6-bromo-2-methoxy-9H-carbazole

• 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: 6-bromo-2-methoxy-9H-carbazole
• 英文别名: 6-bromo-2-methoxycarbazole；6-Bromo-2-methoxy-9H-carbazole
• 化学式: C₁₃H₁₀BrNO
• 分子量: 276.132
• InChiKey: ZFKAJOPUDZBRPE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  25
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6-bromo-2-methoxy-9H-carbazole 在 2-吡啶甲酸 、 potassium phosphate 、 copper(l) iodide 、 sodium acetate 、 吡啶盐酸盐 、 trans-1,2-cyclohexanediamine 作用下， 以 1,4-二氧六环 、 N-甲基吡咯烷酮 、 二甲基亚砜 、 苯甲腈 、 甲苯 为溶剂， 反应 80.0h， 生成
  参考文献：
  名称：

  ORGANOMETALLIC COMPOUND, ORGANIC LIGHT-EMITTING DEVICE INCLUDING ORGANOMETALLIC COMPOUND, AND DIAGNOSTIC COMPOSITION INCLUDING ORGANOMETALLIC COMPOUND

  摘要：

  一种由公式1表示的有机金属化合物，包括该有机金属化合物的有机发光器件，以及包括该有机金属化合物的诊断组成物：M11（L11）n11（L12）n12公式1其中，在公式1中，M11是第一行过渡金属、第二行过渡金属或第三行过渡金属，L11是由公式1-1表示的配体，L12是单齿配体或双齿配体，n11为1，n12为0、1或2：其中，在公式1-1中，Y11、A11、T11、k11、k12、k13、b11、E11到E13和R11到R17在规范中描述，*1到*4分别独立表示与M11的结合位点。

  公开号：

  US20200354393A1
• 作为产物：
  描述：

  2,4-二溴硝基苯 在 铜 、 亚磷酸三乙酯 作用下， 生成 6-bromo-2-methoxy-9H-carbazole
  参考文献：
  名称：

  Vanadium-Catalyzed Regioselective Oxidative Coupling of 2-Hydroxycarbazoles

  摘要：

  The first regioselective oxidative coupling of 2-hydroxycarbazoles is described. With a vanadium catalyst and oxygen as the terminal oxidant, dimers with an ortho-ortho' coupling pattern were obtained with high selectivity. Further oxidation led to ortho'-ortho' coupling to generate a tetramer, which provided insight that the atropisomerization barriers of the unsymmetrical biaryl bonds are much lower than expected.

  DOI：

  10.1021/ol503521b

文献信息

• An Organic Intermolecular Dehydrogenative Annulation Reaction
  作者：Saikat Maiti、Tapas Kumar Achar、Prasenjit Mal

  DOI：10.1021/acs.orglett.7b00562

  日期：2017.4.21

  The discovery of a direct method for the synthesis of three-ring heterocyclic carbazoles from unactivated arenes and anilides by a metal-free (organic) intermolecular dehydrogenative annulation reaction under ambient laboratory conditions is reported. Iodine(III) was used as the sole reagent either stoichiometrically from inexpensive phenyliodine diacetate or organocatalytically by in situ generation

  报道了在环境实验室条件下通过无金属（有机）分子间脱氢环化反应从未活化的芳烃和苯胺合成三环杂环咔唑的直接方法的发现。碘（III）用作唯一的试剂，从廉价的二乙酸苯基碘二乙酸酯化学计量或从PhI– m CPBA原位生成有机催化。在一个步骤中，两个串联的C–C和C–N键的形成反应就可以从两个不同的芳烃官能化三个C（sp 2）–H键和一个N（sp 3）–H键。
• Fluorescent carbazole-derived α-amino acids: structural mimics of tryptophan
  作者：Rebecca Clarke、Liyao Zeng、Bethany C. Atkinson、Malcolm Kadodwala、Andrew R. Thomson、Andrew Sutherland

  DOI：10.1039/d4sc01173b

  日期：2024.4.24

  Fluorescent tags are commonly used for imaging of proteins and peptides during biological events; however, the large size of dyes can disrupt protein structure and function, and typically require the use of a chemical spacer. Herein, we report the synthesis of a new class of fluorescent unnatural α-amino acid, containing carbazole side-chains designed to mimic L-tryptophan and thus, readily incorporated

  荧光标签通常用于生物事件期间蛋白质和肽的成像；然而，大尺寸的染料会破坏蛋白质的结构和功能，并且通常需要使用化学间隔基。在此，我们报告了一类新型荧光非天然 α-氨基酸的合成，其含有旨在模拟L-色氨酸的咔唑侧链，因此很容易掺入肽中。该氨基酸以根岸交叉偶联反应为关键步骤构建，并表现出强烈的荧光发射，在有机溶剂和水中均具有高量子产率。与固相肽合成相兼容，咔唑氨基酸被用来取代 β-发夹模型肽中的色氨酸，并显示出是保留构象的紧密结构模拟物。它们还被发现是生物事件的有效荧光分子报告基因。掺入 WW 结构域蛋白的富含脯氨酸的配体中表明，咔唑氨基酸的荧光特性可用于测量这一重要生物信号传导过程的蛋白质-蛋白质结合相互作用。
• ORGANOMETALLIC COMPLEX AND LIGHT-EMITTING DEVICE
  申请人：SEMICONDUCTOR ENERGY LABORATORY CO., LTD.

  公开号：US20240174706A1

  公开（公告）日：2024-05-30

  A novel organometallic complex that is highly convenient, useful, or reliable, and a light-emitting device are provided. The organometallic complex is represented by General Formula (G2). In General Formula (G2), each of R 1 to R 6 , R 8 to R 22 , and R 31 to R 34 independently represents hydrogen (including deuterium), an alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, at least one of R 31 to R 34 represents an alkyl group having 1 to 10 carbon atoms or a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, and n is an integer of 1 to 4.
• Vanadium-Catalyzed Regioselective Oxidative Coupling of 2-Hydroxycarbazoles
  作者：Lei Liu、Patrick J. Carroll、Marisa C. Kozlowski

  DOI：10.1021/ol503521b

  日期：2015.2.6

  The first regioselective oxidative coupling of 2-hydroxycarbazoles is described. With a vanadium catalyst and oxygen as the terminal oxidant, dimers with an ortho-ortho' coupling pattern were obtained with high selectivity. Further oxidation led to ortho'-ortho' coupling to generate a tetramer, which provided insight that the atropisomerization barriers of the unsymmetrical biaryl bonds are much lower than expected.
• ORGANOMETALLIC COMPOUND, ORGANIC LIGHT-EMITTING DEVICE INCLUDING ORGANOMETALLIC COMPOUND, AND DIAGNOSTIC COMPOSITION INCLUDING ORGANOMETALLIC COMPOUND
  申请人：Samsung Electronics Co., Ltd.

  公开号：US20200354393A1

  公开（公告）日：2020-11-12

  An organometallic compound represented by Formula 1, an organic light-emitting device including the organometallic compound, and a diagnostic composition including the organometallic compound: M 11 (L 11 ) n11 (L 12 ) n12 Formula 1 wherein, in Formula 1, M 11 is a first-row transition metal, a second-row transition metal, or a third-row transition metal, L 11 is a ligand represented by Formula 1-1, L 12 is a monodentate ligand or a bidentate ligand, n11 is 1, and n12 is 0, 1, or 2: wherein, in Formula 1-1, Y 11 , A 11 , T 11 k11, k12, k13, b11, E 11 to E 13 and R 11 to R 17 are described in the specification, and *1 to *4 each independently indicate a binding site to M 11 .

  一种由公式1表示的有机金属化合物，包括该有机金属化合物的有机发光器件，以及包括该有机金属化合物的诊断组成物：M11（L11）n11（L12）n12公式1其中，在公式1中，M11是第一行过渡金属、第二行过渡金属或第三行过渡金属，L11是由公式1-1表示的配体，L12是单齿配体或双齿配体，n11为1，n12为0、1或2：其中，在公式1-1中，Y11、A11、T11、k11、k12、k13、b11、E11到E13和R11到R17在规范中描述，*1到*4分别独立表示与M11的结合位点。