(E)-9-[2-(phenyl)ethenyl]-9H-carbazole | 95249-64-2

• 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: (E)-9-[2-(phenyl)ethenyl]-9H-carbazole
• 英文别名: 9-[(E)-2-phenylethenyl]-9H-carbazole；trans-N-(2-phenylvinyl)carbazole；(E)-N-(2-phenylvinyl)carbazole；N-(2-phenylethylenyl)carbazole；(E)-9-styryl-9H-carbazole；N-(E)-styrylcarbazole；Gmgclydlykiali-ccezhusrsa-；9-[(E)-2-phenylethenyl]carbazole
• CAS: 95249-64-2
• 化学式: C₂₀H₁₅N
• 分子量: 269.346
• InChiKey: GMGCLYDLYKIALI-CCEZHUSRSA-N

物化性质

• 熔点：
  116-120 °C (decomp)
• 沸点：
  450.0±28.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  N-乙烯基咔唑 在 tris-(dibenzylideneacetone)dipalladium(0) 、 氯化(双三环己基膦)(一氧化碳)(氢)钌 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 44.0h， 生成 (E)-9-[2-(phenyl)ethenyl]-9H-carbazole
  参考文献：
  名称：

  Highly Stereoselective Synthesis, Structure, and Application of (E)-9-[2-(Silyl)ethenyl]-9H-carbazoles

  摘要：

  通过一种新型催化剂途径(silylative偶联), (E)-N-(Silyl)vinylcarbazole被容易制备。该偶联反应由鲁西配位化合物[RuH(Cl)(CO)(PCy3)(2)]催化的二元组乙烯与三元组硅烷的silylative偶联反应制备。二元组硝基NC-vinylcarbazole和一元组石英基NC-vinylcarbazole两种硝基NC-vinylcarbazole的crystal结构已被精确测定。通过二元组硝基NC-vinylcarbazole制备的(E)-N-(triethoxysilyl)vinylcarbazole，随后对该中间化合物进行碘苯的Hiyama亲电取代反应(作为偶联反应配合物的联合作用状况)。在此催化体系下，所合成的(E)-N-(triethoxysilyl)vinylcarbazole与碘苯在Pdstartswith催化下协同反应，开环反应得到(E)-N-(phenylvinyl)carbazole，产率高达77.5%且高度保留立体选择性。

  DOI：

  10.1021/jo051629t

文献信息

• 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。
• Ethanol as a Hydrogenating Agent: Palladium-Catalyzed Stereoselective Hydrogenation of Ynamides To Give Enamides
  作者：Alla Siva Reddy、K. C. Kumara Swamy

  DOI：10.1002/anie.201702277

  日期：2017.6.6

  as a hydrogenating agent for ynamides under palladium catalysis. This behavior is different from the normally expected reaction of ethanol addition to alkynes. The reaction shows stereoselectivity for E enamides, which is in contrast to reports using other hydrogenating sources. The method was also extended to ynamines. Alternatively, the use of ethanol and ammonium formate as the hydrogenating source

  乙醇在钯催化下可作为乙酰胺的氢化剂。此行为与通常将乙醇加成炔烃的预期反应不同。该反应显示出对E 烯酰胺的立体选择性，这与使用其他氢化源的报道相反。该方法还扩展到了ynamines。或者，使用乙醇和甲酸铵作为氢化源得到Z- 酰胺。通过氘标记实验证明了乙醇在氢化反应中的作用。
• A new route to N-substituted heterocycles
  作者：Alan R. Katritzky、Hengyuan Lang、Xiangfu Lan

  DOI：10.1016/s0040-4020(01)80382-3

  日期：1993.4

  -carbazole, and -benzimidazole, and analogs substituted in the methylene group are converted by lithium aluminum hydride, or by Grignard reagents, or in two cases by organozinc reagents, into the N-substituted heterocycles in good yields.

  N-（苯并三唑-1-基甲基）-吲哚，吡咯，-咔唑和-苯并咪唑以及在亚甲基中取代的类似物通过氢化铝锂，格氏试剂或两种情况下的有机锌试剂转化为N-取代的杂环具有良好的收率。
• METHOD FOR PRODUCING FLUORINE-CONTAINING OLEFIN
  申请人：Asahi Glass Company, Limited

  公开号：US20160176791A1

  公开（公告）日：2016-06-23

  A method for producing at least one compound selected from the group consisting of a compound represented by the following formula (10), a compound represented by the following formula (11), a compound represented by the following formula (12), and a compound represented by the following formula (13), which the method containing reacting a compound represented by the following formula (2) with a compound represented by the following formula (7), in the presence of at least one compound selected from the group consisting of a compound represented by the following formula (1), a compound represented by the following formula (3), a compound represented by the following formula (4), a compound represented by the following formula (8), and a compound represented by the following formula (9).

  一种生产以下式子所表示的化合物中至少一种的方法（其中，式子（10）表示的化合物，式子（11）表示的化合物，式子（12）表示的化合物和式子（13）表示的化合物），该方法包含在以下式子（2）所表示的化合物和以下式子（7）所表示的化合物在以下式子（1）所表示的化合物、以下式子（3）所表示的化合物、以下式子（4）所表示的化合物、以下式子（8）所表示的化合物和以下式子（9）所表示的化合物中至少选择一种存在的情况下反应。
• Method for producing fluorine-containing olefin
  申请人：ASAHI GLASS COMPANY, LIMITED

  公开号：US10421702B2

  公开（公告）日：2019-09-24

  A method for producing at least one compound selected from the group consisting of a compound represented by the following formula (10), a compound represented by the following formula (11), a compound represented by the following formula (12), and a compound represented by the following formula (13), which the method containing reacting a compound represented by the following formula (2) with a compound represented by the following formula (7), in the presence of at least one compound selected from the group consisting of a compound represented by the following formula (1), a compound represented by the following formula (3), a compound represented by the following formula (4), a compound represented by the following formula (8), and a compound represented by the following formula (9).

  一种生产至少一种选自由下式(10)代表的化合物、下式(11)代表的化合物、下式(12)代表的化合物和下式(13)代表的化合物组成的组的化合物的方法，该方法包括使下式(2)代表的化合物与下式(7)代表的化合物反应、在至少一种选自由下式 (1) 所代表的化合物、下式 (3) 所代表的化合物、下式 (4) 所代表的化合物、下式 (8) 所代表的化合物和下式 (9) 所代表的化合物组成的组中的化合物存在的情况下。

表征谱图