7,8,9,10-tetrahydrobenzo[g]cyclopenta[b]indole | 7234-76-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 7,8,9,10-tetrahydrobenzo[g]cyclopenta[b]indole
• 英文别名: 7,8,9,10-tetrahydro-benzo[g]cyclopent[b]indole；7,8,9,10-Tetrahydro-benzo[g]cyclopent[b]indol；16-Azatetracyclo[8.6.0.02,7.011,15]hexadeca-1(10),2,4,6,8,11(15)-hexaene
• CAS: 7234-76-6
• 化学式: C₁₅H₁₃N
• 分子量: 207.275
• InChiKey: JNRLMIGQGWRTBG-UHFFFAOYSA-N

物化性质

• 沸点：
  406.6±14.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  7,8,9,10-tetrahydrobenzo[g]cyclopenta[b]indole 在 sodium tetrahydroborate 、 三叔丁基膦 、 potassium tert-butylate 、 ammonium acetate 、 palladium diacetate 、 溶剂黄146 、 三氯氧磷 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 44.0h， 生成
  参考文献：
  名称：

  Comparison of performance between benzoindoline and indoline dyes in zinc oxide dye-sensitized solar cell

  摘要：

  The cell performance of novel benzoindoline dyes on zinc oxide prepared by template cathode electro-deposition method was compared with that of known indoline dyes. Among cyanoacrylic, single and double rhodanine acetic acid derivatives, the cyanoacrylic benzoindoline dye showed better performance than the indoline dye (D131) due to larger J(sc) value which comes from its positive E., level and bathochromic UV-vis absorption band. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2011.02.009
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 硫酸 、 溶剂黄146 作用下， 生成 7,8,9,10-tetrahydrobenzo[g]cyclopenta[b]indole
  参考文献：
  名称：

  十五。硝酸对多环吲哚衍生物的作用。第九部分

  摘要：

  DOI：

  10.1039/jr9310000093

文献信息

• Pd‐Catalyzed Dearomatization of Indole Derivatives <i>via</i> Intermolecular Heck Reactions ^†
  作者：Ping Yang、Ren‐Qi Xu、Chao Zheng、Shu‐Li You

  DOI：10.1002/cjoc.201900509

  日期：2020.3

  Pd‐catalyzed intermolecular dearomative Heck reaction of indoles with aryl iodides is described. The challenges on both reactivity and regioselectivity are addressed by the judicious regulation of the geometric and electronic properties of the substrates. An array of indoline derivatives bearing C2‐quaternary center is obtained in good to excellent yields (up to 93%) with exclusive regioselectivity

  描述了Pd催化的吲哚与芳基碘化物的分子间脱芳香性Heck反应。通过对底物的几何和电子性质的明智调节来应对反应性和区域选择性方面的挑战。在操作简单的条件下，可以获得一系列具有C2-季中心的二氢吲哚衍生物，收率好至极好（高达93％），并且具有唯一的区域选择性。机械建议由详细的DFT计算支持。
• Palladium(0)-Catalyzed Intermolecular Allylic Dearomatization of Indoles by a Formal [4+2] Cycloaddition Reaction
  作者：Run-Duo Gao、Qing-Long Xu、Bo Zhang、Yiting Gu、Li-Xin Dai、Shu-Li You

  DOI：10.1002/chem.201602691

  日期：2016.8.8

  Bridged indoline derivatives were synthesized by an intermolecular Pd‐catalyzed allylic dearomatization reaction of substituted indoles. The reaction between indoles and allyl carbonates bearing a nucleophilic alcohol side‐chain proceeds in a cascade fashion, providing bridged indolines in excellent enantioselectivity.

  桥联的二氢吲哚衍生物是通过分子间钯催化的取代吲哚的烯丙基脱芳香化反应合成的。吲哚和带有亲核醇侧链的碳酸烯丙酯之间的反应以级联方式进行，从而以极好的对映选择性提供桥联的二氢吲哚。
• Ruthenium-Catalyzed Synthesis of Indoles from Anilines and Epoxides
  作者：Miguel Peña-López、Helfried Neumann、Matthias Beller

  DOI：10.1002/chem.201304432

  日期：2014.2.10

  A general synthetic route to indoles from readily available anilines and epoxides by using ruthenium catalysis is described. This straightforward transformation allows a variety of indoles to be obtained in good yields by using [Ru3(CO)12]/1,1′‐bis(diphenylphosphino)ferrocene as the catalytic system. Water and hydrogen are formed as the only stoichiometric by‐products, making this process highly atom

  描述了通过使用钌催化从易得的苯胺和环氧化物制备吲哚的一般合成途径。通过使用[Ru 3（CO）12 ] / 1,1'-双（二苯基膦基）二茂铁作为催化体系，这种简单的转化方法可以高收率获得各种吲哚。水和氢是唯一的化学计量副产物，因此该过程具有很高的原子效率。
• <i>N</i>-Heterocyclization of Naphthylamines with 1,2- and 1,3-Diols Catalyzed by an Iridium Chloride/BINAP System
  作者：Hiroomi Aramoto、Yasushi Obora、Yasutaka Ishii

  DOI：10.1021/jo801966u

  日期：2009.1.16

  Benzoquinoline derivatives were successfully synthesized by iridium-catalyzed N-heterocyclization of naphthylamines with diols. For instance, the reaction of 1-naphthylamine with 1,3-propanediol catalyzed by IrCl3 combined with BINAP as a ligand produced 7,8-benzoquinoline in quantitative yield. The N-heterocyclization reaction was found to be markedly influenced by the ligands employed. Benzoindoles were also synthesized by the same strategy from napthylamines with 1,2-diols. A reaction mechanism for the N-heterocyclization of naphthylamines with 1,3-diols by IrCl3 was proposed.
• Comparison of performance between benzoindoline and indoline dyes in zinc oxide dye-sensitized solar cell
  作者：Masaki Matsui、Masaya Kotani、Yasuhiro Kubota、Kazumasa Funabiki、Jiye Jin、Tsukasa Yoshida、Shinji Higashijima、Hidetoshi Miura

  DOI：10.1016/j.dyepig.2011.02.009

  日期：2011.11

  The cell performance of novel benzoindoline dyes on zinc oxide prepared by template cathode electro-deposition method was compared with that of known indoline dyes. Among cyanoacrylic, single and double rhodanine acetic acid derivatives, the cyanoacrylic benzoindoline dye showed better performance than the indoline dye (D131) due to larger J(sc) value which comes from its positive E., level and bathochromic UV-vis absorption band. (C) 2011 Elsevier Ltd. All rights reserved.