trans-9-propenylcarbazole | 20566-00-1

• 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: trans-9-propenylcarbazole
• 英文别名: N-(trans-1-propenyl)carbazole；9-[(E)-prop-1-enyl]carbazole
• CAS: 20566-00-1
• 化学式: C₁₅H₁₃N
• 分子量: 207.275
• InChiKey: SFQDJUABNNSJHB-BIIKFXOESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  trans-9-propenylcarbazole 在 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 生成 cis-9-propenylcarbazole
  参考文献：
  名称：

  9-Alkenylcarbazoles. 6. Synthesis and structure of cis-9-propenylcarbazoles

  摘要：

  DOI：

  10.1007/bf02401721
• 作为产物：
  描述：

  咔唑 在 吡啶 、 盐酸 、 乙酰氯 作用下， 以 1,4-二氧六环 、 苯 为溶剂， 反应 24.5h， 生成 trans-9-propenylcarbazole
  参考文献：
  名称：

  The Cation Radical Chain Cycloaddition Polymerization of N,3-Bis(trans-1-propenyl)carbazole: The Critical Importance of Intramolecular Hole Transfer in Cation Radical Cycloaddition Polymerization

  摘要：

  The synthesis and polymerization of N,3-[bis (trans-1-propenyl)] carbazole (1) is reported. Using either the stable cation radical salt tris(4-bromophenyl)aminium hexachloroantimonate (2(+.)) or anodic oxidation to initiate the reaction, novel cycloaddition polymers are obtained in which the intermonomer linkages are of the cyclobutane, and to some extent of the Diels-Alder, type. A novel cation radical chain mechanism is proposed for the reaction, and extensive support for this mechanism is presented. The greatly enhanced reactivity of difunctional, as opposed to monofunctional, substrates in cation radical cycloadditions is dramatically highlighted by a comparison of the cycloaddition reactivity (rapid polymerization) of 1 versus N-propenylcarbazole (inefficient cyclodimerization) under electrochemical oxidation conditions. The sharply enhanced reactivity of 1 is attributed to the availability of intramolecular hole transfer in the bifunctional but not the monofunctional case.

  DOI：

  10.1002/1615-4169(200107)343:5<481::aid-adsc481>3.3.co;2-j

文献信息

• Host–Guest-Induced Electron Transfer Triggers Radical-Cation Catalysis
  作者：Rebecca L. Spicer、Athanasios D. Stergiou、Tom A. Young、Fernanda Duarte、Mark D. Symes、Paul J. Lusby

  DOI：10.1021/jacs.9b11273

  日期：2020.2.5

  principle of capsule catalysis. Here we show an alternative strategy, wherein catalytic activation of otherwise inactive quinone "co-factors" by a simple Pd2L4 capsule pro-motes a range of bulk-phase, radical-cation cycloadditions. Solution electron transfer experiments and cyclic voltammetry show the cage anodically shifts the redox potential of the encapsulated quinone by a significant 1 V. Moreover, the

  通过封装改变底物的反应性是胶囊催化的基本原理。在这里，我们展示了一种替代策略，其中通过简单的 Pd2L4 胶囊催化活化原本不活跃的醌“辅因子”，促进了一系列本体相、自由基阳离子环加成。溶液电子转移实验和循环伏安法显示笼子使封装的醌的氧化还原电位阳极移动了 1 V。此外，胶囊还保护还原的半醌免受质子化，从而将醌的作用从化学计量氧化剂转化为催化单电子接受者。我们设想主客体诱导的“电子空穴”释放将转化为各种形式的非封装催化，涉及其他难以处理的，
• Palladium-Catalyzed Stereocontrolled Vinylation of Azoles and Phenothiazine
  作者：Artyom Y. Lebedev、Vyatcheslav V. Izmer、Denis N. Kazyul'kin、Irina P. Beletskaya、Alexander Z. Voskoboynikov

  DOI：10.1021/ol0172370

  日期：2002.2.1

  with vinyl bromides catalyzed by palladium-phosphine complexes results in the respective N-vinylazoles in 30-99% yields. This reaction with cis- and trans-beta-bromostyrenes is stereospecific giving the respective products with full retention of configuration.

  [反应：见正文]钯-膦配合物催化的各种吡咯（吡咯，吲哚，咔唑及其衍生物）和吩噻嗪与乙烯基溴的乙烯基化反应产生相应的N-乙烯基唑，产率为30-99％。与顺式和反式-β-溴苯乙烯的反应是立体定向的，从而使各个产物具有完全保留的构型。
• Oligomeric and polymeric photosensitizers
  申请人：——

  公开号：US20020025991A1

  公开（公告）日：2002-02-28

  Enhancement of the rates of cationic polymerizations initiated by onium salts has been achieved through the use of oligomeric and polymeric electron-transfer photosensitizers derived from a polymerizable compound substituted with a polynuclear aromatic group, including epoxides, oxetanes, and ethylenically unsaturated compounds. The polymerizable compound is substituted with residues derived from anthracene, naphthalene, perylene, pyrene, fluorene, carbazole, indole, benzocarbazole, acridone, phenothiazine, and thianthrene, particularly carbazole.

  通过使用由可聚合化合物取代的多核芳香基团衍生的寡聚物和聚合物电子转移光敏剂，包括环氧化物、氧杂环丙烷和乙烯基不饱和化合物，已经实现了由离子型盐引发的阳离子聚合速率的提高。可聚合化合物被取代为来自蒽、萘、苝、芘、芴、咔唑、吲哚、苯并咔唑、芴酮、苯并噻吩的残基，特别是咔唑。
• Oligomeric and polymeric photosensitizers comprising a polynuclear aromatic group
  申请人：Renssealer Polytechnic Institute

  公开号：US06593388B2

  公开（公告）日：2003-07-15

  Enhancement of the rates of cationic polymerizations initiated by onium salts has been achieved through the use of oligomeric and polymeric electron-transfer photosensitizers derived from a polymerizable compound substituted with a polynuclear aromatic group, including epoxides, oxetanes, and ethylenically unsaturated compounds. The polymerizable compound is substituted with residues derived from anthracene, naphthalene, perylene, pyrene, fluorene, carbazole, indole, benzocarbazole, acridone, phenothiazine, and thianthrene, particularly carbazole.

  通过使用由可聚合化合物衍生的富含多核芳香基团的寡聚物和聚合物电子转移光敏剂，包括环氧化物、氧杂环戊烷和乙烯不饱和化合物，已经实现了由离子盐引发的阳离子聚合反应速率的提高。可聚合化合物被取代为来自蒽、萘、苝、芘、芴、咔唑、吲哚、苯并咔唑、吖啶酮、苯并噻吩和噻吩的残基，特别是咔唑。
• Radiation polymerisable compositions having accelerated cure
  申请人：——

  公开号：US20040044094A1

  公开（公告）日：2004-03-04

  A radiation polymerisable composition comprising: (A) a donor/acceptor component for forming a charge transfer complex said component being selected from the group consisting of: (i) a bifunctional compound having an electron donor group and an electron withdrawing group and a polymerisable unsaturated group; (ii) a mixture of (a) at least one unsaturated compound having an electron donor group and a polymerisable unsaturated moiety; and (b) at least one unsaturated compound having an electron acceptor group and a polymerisable unsaturated group; and (B) a Lewis acid.

  一种可辐射聚合的组合物，包括： (A) 用于形成电荷转移络合物的供体/受体组分，所述组分选自由以下组别组成(i) 具有电子供体基团、电子汲取基团和可聚合不饱和基团的双官能团化合物； (ii) (a) 至少一种具有电子供体基团和可聚合不饱和基团的不饱和化合物；和 (b) 至少一种具有电子受体基团和可聚合不饱和基团的不饱和化合物的混合物；以及 (B) 路易斯酸。