2,2,2-trifluoro-1-(4,5,6,7-tetrahydro-1H-indol-2-yl)ethanol | 1334583-78-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2,2,2-trifluoro-1-(4,5,6,7-tetrahydro-1H-indol-2-yl)ethanol
• 英文别名: Trifluoro-1-(4,5,6,7-tetrahydroindol-2-yl)ethanol
• CAS: 1334583-78-6
• 化学式: C₁₀H₁₂F₃NO
• 分子量: 219.207
• InChiKey: TVWALKJABHWYEH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  36
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,2,2-trifluoro-1-(4,5,6,7-tetrahydro-1H-indol-2-yl)ethanol 在 四磷十氧化物 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 17.0h， 生成
  参考文献：
  名称：

  基于环烷吡咯的不对称内消旋-CF 3 -BODIPY染料

  摘要：

  已经使用包括作为关键步骤的吡咯与三氟（2,3-环烷吡咯-2-基）乙醇缩合的方法合成了新的内消旋CF 3-取代的BODIPY衍生物。如此获得的二吡咯甲烷与DDQ进一步反应，然后与BF 3络合导致苯并[b]稠合（在二吡咯甲烷由三氟（4,5,6,7-四氢吲哚-2-基）乙醇制得的情况下）或环庚烷[b]稠合的饱和或部分饱和的BODIPY染料。后者表现出强烈的红色荧光（λ EM  = 588-634纳米，Φ ˚F = 0.54–0.68），而在极性或非极性溶剂中，苯并[b]融合均不发出荧光。进行的量子化学计算（TD-CAM-B3LYP / SVP）解释了光谱结果。

  DOI：

  10.1016/j.dyepig.2020.108228
• 作为产物：
  描述：

  4,5,6,7-四氢吲哚 在 吡啶 、 甲醇 、 sodium tetrahydroborate 、 碳酸氢钠 作用下， 以 乙醚 为溶剂， 反应 0.75h， 生成 2,2,2-trifluoro-1-(4,5,6,7-tetrahydro-1H-indol-2-yl)ethanol
  参考文献：
  名称：

  Asymmetric meso-CF3-dipyrromethanes with amino- and heterocyclic functions from trifluoro(pyrrolyl)ethanols and pyrroles

  摘要：

  Asymmetric meso-CF3-dipyrromethanes with amino- and nitrogen heterocyclic functions, a new family of the BODIPY dye precursors, have been synthesized in 70-90 % yield by condensation of trifluoro(pyrrolyl)ethanols with pyrroles in the presence of AlCl3. This catalyst, for the first time, was shown to be more efficient than commonly used P2O5, which was entirely inactive in the condensation of pyrroles having basic substituents (amino group and pyrazole moiety).

  DOI：

  10.1016/j.jfluchem.2020.109455

文献信息

• Hydroxyalkylation of 4,5,6,7-tetrahydroindole with polyfluorocarbonyl compounds as a route to 2-substituted indoles
  作者：Andrei L. Sigan、Dmitrii V. Gusev、Nikolai D. Chkanikov、Elena Yu. Shmidt、Andrei V. Ivanov、Al’bina I. Mihaleva

  DOI：10.1016/j.tetlet.2011.07.071

  日期：2011.9

  hydroxyalkylation of 4,5,6,7-tetrahydroindole at position 2 using highly electrophilic polyfluorocarbonyl compounds was performed for the first time. Oxidation of the products thus formed leads to indoles having 2-hydroxypolyfluoroalkyl and polyfluoroacyl groups.

  第一次使用高度亲电的多氟羰基化合物在位置2进行了4,5,6,7-四氢吲哚的区域选择性羟烷基化反应。如此形成的产物的氧化导致具有2-羟基多氟烷基和多氟酰基的吲哚。
• Asymmetric meso-CF3-BODIPY dyes based on cycloalkanopyrroles
  作者：Denis N. Tomilin、Elena F. Sagitova、Konstantin B. Petrushenko、Lyubov N. Sobenina、Igor A. Ushakov、Guoqiang Yang、Rui Hu、Boris A. Trofimov

  DOI：10.1016/j.dyepig.2020.108228

  日期：2020.5

  with BF3 leads to either benzo[b]-fused (in the case of dipyrromethanes obtained from trifluoro(4,5,6,7-tetrahydroindol-2-yl)ethanol) or cycloheptano[b]-fused saturated or partially saturated BODIPY dyes. The latter exhibit strong red fluorescence (λem = 588–634 nm, Φf = 0.54–0.68), while benzo[b]-fused do not fluoresce at all in either polar or non-polar solvents. The performed quantum-chemical calculations

  已经使用包括作为关键步骤的吡咯与三氟（2,3-环烷吡咯-2-基）乙醇缩合的方法合成了新的内消旋CF 3-取代的BODIPY衍生物。如此获得的二吡咯甲烷与DDQ进一步反应，然后与BF 3络合导致苯并[b]稠合（在二吡咯甲烷由三氟（4,5,6,7-四氢吲哚-2-基）乙醇制得的情况下）或环庚烷[b]稠合的饱和或部分饱和的BODIPY染料。后者表现出强烈的红色荧光（λ EM  = 588-634纳米，Φ ˚F = 0.54–0.68），而在极性或非极性溶剂中，苯并[b]融合均不发出荧光。进行的量子化学计算（TD-CAM-B3LYP / SVP）解释了光谱结果。
• Asymmetric meso-CF3-dipyrromethanes with amino- and heterocyclic functions from trifluoro(pyrrolyl)ethanols and pyrroles
  作者：Denis N. Tomilin、Lyubov N. Sobenina、Olga V. Petrova、Elena F. Sagitova、Arsalan B. Budaev、Igor A. Ushakov、Andrey V. Ivanov、Boris A. Trofimov

  DOI：10.1016/j.jfluchem.2020.109455

  日期：2020.3

  Asymmetric meso-CF3-dipyrromethanes with amino- and nitrogen heterocyclic functions, a new family of the BODIPY dye precursors, have been synthesized in 70-90 % yield by condensation of trifluoro(pyrrolyl)ethanols with pyrroles in the presence of AlCl3. This catalyst, for the first time, was shown to be more efficient than commonly used P2O5, which was entirely inactive in the condensation of pyrroles having basic substituents (amino group and pyrazole moiety).