prop-2-ynyl 3-phenyl-3-oxopropanoate | 83190-30-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: prop-2-ynyl 3-phenyl-3-oxopropanoate
• 英文别名: prop-2-yn-1-yl 3-oxo-3-phenylpropanoate；prop-2-ynyl 3-oxo-3-phenylpropanoate
• CAS: 83190-30-1
• 化学式: C₁₂H₁₀O₃
• 分子量: 202.21
• InChiKey: VMPBTLQAELMBPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  prop-2-ynyl 3-phenyl-3-oxopropanoate 在 三苯基膦氯金 、 三氟甲磺酸 、 水 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 10.0h， 以92%的产率得到3-benzoyl-4-methylfuran-2(5H)-one
  参考文献：
  名称：

  金（I）催化的分子内环状合成4-芳基-2（5H）-呋喃酮

  摘要：

  已开发出一种涉及分子内环化和新型重排的新方法，用于合成4-芳基-2（5 H）-呋喃酮。在氯（三苯基膦）金和三氟甲磺酸的存在下，各种2-2-炔基3-氧代-3-苯基丙酸酯进行环化环化反应，以中等至高收率提供所需的产物。

  DOI：

  10.1002/adsc.201100069
• 作为产物：
  描述：

  苯甲酰乙酸甲酯 、 2-丙炔-1-醇 在 natural kaolinitic clay 作用下， 以 甲苯 为溶剂， 反应 9.0h， 以51%的产率得到prop-2-ynyl 3-phenyl-3-oxopropanoate
  参考文献：
  名称：

  Selective Catalytic Transesterification, Transthiolesterification, and Protection of Carbonyl Compounds over Natural Kaolinitic Clay

  摘要：

  Transesterification and transthiolesterification of beta-keto esters with variety of alcohols and thiols and selective protection of carbonyl functions with various protecting groups catalyzed by natural kaolinitic clay are described. The clay has been found to be an efficient catalyst in transesterifying long chain alcohols, unsaturated alcohols, and phenols to give their corresponding beta-keto esters in high yields. For the first time, transthiolesterification of beta-keto esters with a variety of thiols has been achieved under catalytic conditions. Clay also catalyzes selective transesterification of beta-keto esters by primary alcohols in the presence of secondary and tertiary alcohols giving corresponding beta-keto esters. A systematic study involving the reactivity of different nucleophiles (alcohols, amines, and thiols) toward beta-keto esters is also described. Sterically hindered carbonyl groups as well as alpha,beta-unsaturated carbonyl groups underwent protection without the deconjugation of the double bond. Chemoselective protection of aldehydes in the presence of ketones has also been achieved over natural kaolinitic clay.

  DOI：

  10.1021/jo971404l

文献信息

• Gold‐Catalyzed Cycloisomerization of Sulfur Ylides to Dihydrobenzothiepines
  作者：Christian Knittl‐Frank、Iakovos Saridakis、Thomas Stephens、Rafael Gomes、James Neuhaus、Antonio Misale、Rik Oost、Alberto Oppedisano、Nuno Maulide

  DOI：10.1002/chem.202000622

  日期：2020.8.26

  The metal‐promoted nucleophilic addition of sulfur ylides to π‐systems is a well‐established reactivity. However, the driving force of such transformations, elimination of a sulfide moiety, entails stoichiometric byproducts making them unfavorable in terms of atom economy. In this work, a new take on sulfur ylide chemistry is reported, an atom‐economical gold(I)‐catalyzed synthesis of dihydrobenzo[b]thiepines

  金属促进的硫叶立德与 π 体系的亲核加成是一种成熟的反应性。然而，这种转变的驱动力，即消除硫化物部分，会产生化学计量的副产物，使其在原子经济性方面不利。在这项工作中，报道了硫叶立德化学的新进展，即原子经济的金（I）催化合成二氢苯并[ b ]噻吩。反应在室温下温和条件下进行。
• Site-selective synthesis of 1,3-dioxin-3-ones <i>via</i> a gold(<scp>i</scp>) catalyzed cascade reaction
  作者：Juzeng An、Riccardo Pedrazzani、Magda Monari、Marta Marin-Luna、Carlos Silva Lopez、Marco Bandini

  DOI：10.1039/d0cc02703k

  日期：——

  A novel gold(I)-catalyzed protocol for the synthesis of 4H-1,3-dioxin-3-ones is presented. The protocol exploits a metal induced cascade sequence involving a [3,3]-sigmatropic rearrangement followed by regioselective O-annulation reactions. A wide range of oxygen-based heterocyclic scaffolds (21 examples) were achieved in excellent yield (up to 80%) and a detailed computational investigation as well

  提出了一种新颖的金（I）催化方案，用于合成4 H -1,3-二恶英-3-酮。该协议利用了金属诱导的级联序列，该序列涉及[3,3]-σ重排，然后进行区域选择性的O-环化反应。以优异的收率（高达80％）获得了多种基于氧的杂环支架（多达21个实例），详细的计算研究以及氘标记研究使得所有可能的反应途径都得以绘制，并使反应路线合理化。记录的区域选择性。
• Bismuth(III) Chloride-Catalyzed Highly Efficient Transesterification of β-Keto Esters
  作者：Gowravaram Sabitha、Rangavajjula Srinivas、Peddabuddi Gopal、M. Bhikshapathi、Jhillu Singh Yadav

  DOI：10.1002/hlca.201000113

  日期：2011.1

  Bismuth(III) chloride was found to be an efficient catalyst for the transesterification of a variety of β‐keto esters with a wide range of alcohols to afford transesterified products in good to high yields in short reaction times (see Table).

  发现氯化铋是一种有效的催化剂，可用于多种β-酮酯与多种醇的酯交换反应，从而在较短的反应时间内以高收率获得高收率的酯交换产物（见表）。
• Imidazo[1,2-a]pyridine-based hybrids. Copper-catalyzed cycloaddition synthesis, photophysics, docking, and interaction studies with biomacromolecules
  作者：Eric F. Lopes、Maiara T. Saraiva、Natalí P. Debia、Luana Silva、Otávio A. Chaves、Rafael Stieler、Bernardo A. Iglesias、Fabiano S. Rodembusch、Diogo S. Lüdtke

  DOI：10.1016/j.dyepig.2023.111212

  日期：2023.6

  Herein, we report the connection between imidazo[1,2-a]pyridines with several biologically relevant molecules. The strategy used to build these connections was based on a copper-catalyzed cycloaddition, where different azides and imidazo[1,2-a]pyridine moieties bearing an alkyne were used in this transformation. In total, 8 imidazo[1,2-a]pyridines bearing a terminal alkyne could be synthesized, thus

  在此，我们报告了咪唑并 [1,2 -a ] 吡啶与几种生物学相关分子之间的联系。用于建立这些连接的策略基于铜催化的环加成反应，其中带有炔烃的不同叠氮化物和咪唑并 [1,2 -a ] 吡啶部分用于该转化。总共可以合成 8 个带有末端炔烃的咪唑并 [1,2 -a ] 吡啶，因此可以合成 27 个由三唑环连接的新杂化分子。另外 17 咪唑并[1,2 -a还制备了连接到碳水化合物或天然来源分子的吡啶。基于它们的电子结构，选择了两个基于苯并噻唑部分的例子用于荧光和结合研究。这些化合物在 UV 区域显示吸收最大值，归因于1π-π*电子跃迁。一种化合物中额外羟基的存在允许完全不同的光物理行为，其中可以观察到与 ESIPT 过程相关的双荧光发射。通过 UV-Vis、稳态荧光和分子对接计算进行的光谱研究证明了每种衍生物与 CT-DNA 以及人和牛血清白蛋白（分别为 HSA 和 BSA）建立相互作用的能力。这
• Oxidative Umpolung α-Alkylation of Ketones
  作者：O. Svetlana Shneider、Evgeni Pisarevsky、Peter Fristrup、Alex M. Szpilman

  DOI：10.1021/ol503384c

  日期：2015.1.16

  We disclose a hypervalent iodine mediated α-alkylative umpolung reaction of carbonyl compounds with dialkylzinc as the alkyl source. The reaction is applicable to all common classes of ketones including 1,3-dicarbonyl compounds and regular ketones via their lithium enolates. The α-alkylated carbonyl products are formed in up to 93% yield. An ionic mechanism is inferred based on meticulous analysis, NMR studies, trapping and crossover experiments, and computational studies.