7-chloro-5H-pyrido[3,2-b]indole | 1310693-44-7

• 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: 7-chloro-5H-pyrido[3,2-b]indole
• CAS: 1310693-44-7
• 化学式: C₁₁H₇ClN₂
• 分子量: 202.643
• InChiKey: DERHFNCDCOVOHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  7-chloro-5H-pyrido[3,2-b]indole 在 2-双环己基膦-2',6'-二甲氧基联苯 、 potassium phosphate 、 tris-(dibenzylideneacetone)dipalladium(0) 、 sodium hydride 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成
  参考文献：
  名称：

  有机电致发光材料及其器件

  摘要：

  公开了一种有机电致发光材料及其器件。所述有机电致发光材料是一种新型三芳胺‑氮杂咔唑喹唑啉类化合物。这些化合物可用作电致发光器件中的主体材料，并能提供更好的器件性能。

  公开号：

  CN111675707B
• 作为产物：
  描述：

  N-(3-chlorophenyl)pyridin-3-amine 在 palladium diacetate 、 三氟乙酸 、 氨 作用下， 以 水 为溶剂， 反应 6.0h， 以39%的产率得到7-chloro-5H-pyrido[3,2-b]indole
  参考文献：
  名称：

  δ-Carbolines and their ring-opened analogs: Synthesis and evaluation against fungal and bacterial opportunistic pathogens

  摘要：

  Previous studies have indicated that the delta-carboline (2) ring system derived from the natural product cryptolepine (1) may represent a pharmacophore for anti-infective activity. This paper describes the design and synthesis of a small library of substituted delta-carbolines and the evaluation of the anti-fungal and anti-bacterial activities. An evaluation of the anti-bacterial activity of a previously reported library of ring-opened analogs was also conducted to provide an opportunity to test the hypothesis that both group of compounds may have the same biological target. Results indicate that against a selected group of fungal pathogens, substituted delta-carbolinium analogs displayed higher potency and several fold lower cytotoxicity than cryptolepine the parent natural product. Both the delta-carbolinium compounds and their ring-opened analogs, exhibited equally high anti-bacterial activity against the selected pathogens and especially against the gram positive bacteria evaluated. Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2011.03.021

文献信息

• Biphilic Organophosphorus-Catalyzed Intramolecular C_sp²–H Amination: Evidence for a Nitrenoid in Catalytic Cadogan Cyclizations
  作者：Trevor V. Nykaza、Antonio Ramirez、Tyler S. Harrison、Michael R. Luzung、Alexander T. Radosevich

  DOI：10.1021/jacs.7b13803

  日期：2018.2.28

  equiv of phosphetane P-oxide 3·[O] and 2-nitrosobiphenyl. Experimental and computational investigations into the C-N bond forming event suggest the involvement of an oxazaphosphirane (2 + 1) adduct between 3 and 2-nitrosobiphenyl, which evolves through loss of phosphetane P-oxide 3·[O] to give the observed carbazole product via C-H insertion in a nitrene-like fashion.

  小环磷杂环烷烃 (1,2,2,3,4,4-六甲基膦烷, 3) 在氢硅烷末端还原剂存在下催化分子内 CN 键形成邻硝基联芳基和苯乙烯基衍生物的杂环化。该方法在操作简单的均相有机催化条件下提供了对各种咔唑和吲哚化合物的可扩展访问，如在 1 g 规模上进行的 17 个例子所证明的那样。原位 NMR 反应监测研究支持涉及催化 PIII/PV=O 循环的机制，其中三配位磷化合物 3 代表催化静止状态。对于邻硝基联苯催化转化为咔唑，确定了膦烷催化剂 3（一级）、底物（一级）和苯基硅烷（零级）的动力学反应顺序。对于差异 5-取代的 2-硝基联苯，通过吸电子取代基（哈米特因子 ρ = +1.5）加速转化，这与速率决定步骤中硝基底物上负电荷的累积一致。周转限制脱氧事件的 DFT 建模表明，磷烷催化剂 3 和 2-硝基联苯底物之间的速率决定性 (3 + 1) 螯合加成形成未观察到的五配位螺-双环二恶氮磷烷，其通过
• Solvent-free synthesis of δ-carbolines/carbazoles from 3-nitro-2-phenylpyridines/2-nitrobiphenyl derivatives using DPPE as a reducing agent
  作者：Haixia Peng、Xuxing Chen、Yanhong Chen、Qian He、Yuyuan Xie、Chunhao Yang

  DOI：10.1016/j.tet.2011.06.027

  日期：2011.8

  A green and efficient preparation of functionalized delta-carbolines/carbazoles via reductive ring closure by 1,2-bis(dipenylphosphino)ethane under solvent-free conditions is described. The starting materials 3-nitro-2-phenylpyridines/2-nitrobiphenyl derivatives are readily prepared through Suzuki-Miyaura cross-coupling reaction from commercially available compounds. And the polar by-product ethane-1,2-diylbis(diphenylphosphine oxide) is easily removed from the relatively polar reaction mixture. Various substituted delta-carbolines/carbazoles are obtained in acceptable yields. It is particularly worth mentioning that substrates with electron-withdrawing groups (EWG) also give the desired products in good yield. (C) 2011 Elsevier Ltd. All rights reserved.
• δ-Carbolines and their ring-opened analogs: Synthesis and evaluation against fungal and bacterial opportunistic pathogens
  作者：Tryphon K. Mazu、Jagan R. Etukala、Melissa R. Jacob、Shabana I. Khan、Larry A. Walker、Seth Y. Ablordeppey

  DOI：10.1016/j.ejmech.2011.03.021

  日期：2011.6

  Previous studies have indicated that the delta-carboline (2) ring system derived from the natural product cryptolepine (1) may represent a pharmacophore for anti-infective activity. This paper describes the design and synthesis of a small library of substituted delta-carbolines and the evaluation of the anti-fungal and anti-bacterial activities. An evaluation of the anti-bacterial activity of a previously reported library of ring-opened analogs was also conducted to provide an opportunity to test the hypothesis that both group of compounds may have the same biological target. Results indicate that against a selected group of fungal pathogens, substituted delta-carbolinium analogs displayed higher potency and several fold lower cytotoxicity than cryptolepine the parent natural product. Both the delta-carbolinium compounds and their ring-opened analogs, exhibited equally high anti-bacterial activity against the selected pathogens and especially against the gram positive bacteria evaluated. Published by Elsevier Masson SAS.
• 有机电致发光材料及其器件
  申请人：北京夏禾科技有限公司

  公开号：CN111675707B

  公开（公告）日：2023-06-06

  公开了一种有机电致发光材料及其器件。所述有机电致发光材料是一种新型三芳胺‑氮杂咔唑喹唑啉类化合物。这些化合物可用作电致发光器件中的主体材料，并能提供更好的器件性能。