3-(cyclopropylethynyl)pyridine | 1221793-76-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-(cyclopropylethynyl)pyridine
• 英文别名: 3-(2-cyclopropylethynyl)pyridine
• CAS: 1221793-76-5
• 化学式: C₁₀H₉N
• 分子量: 143.188
• InChiKey: JTAIHZOZJLZELR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(cyclopropylethynyl)pyridine 、 2-甲氧基-1,4-萘醌 以 苯 为溶剂， 以86%的产率得到1-cyclopropyl-2a-methoxy-2-pyridin-3-yl-8aH-cyclobuta[b]naphthalene-3,8-dione
  参考文献：
  名称：

  Small molecular inhibitors of miR-1 identified from photocycloadducts of acetylenes with 2-methoxy-1,4-naphthalenequinone

  摘要：

  Small molecules which can modulate endogenous microRNAs are important chemical tools to study microRNA regulational network. In this Letter we screened the [2+2] photocycloadducts of 2-methoxy-1,4-naphthalenequinone with a series of aryl acetylenes on their activity to modulate endogenous microRNAs. A potent inhibitor of the muscle-specific miR-1 which is closely related with cardiac development and disease was identified. The small molecular inhibitor was the cyclobutene type product derived from the photocycloaddition of 2-methoxy-1,4-naphthalenequinone with tert-butyl (5-(phenylethynyl) quinolin-8-yl) carbonate. Analogues of the small molecular inhibitor were then prepared using similar photocycloaddition reactions for evaluation on inhibition activity on miR-1 to provide structure-activity relationship of the miR-1 inhibitor. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.04.058
• 作为产物：
  描述：

  3-Cyclopropyl-1-pyridin-3-ylprop-2-yn-1-one 在 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 乙基苯 为溶剂， 反应 48.0h， 以45%的产率得到3-(cyclopropylethynyl)pyridine
  参考文献：
  名称：

  Rh 催化碳-炔键活化共轭炔酮脱羰：通过 DFT 计算进行反应范围和机理探索

  摘要：

  在这篇完整的文章中，详细描述了共轭单炔酮催化脱羰合成二取代炔烃的进展。反应范围和局限性已被彻底研究，并且......

  DOI：

  10.1039/c5sc00584a

文献信息

• CsF-Mediated in Situ Desilylation of TMS-Alkynes for Sonogashira Reaction
  作者：Joseph S. Capani、John E. Cochran、Jianglin (Colin) Liang

  DOI：10.1021/acs.joc.9b01307

  日期：2019.7.19

  A practical and mild set of conditions for the Sonogashira reaction utilizing CsF-mediated in situ TMS-alkyne desilylation followed by Sonogashira coupling has been developed for the synthesis of a variety of alkynyl benzenes and heteroarenes in good to excellent yields. This methodology demonstrates excellent functional group tolerance and simple purification, which allows large-scale industrial applications

  利用CsF介导的原位TMS-炔基甲硅烷基化和随后的Sonogashira偶联，已为Sonogashira反应开发了一套实用且温和的条件，以良好的收率合成了各种炔基苯和杂芳烃。该方法论证明了出色的官能团耐受性和简单的纯化方法，可用于大规模工业应用。这一一锅协议可避免挑战性的游离炔分离，从而实现高产Sonogashira与挥发性炔的偶联。
• Photoinduced Tandem Reactions of Isoquinoline-1,3,4-trione with Alkynes To Build Aza-polycycles
  作者：Haitao Yu、Jinbo Li、Zhuangfei Kou、Xuewen Du、Yi Wei、Hoong-Kun Fun、Jianhua Xu、Yan Zhang

  DOI：10.1021/jo100218w

  日期：2010.5.7

  Photoinduced tandem reactions of isoquinoline-1,3,4-triones (3) with azaaryl substituted acetylenes (4a−4o) are described as an efficient method to build novel aza-polycycles. Most of the reactions proceeded via the tandem reaction sequence of photoinduced [2 + 2] cycloaddition (the Paterno−Büchi reaction)-oxetene electrocyclic ring opening-hexatriene to phenanthrene type electrocyclization-oxidative

  异喹啉-1,3,4-三酮（3）与氮杂芳基取代的乙炔（4a - 4o）的光诱导串联反应被描述为构建新型氮杂多环化合物的有效方法。大多数反应是通过光诱导的[2 + 2]环加成反应（Paterno-Büchi反应）-氧杂环丁烯电环开环-己三烯至菲型电环化-氧化脱氢的串联反应顺序。使用异喹啉三酮与被吡啶，嘧啶，吡嗪和喹啉等不同氮杂芳基环取代的乙炔进行的这些光串联反应，我们能够获得各种杂多氮杂多环骨架，其中异喹啉二酮与萘，喹啉或异喹啉，喹唑啉，喹喔啉和苯并菲合，产率分别高达85％。讨论了[2 + 2]光环加成反应的区域选择性和反应顺序中导致形成不同的氮杂-多环系统的电环化反应。
• A bench-stable reagent for C-4 selective deuteriodifluoromethylation of azines
  作者：Junqing Liang、Lefeng Dong、Feng Qian、Yijin Kong、Mingxia Wang、Xiaoyong Xu、Xusheng Shao、Zhong Li

  DOI：10.1016/j.cclet.2022.01.085

  日期：2022.11

  for selectivity deuteriodifluoromethylation of azines with a high deuterium incorporation yield. The late-stage modification of complex molecules further confirmed the potential of this reagent for practical applications. We expect that our reagent to find applications in synthesis of isotope-labelled molecules of interests for drug-discovery and related ilucidation of mechanism of action.

  氘二氟甲基 (CF 2 D) 是一个具有挑战性且重要的官能团，因为氘掺入困难且缺乏有效的前体试剂。在此，我们报告了一种来自廉价氘源的稳定试剂氘二氟甲基膦 (DDFP)，用于以高氘掺入产率对吖嗪进行选择性氘二氟甲基化。复杂分子的后期修饰进一步证实了该试剂在实际应用中的潜力。我们希望我们的试剂能够在合成同位素标记的感兴趣分子中找到应用，以进行药物发现和相关作用机制的阐明。
• A universal activator of microRNAs identified from photoreaction products
  作者：Xuejiao Chen、Chengmei Huang、Wenjie Zhang、Yihan Wu、Xi Chen、Chen-yu Zhang、Yan Zhang

  DOI：10.1039/c2cc32157b

  日期：——

  A small molecule activator of microRNAs has been identified from photoreaction products of naphthalene-1,4-dione with acetylenes and the universal activation on miRNAs was realized through significant promotion on the processing of precursor microRNAs by the compound.

  从萘-1,4-二酮与乙炔的光反应产物中发现了一种小分子 microRNA 激活剂，通过该化合物对前体 microRNA 处理的显著促进作用，实现了对 miRNA 的普遍激活。
• Rh-catalyzed decarbonylation of conjugated ynones via carbon–alkyne bond activation: reaction scope and mechanistic exploration via DFT calculations
  作者：Alpay Dermenci、Rachel E. Whittaker、Yang Gao、Faben A. Cruz、Zhi-Xiang Yu、Guangbin Dong

  DOI：10.1039/c5sc00584a

  日期：——

  In this full article, detailed development of a catalytic decarbonylation of conjugated monoynones to synthesize disubstituted alkynes is described. The reaction scope and limitation has been thoroughly investigated, and a...

  在这篇完整的文章中，详细描述了共轭单炔酮催化脱羰合成二取代炔烃的进展。反应范围和局限性已被彻底研究，并且......