4,9-bis(1-methylethoxy)-1,3-diiminobenzo[f]isoindoline | 1195989-42-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4,9-bis(1-methylethoxy)-1,3-diiminobenzo[f]isoindoline
• 英文别名: 3-Imino-4,9-di(propan-2-yloxy)benzo[f]isoindol-1-amine
• CAS: 1195989-42-4
• 化学式: C₁₈H₂₁N₃O₂
• 分子量: 311.384
• InChiKey: GPILFGGCFMMTGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  80.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  、 4,9-bis(1-methylethoxy)-1,3-diiminobenzo[f]isoindoline 在 丙醇 、 碘 、 magnesium 、 三氟乙酸 、 碳酸氢钠 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 9.0h， 以35%的产率得到(6R,7R,15R,16R,24R,25R)-6,7,15,16,24,25-hexamethoxy-6,7,15,16,24,25-hexamethyl-32,39-di(propan-2-yloxy)-5,8,14,17,23,26-hexaoxa-2,11,20,29,41,42,43,44-octazadecacyclo[28.10.1.13,10.112,19.121,28.04,9.013,18.022,27.031,40.033,38]tetratetraconta-1,3(44),4(9),10,12,18,20,22(27),28(42),29,31,33,35,37,39-pentadecaene
  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-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

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.