1,4-bis(1-methylethoxy)-2,3-naphthalenedicarbonitrile | 1195989-41-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,4-bis(1-methylethoxy)-2,3-naphthalenedicarbonitrile
• 英文别名: 1,4-Di(propan-2-yloxy)naphthalene-2,3-dicarbonitrile
• CAS: 1195989-41-3
• 化学式: C₁₈H₁₈N₂O₂
• 分子量: 294.353
• InChiKey: NBQWDNGWQJQBPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  66
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,4-bis(1-methylethoxy)-2,3-naphthalenedicarbonitrile 在 氨 、 sodium 作用下， 以 乙二醇 为溶剂， 以85%的产率得到4,9-bis(1-methylethoxy)-1,3-diiminobenzo[f]isoindoline
  参考文献：
  名称：

  Synthesis of Heteroatom Substituted Naphthoporphyrazine Derivatives with Near-Infrared Absorption and Emission

  摘要：

  In an effort to develop effective new optical contrast agents, we report the synthesis of porphyrazines (pzs) of the form H-2[pz(A(4-n);C-n)], n = 1, and 2 (trans-), where "A" represents peripheral heteroatom (S- and O-) R-groups and "C" is a fused, beta,beta'-diisopropyloxynaphtho group. The sulfide appended trans-H-2[pz(A(2);C-2)] pz (7) has the longest wavelength absorption, similar to 874 nm (log epsilon = 4.53), and S-1 fluorescence at similar to 927 nm, wavelengths within the window of maximum tissue penetration. Emission from the oxygen-atom appended naphtho-pzs (8, 9) has been observed within carcinoma cells, confirming cellular uptake and their potential use as optical agents.

  DOI：

  10.1021/jo9026947
• 作为产物：
  描述：

  1,4-二羟基-2,3-萘二腈 、 2-溴丙烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以88%的产率得到1,4-bis(1-methylethoxy)-2,3-naphthalenedicarbonitrile
  参考文献：
  名称：

  Synthesis of Heteroatom Substituted Naphthoporphyrazine Derivatives with Near-Infrared Absorption and Emission

  摘要：

  In an effort to develop effective new optical contrast agents, we report the synthesis of porphyrazines (pzs) of the form H-2[pz(A(4-n);C-n)], n = 1, and 2 (trans-), where "A" represents peripheral heteroatom (S- and O-) R-groups and "C" is a fused, beta,beta'-diisopropyloxynaphtho group. The sulfide appended trans-H-2[pz(A(2);C-2)] pz (7) has the longest wavelength absorption, similar to 874 nm (log epsilon = 4.53), and S-1 fluorescence at similar to 927 nm, wavelengths within the window of maximum tissue penetration. Emission from the oxygen-atom appended naphtho-pzs (8, 9) has been observed within carcinoma cells, confirming cellular uptake and their potential use as optical agents.

  DOI：

  10.1021/jo9026947

文献信息

• Synthesis of Heteroatom Substituted Naphthoporphyrazine Derivatives with Near-Infrared Absorption and Emission
  作者：Evan R. Trivedi、Sangwan Lee、Hong Zong、Carl M. Blumenfeld、Anthony G. M. Barrett、Brian M. Hoffman

  DOI：10.1021/jo9026947

  日期：2010.3.5

  In an effort to develop effective new optical contrast agents, we report the synthesis of porphyrazines (pzs) of the form H-2[pz(A(4-n);C-n)], n = 1, and 2 (trans-), where "A" represents peripheral heteroatom (S- and O-) R-groups and "C" is a fused, beta,beta'-diisopropyloxynaphtho group. The sulfide appended trans-H-2[pz(A(2);C-2)] pz (7) has the longest wavelength absorption, similar to 874 nm (log epsilon = 4.53), and S-1 fluorescence at similar to 927 nm, wavelengths within the window of maximum tissue penetration. Emission from the oxygen-atom appended naphtho-pzs (8, 9) has been observed within carcinoma cells, confirming cellular uptake and their potential use as optical agents.