2-(hex-1-yn-1-yl)quinoline-3-carbaldehyde | 868765-10-0

• 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-(hex-1-yn-1-yl)quinoline-3-carbaldehyde
• 英文别名: 2-Hex-1-ynylquinoline-3-carbaldehyde；2-hex-1-ynylquinoline-3-carbaldehyde
• CAS: 868765-10-0
• 化学式: C₁₆H₁₅NO
• 分子量: 237.301
• InChiKey: WQPPUUCGEQIEQT-UHFFFAOYSA-N

物化性质

• 沸点：
  416.5±30.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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-(hex-1-yn-1-yl)quinoline-3-carbaldehyde 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79%的产率得到3-butylpyrano[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：

  1-己炔 在 bis-triphenylphosphine-palladium(II) chloride 、 三乙胺 作用下， 生成 2-(hex-1-yn-1-yl)quinoline-3-carbaldehyde
  参考文献：
  名称：

  Silver-Catalyzed Tandem Synthesis of Naphthyridines and Thienopyridines via Three-Component Reaction

  摘要：

  An efficient approach for the silver-catalyzed regioselective tandem synthesis of highly functionalized 1,2-dihydorbenzo[1,6]naphthyridines 6a-z and 7a-e by the reaction of ortho-alkynylaldehydes 3a-n with amines 4a-d and ketones 5a-c/active methylene compounds 5d-g, under mild reaction conditions, is described. The scope of the developed chemistry was successfully extended for the direct synthesis of 1,2-dihydorbenzo[4,5]thieno[2,3-c]pyridines 8a-e, which is known as the sulfur analogue of beta-carbolines. Naphthyridines 6a-z and thienopyridines 8a-e were obtained via dual activation concept using L-proline as organocatalyst; however, naphthyridines 7a-e were synthesized without using organocatalyst. The reaction shows selective N-C bond formation on the more electrophilic alkynyl carbon, resulting in the regioselective 6-endo-digcyclized products. Reactivity behavior of electron-deficient and electron-rich ortho-alkynylaldehydes in the synthesis of naphthyridines and thienopyridine by three-component reaction is supported by the control experiment.

  DOI：

  10.1021/jo400400c

文献信息

• Formation of Condensed 1<i>H</i>-Pyrrol-2-ylphosphonates and 1,2-Dihydropyridin-2-ylphosphonates via Kabachnik–Fields Reaction of Acetylenic Aldehydes and Subsequent 5-<i>exo</i>-<i>dig</i> or 6-<i>endo</i>-<i>dig</i> Cyclizations
  作者：Rita Bukšnaitienė、Aurelija Urbanaitė、Inga Čikotienė

  DOI：10.1021/jo501011u

  日期：2014.7.18

  Kabachnik–Fields reactions of various carbocyclic or heterocyclic acetylenic aldehydes together with subsequent Lewis acid catalyzed cyclizations have been studied. It was found that 5-exo-dig versus 6-endo-dig cyclization mode strongly depends on the structure of starting materials. Thus, nonaromatic acetylenic α-anilinomethylphosphonates underwent gold(III)-catalyzed or iodine-mediated 5-exo-dig

  研究了各种碳环或杂环炔醛的Kabachnik-Fields反应以及随后的路易斯酸催化的环化反应。发现5- exo - dig与6- endo - dig环化模式在很大程度上取决于起始材料的结构。因此，非芳族炔属α-苯胺基甲基膦酸酯经历了金（III）催化或碘介导的5- exo - dig环化成1 H-吡咯-2-基膦酸酯。与此相反，吸电子的杂芳族的基体构成通过专用6-含材料-1,2-二氢吡啶-2- ylphosphonate环内-挖闭环过程。仅对于含有苯环的α-氨基（2-炔基苯基）甲基膦酸酯，双环化是可能的。
• Site-Selective Electrophilic Cyclization and Subsequent Ring-Opening: A Synthetic Route to Pyrrolo[1,2-<i>a</i>]quinolines and Indolizines
  作者：Trapti Aggarwal、Sonu Kumar、Devendra K. Dhaked、Rakesh K. Tiwari、Prasad V. Bharatam、Akhilesh K. Verma

  DOI：10.1021/jo3015374

  日期：2012.10.5

  An efficient strategy for the synthesis of pyrrolo[1,2-a]quinolines and indolizines from pyranoquinolines via site-selective electrophilic cyclization and subsequent opening of pyran ring using silver/iodine under mild reaction conditions is described. This approach involves the preferential attack of the pyridyl nitrogen over aryl ring and leads to the formation of 5-endo-dig cyclized products. Quantum

  描述了一种通过位点选择性亲电环化从吡喃并喹啉合成吡咯并[1,2- a ]喹啉和吲哚嗪的有效策略，随后在温和的反应条件下使用银/碘打开吡喃环。这种方法涉及的吡啶基的氮的优先攻击过的芳环，并导致5-地层内切-挖环化产物。C–N（ΔE a = 9.01 kcal / mol）和C–C（ΔE a为了使观察到的位点选择性合理化，进行＝ 31.31kcal / mol）的键形成。通过X射线晶体学研究证实了产物的结构。通过Pd催化的交叉偶联反应，通过亲电碘化反应生成的碘取代的化合物进一步多样化。
• 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。
• Silver-catalyzed regioselective synthesis of acridines, quinolines, and naphthalenes from 3-(2-alkynyl)aryl-β-ketoesters
  作者：Satya Prakash Shukla、Rakesh Tiwari、Akhilesh Kumar Verma

  DOI：10.1016/j.tet.2012.08.068

  日期：2012.11

  general synthetic method for a wide range of medicinally useful 2-carboxylate derivatives of acridinols, quinolinols, and naphthalenols has been developed via silver-catalyzed electrophilic cyclization of 3-(2-alkynyl)aryl-β-ketoesters. The designed reaction involved selective C–C bond formation on more electrophilic alkynyl carbon, which resulted in the regioselective 6-endo-dig cyclized product, as confirmed

  通过银催化的3-（2-炔基）芳基-β-酮酸酯的亲电子环化反应，已经开发了一种简便，有效且通用的合成方法，用于各种医学上有用的a啶醇，喹啉醇和萘酚的2-羧酸酯衍生物。所设计的反应涉及在多个电子炔基碳选择性C-C键的形成，这就造成了区域选择性6-内-挖环化产物，通过X射线晶体学研究证实。进行氘标记实验以支持所提出的机制。合成方法可适应炔烃上广泛的官能团变异，这对结构和生物活性评估非常有利。
• Study on the Reactions of Acetylenic Aldehydes with Dimethyl Phosphite in Basic Media: Phosphonate-Phosphate Rearrangement<i>versus</i>5-<i>exo</i>-dig Cyclization Reactions
  作者：Inga Cikotiene、Rita Buksnaitiene

  DOI：10.1002/adsc.201200276

  日期：2012.10.8

  Tandem reactions of various acetylenic aldehydes with dimethyl phosphite in basic media were investigated. It was shown that in the case of a non-activated triple bond of the starting materials, the well-known Pudovik reaction followed by a subsequent phosphonate-phosphate rearrangement took place. On the other hand when the triple bond of the starting materials is activated by electron-withdrawing

  在碱性介质中研究了各种炔醛与亚磷酸二甲酯的串联反应。已经表明，在起始材料的未活化的三键的情况下，发生了众所周知的Pudovik反应，随后发生了膦酸酯-磷酸盐的重排。另一方面，当起始材料的三键被吸电子杂环激活时，顺畅且区域选择性的串联5-外切-环化反应成为可能。

表征谱图