4-(2,3,6,7-Tetrahydro-1H,5H-pyrido[3,2,1-ij]quinolin-9-yl)-3-chlorocyclobut-3-ene-1,2-dione | 159148-48-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 4-(2,3,6,7-Tetrahydro-1H,5H-pyrido[3,2,1-ij]quinolin-9-yl)-3-chlorocyclobut-3-ene-1,2-dione
• 英文别名: 3-(2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinolin-9-yl)-4-chlorocyclobut-3-ene-1,2-dione；3-(1-Azatricyclo[7.3.1.05,13]trideca-5,7,9(13)-trien-7-yl)-4-chlorocyclobut-3-ene-1,2-dione
• CAS: 159148-48-8
• 化学式: C₁₆H₁₄ClNO₂
• 分子量: 287.746
• InChiKey: CXCKXEOPTRLANP-UHFFFAOYSA-N

物化性质

• 沸点：
  503.8±60.0 °C(predicted)
• 密度：
  1.42±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(2,3,6,7-Tetrahydro-1H,5H-pyrido[3,2,1-ij]quinolin-9-yl)-3-chlorocyclobut-3-ene-1,2-dione 在 氢碘酸 、 溶剂黄146 作用下， 以 正丁醇 、 苯 为溶剂， 生成
  参考文献：
  名称：

  Synthesis of Near-Infrared Absorbing Bisquarylium Dyes Bearing Unsymmetrically Extended π-Conjugation Structures

  摘要：

  新型阳离子双菁染料3和4是通过苯并噻唑基菁染料2与一系列4-取代的3-羟基或3-乙氧基环丁-3-烯-1,2-二酮反应制备的。这些染料在近红外区域显示出大且强烈的吸收，吸收峰位置在771至815纳米范围内变化。

  DOI：

  10.1055/s-2002-20034
• 作为产物：
  描述：

  3,4-二氯-3-环丁烯-1,2-二酮 、 久洛尼定 以 苯 为溶剂， 生成 4-(2,3,6,7-Tetrahydro-1H,5H-pyrido[3,2,1-ij]quinolin-9-yl)-3-chlorocyclobut-3-ene-1,2-dione
  参考文献：
  名称：

  Synthesis of Near-Infrared Absorbing Bisquarylium Dyes Bearing Unsymmetrically Extended π-Conjugation Structures

  摘要：

  新型阳离子双菁染料3和4是通过苯并噻唑基菁染料2与一系列4-取代的3-羟基或3-乙氧基环丁-3-烯-1,2-二酮反应制备的。这些染料在近红外区域显示出大且强烈的吸收，吸收峰位置在771至815纳米范围内变化。

  DOI：

  10.1055/s-2002-20034

文献信息

• Synthesis of novel unsymmetrical squarylium dyes absorbing in the near-infrared region †
  作者：Shigeyuki Yagi、Yutaka Hyodo、Shinya Matsumoto、Naoki Takahashi、Hiroshi Kono、Hiroyuki Nakazumi

  DOI：10.1039/a907335c

  日期：——

  Novel unsymmetrical squarylium dyes which absorb in the near-infrared region were synthesized by a stepwise procedure via intermediate 4-substituted 3-hydroxycyclobut-3-ene-1,2-diones. By introducing benz[c,d]indoline or benzo[b]pyran moieties at one end as an electron-donating component, the SQ dyes exhibited their absorption maxima at 739–821 nm with large molar absorption coefficients (log ε = 4.96–5.18) in CHCl3. The X-ray analysis for one of these dyes was also examined to confirm the overall structure of the unsymmetrical SQ dye.

  通过逐步合成方法，通过中间体4-取代的3-羟基环丁-3-烯-1,2-二酮，合成了在近红外区域吸收的新型非对称方酸染料。在一端引入苯并[c,d]吲哚啉或苯并[b]吡喃基团作为电子供体组分，这些方酸染料在氯仿中表现出739至821纳米的吸收峰，摩尔吸收系数较大（log ε = 4.96至5.18）。还对其中一种染料进行了X射线分析，以确认非对称方酸染料的整体结构。
• Synthesis of bisquaraine dyes. Novel homologues of 1,2-squaraines bearing symmetrical and unsymmetrical structures
  作者：Yutaka Hyodo、Hiroyuki Nakazumi、Shigeyuki Yagi、Kazuhisa Nakai

  DOI：10.1039/b104059f

  日期：2001.11.1

  In order to investigate analogous structures of 1,2-squaraine dyes, bisquaraines 1 and 2 are newly prepared as their novel homologues. Symmetrical bisquaraine dye 1, in which the same heterocyclic components are introduced at the 3 and 3′ positions of the bisquaryl skeleton, is obtained by reaction of 4,4′-bi(3-isopropoxycyclobut-3-ene-1,2-dione) 3 with a series of heterocyclic compounds 5. The structure of one of the symmetrical dyes is confirmed by X-ray structural analysis, showing a largely extended π-conjugation system over the whole molecule. The synthesis of unsymmetrical dyes 2, in which different aromatic components are introduced, is established by the reactions of 5 with 3′-monosubstituted bisquarates 6. Each bisquaraine dye exhibits two absorption maxima separated by 56–75 nm, the lower-energy absorption of which is observed at 653–757 nm.

  为了研究1,2-方酸菁染料的类似结构，制备了两种新型同系物——双方酸菁1和2。通过对4,4'-双(3-异丙氧基环丁-3-烯-1,2-二酮)3与一系列杂环化合物5的反应，得到了在双方酸骨架的3和3'位置引入相同杂环组分的对称双方酸菁染料1。通过X射线结构分析证实了其中一种对称染料的结构，显示整个分子中存在一个延伸的π-共轭体系。非对称染料2的合成通过5与3'-单取代双方酸酯6的反应实现，该染料中引入了不同的芳香组分。每种双方酸菁染料均呈现出两个吸收峰，波长间隔为56-75 nm，其中较低能量的吸收峰位于653-757 nm。
• Synthesis of Near-Infrared Absorbing Bisquarylium Dyes Bearing Unsymmetrically Extended π-Conjugation Structures
  作者：Shigeyuki Yagi、Kazuhisa Nakai、Yutaka Hyodo、Hiroyuki Nakazumi

  DOI：10.1055/s-2002-20034

  日期：——

  Novel cationic bisquarylium dyes 3 and 4 were prepared by the reaction of benzothiazolinosquarylium dye 2 with a series of 4-substituted 3-hydroxy or 3-ethoxycyclobut-3-ene-1,2-diones. These dyes exhibit large and intense absorptions in the near-infrared region with varying absorption maxima in the range of 771 to 815 nm.

  新型阳离子双菁染料3和4是通过苯并噻唑基菁染料2与一系列4-取代的3-羟基或3-乙氧基环丁-3-烯-1,2-二酮反应制备的。这些染料在近红外区域显示出大且强烈的吸收，吸收峰位置在771至815纳米范围内变化。