5-(4-methoxy-phenyl)-pent-1-yn-3-ol

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-(4-methoxy-phenyl)-pent-1-yn-3-ol
• 英文别名: 5-(4-Methoxyphenyl)pent-1-yn-3-ol
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: QHORVQUUXJJLHB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(4-methoxy-phenyl)-pent-1-yn-3-ol 在 bismuth(lll) trifluoromethanesulfonate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 1.0h， 以77%的产率得到1-甲基-7-甲氧基-2-萘满酮
  参考文献：
  名称：

  Synthesis of 2-tetralone derivatives by Bi(OTf)3-catalyzed intramolecular hydroarylation/isomerization of propargyl alcohols

  摘要：

  Compared to 1-tetralones, 2-tetralones are expensive, less stable, and difficult to synthesize. A concise Bi-catalyzed method was developed for the synthesis of 2-tetralones from 5-phenylpent-1-yn-3-ol derivatives. Diverse 2-tetralones were obtained in moderate to good yields under mild conditions. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.12.129
• 作为产物：
  描述：

  4-甲氧基肉桂酸 在 lithium aluminium tetrahydride 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 5-(4-methoxy-phenyl)-pent-1-yn-3-ol
  参考文献：
  名称：

  Synthesis of 2-tetralone derivatives by Bi(OTf)3-catalyzed intramolecular hydroarylation/isomerization of propargyl alcohols

  摘要：

  Compared to 1-tetralones, 2-tetralones are expensive, less stable, and difficult to synthesize. A concise Bi-catalyzed method was developed for the synthesis of 2-tetralones from 5-phenylpent-1-yn-3-ol derivatives. Diverse 2-tetralones were obtained in moderate to good yields under mild conditions. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.12.129

文献信息

• Rhodium‐Catalyzed Parallel Kinetic Resolution of Racemic Internal Allenes Towards Enantiopure Allylic 1,3‐Diketones
  作者：Lukas J. Hilpert、Bernhard Breit

  DOI：10.1002/anie.201903365

  日期：2019.7.15

  parallel kinetic resolution of racemic 1,3‐disubstituted allenes by means of a rhodium‐catalyzed addition to 1,3‐diketones furnishing enantiopure allylic 1,3‐diketones is described. Mechanistic experiments demonstrate that the different allene enantiomers react in parallel to either the diastereomeric E‐ or Z‐allylic 1,3‐diketones with the same absolute configuration of the newly formed stereogenic

  描述了一种罕见的情况，即通过铑催化向1,3-二酮中添加外消旋的1,3-二取代的烯类，同时提供对映体纯的烯丙基1,3-二酮。机理实验表明，不同的丙二烯对映异构体与非对映异构体E-或Z-烯丙基1,3-二酮平行反应，且具有与新形成的立体异构中心相同的绝对构型。广泛的底物范围证明了这种新方法的综合实用性。
• Transition-Metal-Free Synthesis of Electron Rich 1,3-Dienes via Base Promoted Isomerization of Propargylic Ethers
  作者：Chunxiang Liu、Guogang Deng、Xin Li、Yiren Xu、Kaili Yu、Wen Chen、Hongbin Zhang、Xiaodong Yang

  DOI：10.1002/ejoc.201901743

  日期：2020.1.31

  An efficient and broadly applicable method for the construction of functionalized electron rich 1,3‐dienes through a base promoted isomerization reaction of propargylic ethers is presented. This process features easy handling reaction conditions, transition‐metal‐free isomerization, high isolated yields, and most of all, it could be used for late stage modification of natural products.

  提出了一种通过炔丙基醚的碱促进的异构化反应来构建官能化的富电子的1,3-二烯的有效方法。该工艺具有易于处理的反应条件，无过渡金属的异构化，高分离产率的特点，最重要的是，它可用于天然产物的后期改性。
• A New Ruthenium-Catalyzed Cleavage of a Carbon−Carbon Triple Bond:  Efficient Transformation of Ethynyl Alcohol into Alkene and Carbon Monoxide
  作者：Swarup Datta、Chia-Lung Chang、Kuo-Liang Yeh、Rai-Shung Liu

  DOI：10.1021/ja036246w

  日期：2003.8.1

  We report a new and efficient ruthenium-catalyzed reaction that transforms ethynyl alcohol into alkene and carbon monoxide. The most efficient catalysts are TpRu(PPh3)(CH3CN)2PF6 (10 mol %) and lithium triflate (20 mol %). The mechanism of this reaction was elucidated using an isotope-labeling experiment.

  我们报告了一种新的高效钌催化反应，可将乙炔醇转化为烯烃和一氧化碳。最有效的催化剂是 TpRu(PPh3)(CH3CN)2PF6 (10 mol%) 和三氟甲磺酸锂 (20 mol%)。使用同位素标记实验阐明了该反应的机制。
• US4085272A
  申请人：——

  公开号：US4085272A

  公开（公告）日：1978-04-18
• US4154954A
  申请人：——

  公开号：US4154954A

  公开（公告）日：1979-05-15