1-乙基-2-乙炔苯 | 75659-49-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-乙基-2-乙炔苯
• 英文名称: 1-ethyl-2-ethynylbenzene
• CAS: 75659-49-3
• 化学式: C₁₀H₁₀
• 分子量: 130.189
• InChiKey: AXGGKLZJFFAHEK-UHFFFAOYSA-N

物化性质

• 沸点：
  195.2±19.0 °C(Predicted)
• 密度：
  0.92±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-乙基-2-乙炔苯 在 platinum(II) chloride 作用下， 以 甲苯 为溶剂， 反应 22.0h， 以99%的产率得到甲茚
  参考文献：
  名称：

  Platinum and Ruthenium Chloride-Catalyzed Cycloisomerization of 1-Alkyl-2-ethynylbenzenes: Interception of π-Activated Alkynes with a Benzylic C−H Bond

  摘要：

  Air-stable and commercially available alkynophilic metal salts, such as PtCl2, PtCl4, and [RuCl2(CO)(3)](2), catalyze the cycloisomerization of 1-alkyl-2-ethynylbenzenes to produce Substituted indenes even at all ambient temperature. Electrophilically activated alkynes can be intercepted by simple benzylic C-H bonds at primary, secondary, and tertiary carbon centers. Mechanistic studies, such as labeling studies and kinetic isotope and substituent effects, indicate that the cycloisomerization proceeds through the formation of a vinylidene intermediate and turnover-limiting 1,5-shift of benzylic hydrogen.

  DOI：

  10.1021/jo901045g
• 作为产物：
  描述：

  [(2-乙基苯基)乙炔基](三甲基)硅烷 在 potassium fluoride 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以80%的产率得到1-乙基-2-乙炔苯
  参考文献：
  名称：

  Rational Design of 4-Aryl-1,2,3-Triazoles for Indoleamine 2,3-Dioxygenase 1 Inhibition

  摘要：

  Indoleamine 2,3-dioxygenase 1 (IDO1) is an important therapeutic target treatment of diseases such as cancer that involve pathological immune escape. Starting from the scaffold of our previously discovered IDO1 inhibitor 4-phenyl-1,2,3-triazole, we used computational structure-based methods to design more potent ligands. This approach yielded highly efficient low molecular weight inhibitors, the most active being of nanomolar potency both in an enzymatic and in a cellular assay, while showing no cellular toxicity and a high selectivity for IDO1 over tryptophan 2,3-dioxygenase (TDO). A quantitative structure-activity relationship based on the electrostatic ligand-protein interactions in the docked binding modes and on the quantum chemically derived charges of the triazole ring demonstrated a good explanatory power for the observed activities.

  DOI：

  10.1021/jm300260v

文献信息

• Synthesis of 1 <i>H</i> ‐Pyrrolo[1,2‐ <i>a</i> ]indoles <i>via</i> Lewis Acid‐Catalyzed Annulation of Propargylic Alcohols with 2‐Ethynylanilines
  作者：Li‐Juan Du、Ya‐Ping Han、Hong‐Yu Zhang、Yuecheng Zhang、Jiquan Zhao、Yong‐Min Liang

  DOI：10.1002/adsc.201901409

  日期：2020.3.17

  A novel highly efficient, environmentally benign Lewis acid‐catalyzed, and protection‐free protocol for the construction of valuable polycyclic products bearing a 1H‐pyrrolo[1,2‐a]indole scaffold is described, starting from readily available propargylic alcohols and 2‐ethynylanilines. The one‐pot transformation entails the cleavage of one C−O bond, and the construction of two C−N bonds and one C−C

  描述了一种新型的高效，环境友好的路易斯酸催化且无保护的方案，用于构建带有1 H-吡咯并[1,2- a ]吲哚骨架的有价值的多环产物，从容易获得的炔丙醇和2开始乙炔基苯胺。一锅转换需要裂解一个C-O键，两个C-N键和一个C-C双键。这种独特的操作简单的方法是在温和条件下和空气中进行的，产生的水是唯一的副产物。它具有可伸缩性，并显示出良好的功能组兼容性和广泛的适用范围。
• Lewis Acid‐Catalyzed Formal [3+3] Annulation of Propargylic Alcohols with 4‐Hydroxy‐2 <i>H</i> ‐chromen‐2‐ones
  作者：Ya‐Ping Han、Xue‐Song Li、Ming Li、Xin‐Yu Zhu、Yong‐Min Liang

  DOI：10.1002/adsc.201800131

  日期：2018.8.6

  tricyclic compounds possessing functionalized pyrano[3,2‐c]chromen‐5(2H)‐one fragments has been developed using propargylic alcohols and 4‐hydroxy‐2H‐chromen‐2‐ones as the substrates. The protocol provides a one‐step, environmentally benign method of accessing a broad range of pyrano[3,2‐c]chromen‐5(2H)‐one derivatives in excellent yields under mild conditions and with good functional‐group tolerance. The method

  一种路易斯酸催化的正式[3 + 3]级联环化策略，用于形成具有官能化吡喃并[3,2-c] chromen-5（2 H）-一个片段的各种三环化合物，已使用炔丙醇和4-羟基2 H-铬2-2作为底物。该协议提供了一种在环境温和的条件下以良好的收率和良好的官能团耐受性来访问范围广泛的吡喃并[3,2-c] chromen-5（2 H）-one衍生物的一步法，对环境无害的方法。该方法在克规模上是有效的，这突出了这种合成转化的固有实用性。
• Brønsted Acid‐Mediated Formal [3+3] Annulation Between Propargylic Alcohols and 1,3‐Diketones
  作者：Ya‐Ping Han、Xue‐Song Li、Xin‐Yu Zhu、Zhou Sun、Ming Li、Yu‐Zhao Wang、Yong‐Min Liang

  DOI：10.1002/adsc.201701296

  日期：2018.3

  A Brønsted acid‐mediated formal [3+3] cascade annulation of propargylic alcohols with 1,3‐diketones proceeds through a sequential Meyer−Schuster rearrangement/1,2‐addition. This protocol, which has a wide scope and is conducted under an ambient atmosphere, enables access to a broad array of valuable chromenone derivatives related to many natural products in satisfactory yields under mild conditions

  布朗斯台德酸介导的带有1,3-二酮的炔丙醇的正式[3 + 3]级联环化反应通过顺序的Meyer-Schuster重排/ 1,2-加成进行。该方案具有广泛的适用范围，并且在环境气氛下进行，可以在温和的条件下以令人满意的产率获得与许多天然产物有关的有价值的色酮衍生物。该方法可以按比例缩放至克级，这突出了此转换的潜在适用性。
• Lewis Acid‐Catalyzed [4+2] Annulation between Propargylic Alcohols with Benzo[ <i>d</i> ]isoxazoles
  作者：Ya‐Ping Han、Xue‐Song Li、Zhou Sun、Xin‐Yu Zhu、Ming Li、Xian‐Rong Song、Yong‐Min Liang

  DOI：10.1002/adsc.201700495

  日期：2017.8.17

  An unprecedented copper(II) trifluoromethanesulfonate‐catalyzed [4+2] cascade annulation of propargylic alcohols with benzo[d]isoxazoles proceeds through a sequential ring opening/Meyer–Schuster rearrangement/intermolecular cyclization. This protocol, which tolerates a broad variety of functional groups, offers a versatile, modular and atom‐economical access to a new class of fascinating quinoline

  前所未有的三氟甲磺酸铜（II）催化的炔丙醇与苯并[ d ]异恶唑的级联环化反应通过顺序开环/ Meyer-Schuster重排/分子间环化来进行。该方案可耐受多种官能团，在温和条件下以高收率提供了一种通用的，模块化的，原子经济的途径来获得新型迷人的喹啉衍生物。转换可以有效地放大到克级，从而突出了此方法的综合效用。
• Lewis Acid‐Catalyzed Annulation of Propargylic Alcohols with ( <i>Z</i> )‐2‐Styryl‐1 <i>H</i> ‐Indoles
  作者：Xue‐Song Li、Ya‐Ping Han、Xin‐Yu Zhu、Yu Xia、Wan‐Xu Wei、Ming Li、Yong‐Min Liang

  DOI：10.1002/adsc.201800907

  日期：2018.11.16

  A novel copper(II) trifluoromethanesulfonate‐catalyzed intermolecular cascade annulation strategy for the construction of a great variety of pentacyclic compounds possessing valuable carbazole fragments was developed employing propargylic alcohols and (Z)‐2‐styryl‐1H‐indoles as the initial substrates. This protocol, which entails a sequential Meyer‐Schuster rearrangement/isomerization/‐cyclization

  以丙醇和（Z）-2-苯乙烯基-1H-吲哚为初始底物，开发了一种新颖的三氟甲磺酸铜（II）催化的分子间级联环化策略，用于构建多种具有有价值的咔唑片段的五环化合物。该方案需要进行连续的Meyer-Schuster重排/异构化/环化级联反应，可在温和条件下轻松，原子经济地获得具有宽泛官能团耐受性的五环化合物，并具有良好的收率。转换可以有效地按比例放大至克数量，从而加重了这项工作的潜在应用范围。

表征谱图