2-(4-trimethylsilyl-1,3-butadiyn-1-yl)aniline | 164471-64-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(4-trimethylsilyl-1,3-butadiyn-1-yl)aniline
• 英文别名: 2-(4-Trimethylsilylbuta-1,3-diynyl)aniline
• CAS: 164471-64-1
• 化学式: C₁₃H₁₅NSi
• 分子量: 213.354
• InChiKey: ABBJNWMLDJTXCI-UHFFFAOYSA-N

物化性质

• 沸点：
  308.0±44.0 °C(predicted)
• 密度：
  1.01±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(4-trimethylsilyl-1,3-butadiyn-1-yl)aniline 在 copper(l) chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以50%的产率得到2,2'-(buta-1,3-diyne-1,4-diyl)bis(1H-indole)
  参考文献：
  名称：

  A straightforward synthesis of indole and benzofuran derivatives

  摘要：

  A new methodology for the synthesis of indole and benzofuran derivatives has been devised. The starting materials, ortho-substituted aryl diynes, have been easily converted into new unsaturated bis-indolyl and bis-benzofuran derivatives and into 2-ethynylindole and 2-ethynylbenzofuran. Both these products have been further elaborated into more complex unsaturated indole-benzofuran and bis-benzofuran derivatives. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.10.100
• 作为产物：
  描述：

  2-氨基苯乙炔 、 三甲基乙炔基硅 在 四甲基乙二胺 、 copper(l) chloride 作用下， 以 丙酮 为溶剂， 以56%的产率得到2-(4-trimethylsilyl-1,3-butadiyn-1-yl)aniline
  参考文献：
  名称：

  铜催化末端1,3-二炔和叠氮化物对炔基或烯丙基亚酰胺和亚酰胺的选择性

  摘要：

  描述了末端的1，3-二炔与缺电子的叠氮化物的铜催化反应以生成3-炔基或2，3-二烯基亚酰胺和酰亚胺。选择性取决于二炔取代基和与相应三唑前体生成的酮丁酰亚胺中间体反应的亲核试剂。含有炔丙基乙酸酯的1,3-二炔反应生成[3]枯烯基亚酰胺，而使用甲醇作为捕集剂的反应选择性生成2,3-二烯基酰亚胺。从含有均丙基羟基或胺取代基的1，3-二炔获得五元杂环。

  DOI：

  10.1021/acs.orglett.0c03861

文献信息

• Consecutive Gold(I)-Catalyzed Cyclization Reactions of <i>o</i>-(Buta-1,3-diyn-1-yl-)-Substituted <i>N</i>-Aryl Ureas: A One-Pot Synthesis of Pyrimido[1,6-<i>a</i>]indol-1(2<i>H</i>)-ones and Related Systems
  作者：Phillip P. Sharp、Martin G. Banwell、Jens Renner、Klaas Lohmann、Anthony C. Willis

  DOI：10.1021/ol4007986

  日期：2013.6.7

  Treatment of readily available o-(buta-1,3-diyn-1-yl-)-substituted N-aryl ureas such as 1 with the Au(I)-catalyst 11 affords, via a twofold cyclization process, the isomeric pyrimido[1,6-a]indol-1(2H)-one 3 in good yield.
• Synthesis of Isocoumarins from o-Iodobenzoic Acid and Terminal Acetylenes Mediated by Palladium Complexes and Zinc Chloride
  作者：Hong-Yueh Liao、Chien-Hong Cheng

  DOI：10.1021/jo00117a023

  日期：1995.6

  o-Iodobenzoic acid (1) reacts with various terminal acetylenes (HC=CR) in the presence of Pd(PPh(3))(4), Et(3)N, and ZnCl2 in DMF to give the corresponding 3-substituted isocoumarins (C6H4COOC(R)CH: R = n-C4H9 (2a); n-C3H7 (3a); CH2OCH3 (4a); C(CH3)(2)OH (5a); CH2OH (6a); C6H5 (7a);p-CH3C6H4 (8a); 1-cyclohexenyl (9a); o-NH2C6H4 (10a)) in fair to excellent yields, In some of these catalytic reactions, substituted isocoumarin b (C6H4COOC(R)C(C=CR)) and alkylidenephthalide c were isolated in a few percent yields, Under similar conditions, treatment of 1 with a trimethylsilyl 1,3-diyne 12 led to the formation of products 3-(2-indolyl)isocoumarin (13) and an indolylphthalide 14 in a 95:5 ratio. The reaction of o-1-pentynylbenzoic acid with ZnCl2 and Et(3)N gave 3a as the sole product indicating that ZnCl2 is likely responsible for the selective formation of the six-membered isocoumarin ring, Based on this observation and the known palladium chemistry, a mechanism involving the participation of palladium complexes in the alkynylation of 1 and zinc chloride in the heteroannulation of the reaction intermediate o-1-alkynylbenzoate is proposed for the present catalytic reactions.
• A rapid synthesis of 2-alkynylindoles and 2-alkynylbenzofurans
  作者：Vito Fiandanese、Daniela Bottalico、Giuseppe Marchese、Angela Punzi

  DOI：10.1016/j.tet.2008.05.059

  日期：2008.7

  An expeditious synthesis of 2-alkynylindoles and 2-alkynylbenzofuran derivatives has been devised starting from easily available ortho-substituted aryl diynes. (c) 2008 Elsevier Ltd. All rights reserved.
• Copper-catalyzed tandem reaction between imines and alcohols leading to indoles
  作者：Shin Kamijo、Yuya Sasaki、Yoshinori Yamamoto

  DOI：10.1016/j.tetlet.2003.10.141

  日期：2004.1

  A copper-catalyzed tandem reaction between 2-alkynyl-N-arylideneanilines and alcohols is found to produce N-(alkoxybenzyl)indoles in good to high yields. A wide variety of substituted N-(alkoxybenzyl)indole derivatives call be synthesized by utilizing this protocol, since the derived indoles are essentially formed by the four-component assemblies of aldehydes, 2-iodoanilines, terminal alkynes, and alcohols. (C) 2003 Elsevier Ltd. All rights reserved.