potassium (E)-4-(naphthalen-2-yl)-2-oxobut-3-enoate | 1267589-69-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: potassium (E)-4-(naphthalen-2-yl)-2-oxobut-3-enoate
• 英文别名: potassium (E)-4-(2-naphthyl)-2-oxobut-3-enoate
• CAS: 1267589-69-4
• 化学式: C₁₄H₉O₃*K
• 分子量: 264.322
• InChiKey: KODXFFJNPQJYEY-WVLIHFOGSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.82
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.2
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  potassium (E)-4-(naphthalen-2-yl)-2-oxobut-3-enoate 在 gold(III) chloride 、 C₄₉H₇₆N₄O₄ 、 乙酰氯 、 magnesium triflate 作用下， 以 二氯甲烷 为溶剂， 反应 48.5h， 生成 cyclopentyl 3'-methyl-4'-(naphthalen-2-yl)-3-phenyl-3',4',5',6'-tetrahydrospiro[isochromene-1,2'-pyran]-6'-carboxylate
  参考文献：
  名称：

  β-炔基酮的双金属催化不对称串联反应合成6,6-螺缩酮

  摘要：

  β的对映选择性串联反应，具有β -炔基酮γ不饱和α酮酯是由非手性Au的双金属催化剂体系实现ΙΙΙ盐和手性Ñ，Ñ '二氧化物-镁ΙΙ复杂。随后发生了β-炔基酮的环异构化和不对称分子间[4 + 2]与β，γ-不饱和α-酮酸酯的加成反应，可高效，直接地获得手性多功能6,6-螺缩酮，产率高达97％，94 ％ee和> 19/1 dr此外，基于控制实验的结果，提出了一个催化循环。

  DOI：

  10.1002/anie.201812842
• 作为产物：
  描述：

  丙酮酸 、 2-萘甲醛 在 potassium hydroxide 作用下， 以 甲醇 为溶剂， 以77%的产率得到potassium (E)-4-(naphthalen-2-yl)-2-oxobut-3-enoate
  参考文献：
  名称：

  通过[3 + 3]苯并环化策略轻松 合成取代的二芳基砜†

  摘要：

  已开发出一种由碱介导的[3 + 3]苯环芳构化策略，可将1,3-双（磺酰基）丙烯和β，γ-不饱和α-酮酸酯转化为二芳基砜。该方法可以轻松，无金属且高效地获得高取代的二芳基砜，且收率良好。另外，磺酰基可通过有机锡烷中间体容易地除去或转化为其他官能团。

  DOI：

  10.1039/c8ob00662h

文献信息

• Asymmetric Construction of α-Substituted β-Hydroxy Lactones via Ni Catalyzed Decarboxylative Addition Reaction
  作者：Lingchen He、Ebrahim-Alkhalil M. A. Ahmed、Hongxin Liu、Xingen Hu、Hong-ping Xiao、Juan Li、Jun Jiang

  DOI：10.1021/acs.joc.0c02854

  日期：2021.3.19

  We described a Ni-bidentate oxazoline catalyzed highly enantio- and diastereoselective decarboxylative aldol reaction of 2-oxotetrahydrofuran-3-carboxylic acid/2-oxochromane-3-carboxylic acid derivatives with different kinds of carbonyls. Under optimal reaction conditions, α-substituted β-hydroxy butyrolactones and dihydrocoumarins with an all-carbon quaternary stereocenter have been generated with

  我们描述了Ni-双齿恶唑啉催化的2-氧代四氢呋喃-3-羧酸/ 2-氧代苯并-3-羧酸衍生物与不同种类的羰基的高度对映体和非对映体选择性脱羧羟醛反应。在最佳反应条件下，已生成具有全官能团四价立体中心的α-取代的β-羟基丁内酯和二氢香豆素。此外，还描述了产物的充分转化，其中通过氢化和开环反应分别顺利地构建了脂肪族叔醇和多取代的1,4-二醇。
• Synthesis of Chiral Bispirotetrahydrofuran Oxindoles by Cooperative Bimetallic-Catalyzed Asymmetric Cascade Reaction
  作者：Meng-Meng Liu、Xiao-Chao Yang、Yuan-Zhao Hua、Jun-Biao Chang、Min-Can Wang

  DOI：10.1021/acs.orglett.9b00386

  日期：2019.4.5

  Under mild conditions, a broad range of bispirotetrahydrofuran oxindoles have been synthesized with excellent stereoselectivities through the cascade Michael/hemiketalization/Friedel–Crafts reaction of β,γ-unsaturated α-ketoamide and 2-hydroxy-1-indanone. The reaction can be performed on a gram scale with low catalyst loading (2 mol %) without impacting its efficiency.

  通过协同双核锌-AzePhenol催化剂描述了一种对映选择性构建双螺四氢呋喃羟吲哚的新的有效途径。在温和的条件下，通过β，γ-不饱和α-酮酰胺和2-羟基-1-茚满酮的级联迈克尔/半缩酮化/弗里德-克拉夫茨反应，合成了多种具有优良立体选择性的双螺四氢呋喃恶吲哚。该反应可以以克级进行，催化剂负载量低（2mol％），而不会影响其效率。
• Organocatalytic Functionalization of Carboxylic Acids: Isothiourea-Catalyzed Asymmetric Intra- and Intermolecular Michael Addition−Lactonizations
  作者：Dorine Belmessieri、Louis C. Morrill、Carmen Simal、Alexandra M. Z. Slawin、Andrew D. Smith

  DOI：10.1021/ja109975c

  日期：2011.3.2

  Tetramisole promotes the catalytic asymmetric intramolecular Michael addition-lactonization of a variety of enone acids, giving carbo- and heterocyclic products with high diastereo- and enantiocontrol (up to 99:1 dr, up to 99% ee) that are readily derivatized to afford functionalized indene and dihydrobenzofuran carboxylates. Chiral isothioureas also promote the catalytic asymmetric intermolecular Michael addition-lactonization of arylacetic acids and alpha-keto-beta,gamma,-unsaturated esters, giving anti-dihydropyranones with high diastereo- and enantiocontrol (up to 98:2 dr, up to 99% ee).
• Enantioselective NHC-catalysed redox [4+2]-hetero-Diels-Alder reactions using α-aroyloxyaldehydes and unsaturated ketoesters
  作者：James E. Taylor、Alyn T. Davies、James J. Douglas、Gwydion Churchill、Andrew D. Smith

  DOI：10.1016/j.tetasy.2017.01.002

  日期：2017.2

  N-Heterocyclic carbene (NHC)-catalysed redox [4+2]-hetero-Diels-Alder reactions of alpha-aroyloxyaldehydes with either beta,gamma-unsaturated alpha-ketoesters or alpha,beta-unsaturated gamma-ketoesters generates substituted syn-dihydropyranones in good yield with excellent enantioselectivity (up to >99:1 er). The product diastereoselectivity is markedly dependent upon the nature of the unsaturated enone substituent. The presence of either electron-neutral or electron-rich aryl substituents gives excellent diastereoselectivity (up to >99:5 dr), while electron-deficient aryl substituents give reduced diastereoselectivity. In these cases, the syn-dihydropyranone products are more susceptible to base-promoted epimerisation at the C(4)-position under the reaction conditions, accounting for the lower diastereoselectivity obtained. (C) 2017 Published by Elsevier Ltd.