9-(1-propenyl)carbazole | 3324-18-3

• 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: 9-(1-propenyl)carbazole
• 英文别名: N-(1-propenyl)carbazole；9-prop-1-enylcarbazole
• CAS: 3324-18-3
• 化学式: C₁₅H₁₃N
• 分子量: 207.275
• InChiKey: SFQDJUABNNSJHB-UHFFFAOYSA-N

物化性质

• 沸点：
  346.6±15.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

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：

  methyl phenylselenomalonitrile 、 9-(1-propenyl)carbazole 在 偶氮二异丁腈 作用下， 以 苯 为溶剂， 反应 24.0h， 生成 anti-(2-(N-carbazolyl)-2-(phenylseleno)-1-methylethyl)methylpropanedinitrile 、 syn-(2-(N-carbazolyl)-2-(phenylseleno)-1-methylethyl)methylpropanedinitrile
  参考文献：
  名称：

  Group Transfer Addition Reactions of Methyl (phenylseleno)malononitrile to Alkenes

  摘要：

  Results of a detailed study of group transfer additions of methyl(phenylseleno)propanedinitrile (4) to a wide variety of alkenes are reported. For example, heating of 4 (60 degrees C) with 1-hexene and AIBN produces (2-(phenylseleno)-hexyl)methylpropanedinitrile in 97% yield. Reagent 4 adds in high yields to monosubstituted styrenes, enol ethers, enol acetates, enol sulfides, enamides, and enol imidazoles and carbazoles. Additions to many classes of 1,2-disubstituted alkenes also occur, and modest to good levels of 1,2-asymmetric induction are observed in the selenium transfer step. Oxygen- and sulfur-substituted alkenes produce anti products, and N-substituted alkenes produce syn products. The proposed mechanism involves radical addition followed by phenylselenium group transfer, and it is shown that radical additions to certain classes of disubstituted alkenes can be reversible. Additions to trisubstituted alkenes fair, probably because of this reversibility. Competition studies provide a relative reactivity scale of alkenes toward the electrophilic methylpropanedinitrile radical. Finally, a series of transformations serve to illustrate some synthetic possibilities for the products of these selenium transfer addition reactions.

  DOI：

  10.1021/ja00089a017
• 作为产物：
  描述：

  9-allyl-9H-carbazole 在 [RuHCl(CO)(PPh₃)₃] 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 以97%的产率得到9-(1-propenyl)carbazole
  参考文献：
  名称：

  通过烯丙基化合物的串联异构化为乙烯基衍生物和将腈类化合物的腈类化合物进行1,3-偶极环加成反应，方便地合成异恶唑啉

  摘要：

  通过将QCH（X）CHCH（Y）串联异构化为QC（X）CHCH 2（Y）（Q = RO，RS，R 2 N，R 3 Si等; X ＝ H，R，OR； Y ＝ H，R； R ＝烷基，芳基）被钌配合物催化，并且提出了后者化合物的1，3-偶极环加成成芳族腈氧化物。还描述了QCH（X）CHCH（Y）与2,6-二氯苄腈氧化物的环加成。讨论了氮氧化物与烯丙基和1-丙烯基（通常为乙烯基）化合物的环加成反应的区域选择性和立体选择性。

  DOI：

  10.1016/j.tetlet.2008.07.176
• 作为试剂：
  描述：

  trans-9-propenylcarbazole 、 甲醇 在 9-(1-propenyl)carbazole 作用下， 以 二氯甲烷 为溶剂， 反应 0.05h， 以a yield of 0.25 g (50%) was obtained的产率得到9-(1-propenyl)carbazole
  参考文献：
  名称：

  Oligomeric and polymeric photosensitizers

  摘要：

  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。

  公开号：

  US20020025991A1

文献信息

• Ｎ−ビニルアゾール類の製造方法
  申请人：学校法人日本大学

  公开号：JP2015137227A

  公开（公告）日：2015-07-30

  【課題】有機エレクトロルミネッセンス、電子写真感光体、有機半導体、太陽電池等の機能性化合物の原料モノマーとして有用なＮ−ビニルアゾール類を高収率かつ経済的に得る方法を提供する。【解決手段】アゾール類とハロゲン化ビニル類とをパラジウム化合物及びリン系配位子の存在下、塩基としてＮａＯＨを用いて反応させることにより、高収率かつ高選択的にＮ−ビニルアゾール類を得る方法を用いる。【選択図】なし

  提供一种高收率且经济有效地获得作为有机电致发光、电子感光体、有机半导体、太阳能电池等功能性化合物原料单体中有用的N-乙烯基唑类化合物的方法。通过在钯化合物和磷系配位子存在下，使用NaOH作为碱，使唑类化合物和卤代乙烯类化合物反应，从而高收率且高选择性地获得N-乙烯基唑类化合物的方法。【选定图】无
• 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。
• N-(trans-1-Propenyl)carbazole: an excellent dienophile for cation radical Diels–Alder cycloadditions
  作者：Daxin Gao、Nathan L Bauld

  DOI：10.1016/s0040-4039(00)01046-7

  日期：2000.8

  The efficient, regiospecific, and periselective Diels-Alder cycloadditions of N-(trans-1-propenyl)carbazole, a highly electron rich dienophile, to both acyclic and cyclic conjugated dienes is found to be induced by tris(4-bromophenyl)aminium hexachloroantimonate. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Group Transfer Addition Reactions of Methyl (phenylseleno)malononitrile to Alkenes
  作者：Dennis P. Curran、Eugen Eichenberger、Maree Collis、Michael G. Roepel、Gebhard Thoma

  DOI：10.1021/ja00089a017

  日期：1994.5

  Results of a detailed study of group transfer additions of methyl(phenylseleno)propanedinitrile (4) to a wide variety of alkenes are reported. For example, heating of 4 (60 degrees C) with 1-hexene and AIBN produces (2-(phenylseleno)-hexyl)methylpropanedinitrile in 97% yield. Reagent 4 adds in high yields to monosubstituted styrenes, enol ethers, enol acetates, enol sulfides, enamides, and enol imidazoles and carbazoles. Additions to many classes of 1,2-disubstituted alkenes also occur, and modest to good levels of 1,2-asymmetric induction are observed in the selenium transfer step. Oxygen- and sulfur-substituted alkenes produce anti products, and N-substituted alkenes produce syn products. The proposed mechanism involves radical addition followed by phenylselenium group transfer, and it is shown that radical additions to certain classes of disubstituted alkenes can be reversible. Additions to trisubstituted alkenes fair, probably because of this reversibility. Competition studies provide a relative reactivity scale of alkenes toward the electrophilic methylpropanedinitrile radical. Finally, a series of transformations serve to illustrate some synthetic possibilities for the products of these selenium transfer addition reactions.
• Convenient synthesis of isoxazolines via tandem isomerization of allyl compounds to vinylic derivatives and 1,3-dipolar cycloaddition of nitrile oxides to the vinylic compounds
  作者：Stanisław Krompiec、Piotr Bujak、Wojciech Szczepankiewicz

  DOI：10.1016/j.tetlet.2008.07.176

  日期：2008.10

  effective method for the synthesis of new isoxazolines via tandem isomerization of QCH(X)CHCH(Y) to QC(X)CHCH2(Y) (Q = RO, RS, R2N, R3Si, etc.; X = H, R, OR; Y = H, R; R = alkyl, aryl) catalyzed by ruthenium complexes and 1,3-dipolar cycloaddition of the latter compounds to arenenitrile oxides is presented. The cycloaddition of QCH(X)CHCH(Y) to 2,6-dichlorobenzonitrile oxide is also described. The regio-

  通过将QCH（X）CHCH（Y）串联异构化为QC（X）CHCH 2（Y）（Q = RO，RS，R 2 N，R 3 Si等; X ＝ H，R，OR； Y ＝ H，R； R ＝烷基，芳基）被钌配合物催化，并且提出了后者化合物的1，3-偶极环加成成芳族腈氧化物。还描述了QCH（X）CHCH（Y）与2,6-二氯苄腈氧化物的环加成。讨论了氮氧化物与烯丙基和1-丙烯基（通常为乙烯基）化合物的环加成反应的区域选择性和立体选择性。