2-(3,3-dimethyl-1-butynyl)-N-(triphenylphosphonylidene)benzeneamine | 207278-63-5

• 英文名称: 2-(3,3-dimethyl-1-butynyl)-N-(triphenylphosphonylidene)benzeneamine
• 英文别名: [2-(3,3-dimethylbut-1-ynyl)phenyl]imino-triphenyl-λ5-phosphane
• CAS: 207278-63-5
• 化学式: C₃₀H₂₈NP
• 分子量: 433.533
• InChiKey: HIIOWGRIMXRLJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.89
• 重原子数：
  32.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  12.36
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2-(3,3-dimethyl-1-butynyl)-N-(triphenylphosphonylidene)benzeneamine 在 silver trifluoromethanesulfonate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 9.58h， 生成 (E)-1-(2-tert-butyl-1H-indol-1-yl)-N-propylpropan-1-imine
  参考文献：
  名称：

  Lewis Acid-Catalyzed or Base-Promoted Regioselective Cycloisomerization ofN-Imidoyl-o-alkynylanilines for Synthesis ofN-Imidoyl-(1 H)-indoles and 4-Alkylidene-3,4-dihydroquinazolines

  摘要：

  AbstractProduct selectivity control for the synthesis of imidoylindoles and 4‐alkylidenedihydroquinazolines from N‐imidoyl‐o‐alkynylanilines via silver triflate‐catalyzed cycloisomerization or tetrabutylammonium fluoride‐promoted cyclization is described. The product selectivity depends mainly on the catalyst/promoter used, and on the substituents on the alkyne and amidine functions of the substrates.magnified image

  DOI：

  10.1002/adsc.201401186
• 作为产物：
  描述：

  2-(3,3-二甲基丁-1-炔基)苯胺 、 二溴三苯基膦 在 三乙胺 作用下， 以86%的产率得到2-(3,3-dimethyl-1-butynyl)-N-(triphenylphosphonylidene)benzeneamine
  参考文献：
  名称：

  Generation of Biradicals and Subsequent Formation of Quinolines and 5H-Benzo[b]carbazoles from N-[2-(1-Alkynyl)phenyl]ketenimines

  摘要：

  DOI：

  10.1021/jo9804285

文献信息

• Triflic acid-promoted cycloisomerization of 2-alkynylphenyl isothiocyanates and isocyanates: a novel synthetic method for a variety of indole derivatives
  作者：Takao Saito、Yoshihiko Sonoki、Takashi Otani、Noriki Kutsumura

  DOI：10.1039/c4ob00825a

  日期：——

  A new approach towards the synthesis of indole derivatives via triflic acid-promoted cycloisomerization with rearrangement of 2-(alkyn-1-yl)phenyl isothiocyanates and 2-(alkyn-1-yl)phenyl isocyanates has been achieved. By this methodology, structurally diverse types of indole derivatives such as thieno- and furo-indoles, spiro-indolethiones, spiro-oxindoles, and 3-alkylidene-oxindoles were synthesized

  已经实现了通过三氟甲磺酸促进的环异构化并重排2-（炔-1-基）苯基异硫氰酸酯和2-（炔-1-基）苯基异氰酸酯来合成吲哚衍生物的新方法。通过这种方法，合成了结构上不同类型的吲哚衍生物，例如噻吩-和呋喃-吲哚，螺-吲哚硫酮，螺-羟吲哚和3-亚烷基-氧吲哚。
• Thiocarbonyl induced heterocumulenic Pauson–Khand type reaction: expedient synthetic method for thieno[2,3-b]indol-2-ones
  作者：Takao Saito、Hiroshi Nihei、Takashi Otani、Toshiyuki Suyama、Naoki Furukawa、Masatoshi Saito

  DOI：10.1039/b712739a

  日期：——

  The first examples of CS induced Pauson–Khand type reactions are described; 2-alkynylphenyl isothiocyanates were converted to 3-substituted-2H-thieno[2,3-b]indol-2-ones in the presence of a stoichiometric amount of Mo(CO)6 or Co2(CO)8, or a catalytic amount of Rh catalyst under an atmospheric pressure of carbon monoxide.

  首次描述了由CS诱导的Pauson–Khand类型反应；2-烷基炔基苯异硫氰酸酯在摩尔比为1的Mo(CO)6或Co2(CO)8的存在下，或在碳 monoxide气氛下使用催化量的Rh催化剂，转化为3取代的2H-噻吩[2,3-b]吲哚-2-酮。
• Biradicals from Thermolysis of <i>N</i>-[2-(1-Alkynyl)phenyl]-<i>N</i>‘-phenylcarbodiimides and Their Subsequent Transformations to 6<i>H</i>-Indolo[2,3-<i>b</i>]quinolines
  作者：Chongsheng Shi、Quan Zhang、Kung K. Wang

  DOI：10.1021/jo981845k

  日期：1999.2.1

  Thermolysis of the carbodiimide 9a in gamma-terpinene at 138 degrees C produced 2-(phenylamino)quinoline (11a, 49%) and the parent 6H-indolo[2,3-b]quinoline (14a, 16%). Apparently, 11a was produced via the biradical 10a followed by hydrogen-atom abstraction from gamma-terpinene. A two-step biradical pathway through 12a or a one-step intramolecular Diels-Alder reaction could furnish 13a, which then

  碳二亚胺9a在138℃下在γ-萜品烯中的热解产生2-（苯氨基）喹啉（11a，49％）和母体6H-吲哚并[2,3-b]喹啉（14a，16％）。显然，通过双自由基10a生成11a，然后从γ-萜品烯中提取氢原子。通过12a的两步双自由基途径或一个分子内Diels-Alder反应一步可提供13a，然后将其进行互变异构化得到14a。对于在乙炔基末端具有三甲基甲硅烷基取代基的碳二亚胺9b，在138℃下在回流的对二甲苯中热解仅产生6H-吲哚并[2，3-b]喹啉14b（86％）。在回流的乙醇中用6 N NaOH处理14b，然后以92％的收率得到14a。类似地，通过碳二亚胺9c-f的热解获得6H-吲哚并[2,3-b]喹啉14c-f。通过使用4-甲氧基苯基异氰酸酯与亚氨基膦酸酯2d和2f之间的氮杂-维蒂希反应来产生相应的碳二亚胺，然后进行热分解，得到在C上具有甲氧基取代基的6H-吲哚并[2，3-b]喹啉16d和16f。
• TfOH-promoted transformation from 2-alkynylphenyl isothiocyanates to quinoline-2-thiones or indoles
  作者：Takashi Otani、Shinichi Kunimatsu、Taku Takahashi、Hiroshi Nihei、Takao Saito

  DOI：10.1016/j.tetlet.2009.04.045

  日期：2009.7

  A variety of 4-arylquinoline-2-thiones and 3-arylthieno[2,3-b]indoles were synthesized in high yields via TfOH-promoted tandem Friedel-Crafts alkenylation-cyclization reactions of 2-alkynylphenyl isothiocyanates. (c) 2009 Elsevier Ltd. All rights reserved.