5-[1-Hydroxy-2-(4-methoxy-phenyl)-ethylidene]-2,2-dimethyl-[1,3]dioxane-4,6-dione | 153525-08-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-[1-Hydroxy-2-(4-methoxy-phenyl)-ethylidene]-2,2-dimethyl-[1,3]dioxane-4,6-dione
• 英文别名: 5-[1-Hydroxy-2-(4-methoxyphenyl)ethylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione
• CAS: 153525-08-7
• 化学式: C₁₅H₁₆O₆
• 分子量: 292.288
• InChiKey: YKAAYLBGQHEMIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-[1-Hydroxy-2-(4-methoxy-phenyl)-ethylidene]-2,2-dimethyl-[1,3]dioxane-4,6-dione 在 (R)-BINAP-Ru(II) 氢氧化钾 、 氢气 、 三苯基膦 作用下， 以 乙醇 、 氯仿 为溶剂， 80.0 ℃ 、11.15 MPa 条件下， 反应 27.0h， 生成 (R)-3-Hydroxy-4-(4-methoxy-phenyl)-thiobutyric acid S-pyridin-2-yl ester
  参考文献：
  名称：

  A protocol for the efficient synthesis of enantiopure .beta.-substituted .beta.-lactones

  摘要：

  DOI：

  10.1021/jo00079a049
• 作为产物：
  描述：

  丙二酸环(亚)异丙酯 、 4-甲氧基苯乙酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 3.75h， 生成 5-[1-Hydroxy-2-(4-methoxy-phenyl)-ethylidene]-2,2-dimethyl-[1,3]dioxane-4,6-dione
  参考文献：
  名称：

  对映选择性碳级联反应：环戊二烯的有效方法及其在Diels-Alder反应中的应用

  摘要：

  提出了一种不对称卡宾级联反应，该反应通过卡宾/炔烃复分解和形式（3 + 2）环加成反应进行，并将炔基连接的烯醇重氮乙酸酯转化为手性双环环戊二烯。并且迄今尚未公开这些卡宾级联转化的催化不对称形式。在机理研究中观察到了环丙烯中间体的质子信号，清楚地表明了反应途径。此外，这些产物通过Diels-Alder反应被拦截，从而以高收率和对映选择性提供桥连的多环结构。

  DOI：

  10.1002/adsc.201501106

文献信息

• Acylation of Meldrum’s acid with arylacetic acid imidazolides as a convenient method for the synthesis of 4-aryl-3-oxobutanoates
  作者：A. A. Shimkin、V. Z. Shirinian、A. K. Mailian、D. V. Lonshakov、V. V. Gorokhov、M. M. Krayushkin

  DOI：10.1007/s11172-011-0019-9

  日期：2011.1

  C-Acylation of Meldrum’s acid by (het)arylacetic acids in ethanol in the presence of 1,1′-carbonyldiimidazole leads to ethyl 4-(het)aryl-3-oxobutanoates in high yields.

  在 1,1′-羰基二咪唑存在下，(庚)芳基乙酸在乙醇中对 Meldrum's 酸进行 C-酰化，可高产 4-(庚)芳基-3-氧代丁酸乙酯。
• Solid Phase Synthesis of 3-Acyltetramic Acids
  作者：Lutz Weber、Patrick Iaiza、Gérard Biringer、Pierre Barbier

  DOI：10.1055/s-1998-1862

  日期：1998.10

  We report a solid-phase synthesis of 3-acyltetramic acids that are components of naturally occurring antibiotics. The products were obtained in satisfactory purity by a novel cyclization-cleavage strategy via a Dieckmann condensation.

  我们报告了 3-酰基四酸的固相合成，3-酰基四酸是天然抗生素的成分。通过迪克曼缩合的新型环化-裂解策略获得了令人满意的纯度的产物。
• Bioisosteric replacement of an acylureido moiety attached to an indolin-2-one scaffold with a malonamido or a 2/4-pyridinoylamido moiety produces a selectively potent Aurora-B inhibitor
  作者：Hsiao-Chun Wang、Ajit Dhananjay Jagtap、Pei-Teh Chang、Jia-Rong Liu、Chih-Peng Liu、Hsiang-Wen Tseng、Grace Shiahuy Chen、Ji-Wang Chern

  DOI：10.1016/j.ejmech.2014.07.033

  日期：2014.9

  Bioisosteric replacement of acylureido moiety in 6-acylureido-3-pyrrolylmethylidene-2-oxoindoline derivatives resulted in a series of malonamido derivatives with indolin-2-one scaffold (11-14). Further conformational restrictions of the malonamido moiety led to 2-oxo-1,2-dihydropyridine (21-25) or a 4-oxo-1,4-dihydropyridine derivatives (31-36). 4-Oxo-1,4-dihydropyridine derivatives were more potent Aurora B inhibitors than their 2-oxo-1,2-dihydropyridine counterparts and demonstrated cytotoxicities against A549 and HepG2 cells in the submicromolar range. In A549 cells, 31h decreased phosphorylation of histone H3, triggered polyploidy, induced expression of pro-apoptotic Fas and FasL with subsequent activation of caspase 8, resulting into apoptosis. In a Huh7-xenograft mouse model, 31h demonstrated potent in vivo efficacy with a daily dose of 5 mg/kg.
• A Pyrazole to Furan Rearrangement. Thermolysis of 5-Azido-4-formylpyrazoles
  作者：Niels Svenstrup、Klaus B. Simonsen、Niels Thorup、Jørgen Brodersen、Wim Dehaen、Jan Becher

  DOI：10.1021/jo9822075

  日期：1999.4.1

  5-Azido-3-benzyl-4-formyl-1-phenylpyrazoles 1a-c extrude dinitrogen upon heating in toluene to give the corresponding nitrenes, which immediately rearrange via a new ring-opening ring-closure reaction to produce an equimolar mixture of 4-cyano-2-phenyl-3-phenylazofurans 2a-c and 3-benzyl-4-cyano-1-phenylpyrazoles 3a-c. The formation of the 4-cyano-2-phenyl-3-phenylazofurans 2a-c is the first example in the pyrazole series of a nitrene rearrangement, in which the parent heterocyclic system of the product differs from that of the starting material. The isolation of equimolar amounts of the two products points to the fact that their formation occurs by two mechanistically interconnected pathways, between which the exchange of a redox equivalent takes place. Evidence for the existence of two mechanistically interlinked pathways is presented, and the insight into the stoechiometry of the reaction is taken advantage of to optimize the reaction with respect to either of the two products 2 or 3. Thus, it is demonstrated how one can bias the two pathways using external reagents, thereby changing the product distribution ratio 2:3 from 1:1 in the unbiased case, to 1:4 in one direction, and to better than 20:1 in the other direction.
• Enantioselective Carbene Cascade: An Effective Approach to Cyclopentadienes and Applications in Diels-Alder Reactions
  作者：Xiangbo Wang、Yunfei Zhou、Lihua Qiu、Ruwei Yao、Yang Zheng、Cheng Zhang、Xiaoguang Bao、Xinfang Xu

  DOI：10.1002/adsc.201501106

  日期：2016.5.19

  An asymmetric carbene cascade reaction, which proceeds through carbene/alkyne metathesis and formal (3+2) cycloaddition and converts alkynyl‐tethered enol diazoacetates to chiral bicyclic cyclopentadienes, is presented; and no catalytic asymmetric version of these carbene cascade transformations has been disclosed so far. The proton signals of the cyclopropene intermediates are observed in the mechanism

  提出了一种不对称卡宾级联反应，该反应通过卡宾/炔烃复分解和形式（3 + 2）环加成反应进行，并将炔基连接的烯醇重氮乙酸酯转化为手性双环环戊二烯。并且迄今尚未公开这些卡宾级联转化的催化不对称形式。在机理研究中观察到了环丙烯中间体的质子信号，清楚地表明了反应途径。此外，这些产物通过Diels-Alder反应被拦截，从而以高收率和对映选择性提供桥连的多环结构。