4-hydroxy-1-(4-methoxyphenyl)but-2-yn-1-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-hydroxy-1-(4-methoxyphenyl)but-2-yn-1-one
• 英文别名: 4-hydroxy-1-(4-methoxyphenyl)-2-butyn-1-one
• 化学式: C₁₁H₁₀O₃
• 分子量: 190.199
• InChiKey: BFVVMRRQWCJBAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-hydroxy-1-(4-methoxyphenyl)but-2-yn-1-one 在 sodium carbonate 作用下， 以 氘代氯仿 为溶剂， 反应 24.0h， 生成 (E)-4-methoxy-5-(2-(4-methoxyphenyl)-2-oxoethylidene)-2,2-dimethylmorpholin-3-one
  参考文献：
  名称：

  One-Step Assembly of Functionalized Morpholinones and 1,4-Oxazepane-3-ones via [3 + 3]- and [3 + 4]-Annulation of Aza-Oxyallyl Cation and Amphoteric Compounds

  摘要：

  A new [3 + 3]- and [3 + 4]-annulation strategy involving azaoxyallyl cation and [1,m]-amphoteric compounds (m = 3,4) is presented. This concise method enables easy assembly of functionalized saturated N-heterocycles, comprised of six-and seven-membered rings and is of high significance in the context of drug discovery approaches. This reaction also represents a new trapping modality of the azaoxyallyl cation with amphoteric agents of different chain lengths that consist of a heteroatom nucleophilic site and a pi-electrophilic site.

  DOI：

  10.1021/acs.joc.9b02269
• 作为产物：
  描述：

  4-(1-ethoxyethoxy)-1-(4-methoxyphenyl)-2-butyn-1-one 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 生成 4-hydroxy-1-(4-methoxyphenyl)but-2-yn-1-one
  参考文献：
  名称：

  Propiolophenone derivatives

  摘要：

  Propiolophenone衍生物的化学式为##STR1##其中R.sup.6是氢、较低的烷基或化学式##STR2##的基团，以及相应的羟基化合物的化学式##STR3##其中R.sup.6'是氢、较低的烷基、化学式(a)、(b)、(c)、(d)或(e)的基团或化学式--C(R.sup.14)(R.sup.15)OR.sup.16' (f')：表现出保护粘膜和/或抑制胃酸分泌的特性，因此可以用于控制或预防消化道疾病，特别是对抗胃溃疡和/或十二指肠溃疡。

  公开号：

  US04929741A1

文献信息

• Gold‐Catalyzed Bicyclic and [3+2]‐Annulations of Internal Propargyl Alcohols with Nitrones and Imines To Yield to Two Distinct Heterocycles
  作者：Sayaji Arjun More、Tzu‐Hsuan Chao、Mu‐Jeng Cheng、Rai‐Shung Liu

  DOI：10.1002/adsc.202001119

  日期：2021.1.19

  4‐a]indoles from 1‐oxo‐3‐yn‐4‐ols and nitrones is described; this new bicyclic annulation presents the first examples that internal alkynes can react with nitrones to undergo an oxoarylation route. DFT calculations indicate a [3,3]‐sigmatropic shift of initial alkenylgold intermediates to elude the intermediacy of gold carbenes. We also developed new [3+2]‐annulations of the same 1‐oxo‐3‐yn‐4‐ols with imines

  描述了一种由金催化的由1-氧代3-yn-4-醇和硝酮合成的1,3-二氢恶唑并[3,4- a ]吲哚的方法；这种新的双环环化反应是第一个实例，表明内部炔烃可以与硝酮反应进行羰基化反应。DFT计算表明，初始烯基金中间体发生了[3,3]-σ位移，从而避开了金卡宾的中间产物。我们还用亚胺开发了相同的1-oxo-3-yn-4醇与新的[3 + 2]环，有效地生成了oxazolidin-4-yylne衍生物。这些1-oxo-3-ynes的束缚醇可捕获其亚稳的2-azadienium中间体，从而实现新颖的环化反应。我们的机械分析表明，尽管两种产品在结构上相关，但它们是由两个独立的系统生产的。
• Reduced graphene oxide supported copper oxide nanocomposites: An efficient heterogeneous and reusable catalyst for the synthesis of ynones, 1,3‐diynes and 1,5‐benzodiazepines in one‐pot under sustainable reaction conditions
  作者：Rajib Sarkar、Ajay Gupta、Ramen Jamatia、Amarta Kumar Pal

  DOI：10.1002/aoc.5646

  日期：2020.7

  A greener and efficient method for the synthesis of ynones and 1,3‐diynes using copper oxide nanoparticles (CuONPs) doped reduced graphene oxide (CuO@rGO) catalyst under palladium, ligand and solvent free conditions have been developed. The catalyst was subsequently utilized for the synthesis of biologically active 1,5‐benzodiazepines in one pot via sequential addition of acyl chlorides, terminal alkynes

  开发了一种绿色环保，高效的方法，该方法使用钯，配体和无溶剂条件下的氧化铜纳米颗粒（CuONPs）掺杂的还原氧化石墨烯（CuO @ rGO）催化剂合成炔酮和1,3-二炔。该催化剂随后通过依次添加酰氯，末端炔烃和邻苯二胺在一个锅中用于合成具有生物活性的1,5-苯并二氮杂s。该方法最初涉及在乙醇存在下与邻苯二胺反应的原位形成炔酮，以提供多种苯并二氮杂pine。温和的反应条件，良好的产物收率，廉价且可回收的催化剂使该方法在环境方面无害且可持续。
• US4929741A
  申请人：——

  公开号：US4929741A

  公开（公告）日：1990-05-29
• Propiolophenone derivatives
  申请人：Hoffman-La Roche Inc.

  公开号：US04929741A1

  公开（公告）日：1990-05-29

  Propiolophenone derivatives of the formula ##STR1## wherein R.sup.6 is hydrogen, lower alkyl or a group of the formula ##STR2## as well as corresponding hydroxy compounds of the formula ##STR3## wherein R.sup.6' is hydrogen, lower alkyl, a group of formula (a), (b), (c), (d) or (e) or a group of the formula --C(R.sup.14)(R.sup.15)OR.sup.16' (f'): exhibit mucosa-protective and/or gastric acid secretion-inhibiting properties, such that they can be used for the control or prevention of illnesses of the gastrointestinal tract, especially against gastric ulcers and/or duodenal ulcers.

  Propiolophenone衍生物的化学式为##STR1##其中R.sup.6是氢、较低的烷基或化学式##STR2##的基团，以及相应的羟基化合物的化学式##STR3##其中R.sup.6'是氢、较低的烷基、化学式(a)、(b)、(c)、(d)或(e)的基团或化学式--C(R.sup.14)(R.sup.15)OR.sup.16' (f')：表现出保护粘膜和/或抑制胃酸分泌的特性，因此可以用于控制或预防消化道疾病，特别是对抗胃溃疡和/或十二指肠溃疡。
• One-Step Assembly of Functionalized Morpholinones and 1,4-Oxazepane-3-ones via [3 + 3]- and [3 + 4]-Annulation of Aza-Oxyallyl Cation and Amphoteric Compounds
  作者：Tishyasoumya Bera、Bandana Singh、Trevor A. Hamlin、Subash C. Sahoo、Jaideep Saha

  DOI：10.1021/acs.joc.9b02269

  日期：2019.12.6

  A new [3 + 3]- and [3 + 4]-annulation strategy involving azaoxyallyl cation and [1,m]-amphoteric compounds (m = 3,4) is presented. This concise method enables easy assembly of functionalized saturated N-heterocycles, comprised of six-and seven-membered rings and is of high significance in the context of drug discovery approaches. This reaction also represents a new trapping modality of the azaoxyallyl cation with amphoteric agents of different chain lengths that consist of a heteroatom nucleophilic site and a pi-electrophilic site.