Bricks、Anton Kovalchuk、Christian Trieflinger、Marianne Nofz、Michael Büschel、Alexei I. Tolmachev、Jörg Daub、Knut Rurack

  DOI：10.1021/ja050652t

  日期：2005.10.1

  Incorporation of a tailor-made size-restricted dithia-aza-oxa macrocycle, 1-oxa-4,10-dithia-7aza-cyclocloclecane, via a phenyl linker into two fluorescent sensor molecules with electronically decoupled, rigidly fixed, and sterically preoriented architectures, a 1,3,5-triaryl-Delta(2)-pyrazoline and a meso-substituted boron-dipyrromethene (BDP), yields amplified fluorescence in the red-visible spectral range upon binding of Fe-III ions. The response to Fe-III and potentially interfering metal ions is studied in highly polar aprotic and protic solvents for both probes as well as in neat and buffered aqueous solution for one of the sensor molecules, the BDP derivative. In organic solvents, the fluorescence of both indicators is quenched by an intramolecular charge or electron transfer in the excited state and coordination of Fe-III leads to a revival of their fluorescence without pronounced spectral shifts. Most remarkably, the unbound BDP derivative shows dual emission in water and can be employed for the selective ratiometric signaling of Fe-III in buffered aqueous solutions.