2-(2-trimethylsilyl-1-ethynyl)-3-quinolinecarbaldehyde | 307966-35-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-(2-trimethylsilyl-1-ethynyl)-3-quinolinecarbaldehyde
• 英文别名: 2-(2-(trimethylsilyl)ethynyl)quinoline-3-carbaldehyde；2-((trimethylsilyl)ethynyl)quinoline-3-carbaldehyde；2-(trimethylsilanyl)ethynylquinoline-3-carbaldehyde；2-(trimethylsilylethynyl)quinoline-3-carbaldehyde；2-trimethylsilylethynylquinoline-3-carboxaldehyde；2-(trimethylsilanylethynyl)quinoline-3-carbaldehyde；2-(2-trimethylsilylethynyl)quinoline-3-carbaldehyde
• CAS: 307966-35-4
• 化学式: C₁₅H₁₅NOSi
• 分子量: 253.376
• InChiKey: NSSALDSMTOHYHC-UHFFFAOYSA-N

物化性质

• 熔点：
  88-89 °C
• 沸点：
  369.0±42.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.28
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2-trimethylsilyl-1-ethynyl)-3-quinolinecarbaldehyde 在 sodium chlorite 、 sodium dihydrogenphosphate dihydrate 、 双氧水 作用下， 以 水 、 叔丁醇 为溶剂， 反应 4.0h， 以64%的产率得到3-(trimethylsilanyl)pyrano[4,3-b]quinolin-1-one
  参考文献：
  名称：

  由2-炔基-3-甲酰基喹啉经氧化6-内-挖-环封闭一锅合成吡喃并[4,3- b ]喹啉酮

  摘要：

  一个新的区域选择性一个-一锅法合成pyranoquinolinones从容易获得的2-炔基-3- formylquinolines温和的NaClO下2 / H 2 ö 2以良好的收率的条件已探索。该反应顺序，涉及氧化随后区域选择性电6-内-挖环化是在传统的Pd（0）介导的合成更有效。当使用无清除剂的条件时，获得了不寻常的氯化呋喃喹啉酮衍生物。

  DOI：

  10.1016/j.tetlet.2011.11.016
• 作为产物：
  描述：

  N-乙酰苯胺 在 bis-triphenylphosphine-palladium(II) chloride 、 三乙胺 、 三苯基膦 、 三氯氧磷 作用下， 以 乙腈 为溶剂， 反应 10.0h， 生成 2-(2-trimethylsilyl-1-ethynyl)-3-quinolinecarbaldehyde
  参考文献：
  名称：

  Convenient synthesis of benzo[b]pyrazolo[5,1-f][1,6]naphthyridines by silver triflate catalyzed three-component reaction of 2-alkynyl-3-formylquinolines, tosylhydrazine and carbonyl compounds

  摘要：

  Benzo[b]pyrazolo[5,1-f][1,6]naphthyridines were prepared by silver triflate catalyzed one-pot cyclization of tosylhydrazine, carbonyl compounds and 2-alkynyl-3-formylquinolines, which are available by Sonogashira reaction of 2-chloro-3-formylquinoline. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.02.060

文献信息

• A New Route to Acridines: Pauson-Khand Reaction on Quinoline-Bearing 1-En-7-ynes Leading to Novel Tetrahydrocyclopenta[<i>c</i>]acridine-2,5-diones
  作者：Philippe Belmont、Amaury Patin

  DOI：10.1055/s-2005-870016

  日期：——

  Efficient Pauson-Khand reactions on quinolines bearing 1-en-7-ynes features gave tetrahydrocyclopenta[c]acridine derivatives. The quinoline intermediates were obtained in two steps: a Sonogashira reaction with functionalized alkynes (TMS, Bu, Ph, CHB 2 OTHP) followed by a Grignard reaction with allylmagnesium bromide. The sequence provides new acridine structures in four high yielding steps from commercially

  对具有 1-en-7-ynes 特征的喹啉进行有效的 Pauson-Khand 反应得到四氢环戊二烯 [c] 吖啶衍生物。喹啉中间体分两步获得：与官能化炔烃（TMS、Bu、Ph、CHB 2 OTHP）的 Sonogashira 反应，然后与烯丙基溴化镁的格氏反应。该序列在四个高产步骤中从市售的喹啉中提供了新的吖啶结构。
• An efficient synthesis of indol-3-yl benzonaphthyridines via copper(II) triflate-catalyzed heteroannulation
  作者：K.S. Prakash、Rajagopal Nagarajan

  DOI：10.1016/j.tetlet.2013.04.106

  日期：2013.7

  An efficient and convenient method for the synthesis of indol-3-yl benzo[b][1,6]- and benzo[c][2,7]naphthyridines via copper(II) triflate-catalyzed heteroannulation is reported. This method gives new analogues of indole containing benzonaphthyridines from easily accessible starting materials. This reaction proceeds under mild conditions.

  报道了一种通过三氟甲磺酸铜（II）催化杂环化合成吲哚-3-基苯并[ b ] [1,6]-和苯并[ c ] [2,7]萘吡啶的有效简便方法。该方法从易于获得的起始原料中得到了含有吲哚的新吲哚类似物。该反应在温和的条件下进行。
• Tandem furo[3,4-b]pyridine formation—Diels–Alder reaction: an approach to the synthesis of nitrogen containing heterocyclic analogues of 1-arylnaphthalene lignans
  作者：Gouranga P. Jana、Binay K. Ghorai

  DOI：10.1016/j.tet.2007.09.007

  日期：2007.11

  derivatives has been examined. The reaction affords furo[3,4-b]pyridine as transient intermediates; the latter undergo [4+2] cycloaddition with an electron-deficient dienophile. Acid/base-induced ring opening of the exo-cycloadducts followed by aromatization give substituted quinolines related to heterocyclic analogues of 1-arylnaphthalene lignans. An intramolecular variant of this protocol is also

  已经研究了费歇尔卡宾配合物与2-炔基-3-吡啶羰基衍生物的偶联。反应得到呋喃并[3,4- b ]吡啶作为过渡中间体。后者与缺电子的亲双烯体进行[4 + 2]环加成反应。酸/所述的碱诱导的环开口外-cycloadducts随后芳构给予取代的喹啉与1- arylnaphthalene木脂杂环类似物。该方案的分子内变体也可通过使用未活化的烯基系链来实现。然而，桥接的环加合物在经历自发开环以产生醇时是可溶的。该方法对于呋喃[3,4- b]喹啉中间体首次出现，可被双亲亲虫捕获。
• Multicomponent Approach for the Synthesis of Phenanthridine and Acridine Ring Systems via the Coupling of Fischer Carbene Complexes with Hetero­aromatic o-Alkynyl Carbonyl Derivatives
  作者：Binay Ghorai、Gouranga Jana、Soumita Mukherjee

  DOI：10.1055/s-0030-1258180

  日期：2010.9

  phenanthridine and acridine derivatives is described. This method includes the in situ generation of furo[3,4-c]isoquinoline and furo[3,4-b]quinoline intermediates by the coupling of heteroaromatic o-alkynyl carbonyl derivatives with Fischer carbene complexes and subsequent trapping of these intermediates by suitable dienophiles. azaisobenzofuran - heterocycles - Diels-Alder reaction - chromium - carbene complexes

  描述了菲啶和a啶衍生物的一锅多组分合成。该方法包括通过杂芳族邻炔基羰基衍生物与菲舍尔卡宾配合物的偶联原位生成呋喃[3,4- c ]异喹啉和呋喃[3,4- b ]喹啉中间体，然后通过适当的方法捕获这些中间体双亲物。 氮杂异苯并呋喃-杂环-Diels-Alder反应-铬-卡宾配合物
• Efficient Base-Catalyzed 5-<i>exo</i>-dig Cyclization of Carbonyl Groups on Unactivated Alkynyl-Quinolines: An Entry to Versatile Oxygenated Heterocycles Related to the Furoquinoline Alkaloids Family
  作者：Philippe Belmont、Thomas Godet、Johann Bosson

  DOI：10.1055/s-2005-918953

  日期：——

  An efficient 5-exo-dig cyclization was observed when TMS-protected alkynyl-quinolines bearing a carbonyl group were submitted to a mixture of an alcohol (alkyl-OH, diol, amino alcohol) with an inorganic base (K2CO3). The cyclization process seems to go through the deprotection of the TMS group prior to the ­cyclization step. The dihydrofuroquinoline derivatives formed are structurally related to the well-known furoquinoline alkaloids family. The scope and limitations of this reaction have also been studied with diverse bases and various alkynyl and carbonyl derivatives.

  当含有酮基的TMS保护炔基喹啉与醇（烷基醇、二醇、氨基醇）和无机碱（K2CO3）混合时，观察到一种高效的5-exo-dig环化反应。环化过程似乎通过TMS基团的去保护步骤，然后再进行环化。所形成的二氢呋喃喹啉衍生物在结构上与著名的呋喃喹啉生物碱家族有关。该反应的范围和局限性也已通过不同的碱和各种炔基及羰基衍生物进行了研究。