6-isopropyl-4-methylsulfanyl-2-oxo-2H-pyran-3-carbonitrile | 916065-57-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 6-isopropyl-4-methylsulfanyl-2-oxo-2H-pyran-3-carbonitrile
• 英文别名: 6-isopropyl-4-(methylthio)-2-oxo-2H-pyran-3-carbonitrile；4-methylsulfanyl-2-oxo-6-propan-2-ylpyran-3-carbonitrile
• CAS: 916065-57-1
• 化学式: C₁₀H₁₁NO₂S
• 分子量: 209.269
• InChiKey: ALPNKAWRCQXZKH-UHFFFAOYSA-N

物化性质

• 沸点：
  287.2±40.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  75.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  哌啶 、 6-isopropyl-4-methylsulfanyl-2-oxo-2H-pyran-3-carbonitrile 以 甲醇 为溶剂， 反应 8.0h， 生成 2-Oxo-4-piperidin-1-yl-6-propan-2-ylpyran-3-carbonitrile
  参考文献：
  名称：

  的合成Ó，米通过负碳离子引发的环转型策略-cymene-芯的联芳基

  摘要：

  源自两个或多个“异戊二烯单元”的芳族化合物是在几种具有生物学重要性的天然产物中发现的核心结构。在它们之中，由于与它们相关的独特的结构和生物学特性，因此受到特别的关注。在这封信中，我们描述了一种快速合成的以芳烃诱导的2 H-吡喃-2-酮与酮的环化反应，以供体和受体取代基官能化制备的以供体和受体取代基为功能的苯并二甲基核不对称联芳基的合成方法。

  DOI：

  10.1016/j.tetlet.2006.08.105
• 作为产物：
  描述：

  3-甲基-2-丁酮 、 2-氰-3,3-二(甲硫基)丙烯酸甲酯 在 氢氧化钾 作用下， 以 二甲基亚砜 为溶剂， 以60%的产率得到6-isopropyl-4-methylsulfanyl-2-oxo-2H-pyran-3-carbonitrile
  参考文献：
  名称：

  的合成Ó，米通过负碳离子引发的环转型策略-cymene-芯的联芳基

  摘要：

  源自两个或多个“异戊二烯单元”的芳族化合物是在几种具有生物学重要性的天然产物中发现的核心结构。在它们之中，由于与它们相关的独特的结构和生物学特性，因此受到特别的关注。在这封信中，我们描述了一种快速合成的以芳烃诱导的2 H-吡喃-2-酮与酮的环化反应，以供体和受体取代基官能化制备的以供体和受体取代基为功能的苯并二甲基核不对称联芳基的合成方法。

  DOI：

  10.1016/j.tetlet.2006.08.105

文献信息

• Regioselective Synthesis of Functionally Crowded Benzenes at Room Temperature through Ring Transformation of 2<i>H</i>-Pyran-2-ones
  作者：Atul Goel、Fateh Singh、Vijay Kumar

  DOI：10.1055/s-2007-984885

  日期：——

  An expeditious synthesis of highly substituted benzenes with electron-withdrawing or electron-donating substituents is ­described and illustrated by carbanion-induced ring transformation of 2H-pyran-2-one with malononitrile in excellent yield. The ­novelty of the reaction lies in the creation of an aromatic ring at room temperature from a six-membered lactone under mild reaction conditions.

  高效合成具有吸电子或给电子取代基的高度取代苯的方法被描述和展示，该方法通过2H-吡喃-2-酮与丙二腈在优异产率下的碳负离子诱导环转化实现。反应的新颖之处在于在温和反应条件下，从六元内酯在室温下创造出一个芳香环。
• Regioselective synthesis of 2-amino-isophthalonitriles through a ring transformation strategy
  作者：Fateh V. Singh、Vijay Kumar、Brijesh Kumar、Atul Goel

  DOI：10.1016/j.tet.2007.08.056

  日期：2007.11

  An expeditious synthesis of several 2-amino-isophthalonitriles and their biaryl compounds is described and illustrated by carbanion-induced ring transformation of functionalized 2H-pyran-2-ones with malononitrile in excellent yields. The strength of the reaction lies in the creation of an aromatic ring at room temperature from six-membered lactones under mild reaction conditions. This approach is an

  描述了几种2-氨基-间苯二甲腈及其联芳基化合物的快速合成方法，并通过羰基诱导的官能化的2 H-吡喃-2-酮与丙二腈的极高收率进行了环转化。反应的强度在于在室温下由六元内酯在温和的反应条件下产生芳环。该方法是2 H-吡喃-2-酮与亲二烯物的Diels-Alder反应的替代方法，后者需要强制加热条件才能获得苯衍生物。
• Synthesis of Solution-Processable Donor–Acceptor Pyranone Dyads for White Organic Light-Emitting Devices
  作者：Chandra P. Sharma、Neeraj M. Gupta、Jagriti Singh、Rohit Ashok Kumar Yadav、Deepak Kumar Dubey、Kundan S. Rawat、Ajay K. Jha、Jwo-Huei Jou、Atul Goel

  DOI：10.1021/acs.joc.9b00293

  日期：2019.6.21

  A series of donor-acceptor pyranones (3a-m, 4a-h) were synthesized using alpha-oxo-ketene-S,S-acetal as the synthon for their application as emissive materials for energy-saving organic light-emitting devices (OLEDs). Among them, five pyranones 3f, 3g, 3h, 3m, and 4e exhibited highly bright fluorescence in the solid state and weak or no emission in the solution state. Photophysical analysis of these dyes revealed that only 3f and 3m showed aggregation-induced emission behavior in a THF/water mixture (0-99%) with varying water fractions (f(w)) leading to bright fluorescence covering the entire visible region, while other derivatives 3g, 3h, and 4e did not show any fluorescence signal. The computational studies of the compounds revealed that the longer wavelength absorption originates from HOMO to LUMO electronic excitation. These dyes exhibited good thermal stability with 5% weight loss temperature in the range of 218-347 degrees C. The potential application of the donor-acceptor pyranone dyads was demonstrated by fabrication of solution-processed OLEDs. Remarkably, OLED devices prepared using highly emissive compounds 6-(anthracen-9-yl)-4-(methylthio)-2-oxo-2H-pyran-3-carbonitrile (3m) and 6-(4-methoxyphenyl)-4-(methylthio)-2-oxo-2H-pyran-3-carbonitrile (3f) displayed pure white emission with CIE coordinates of (0.29, 0.31) and (0.32, 0.32), respectively. Additionally, the resultant devices exhibited external quantum efficiencies of 1.9 and 1.2% at 100 cd m(-2), respectively.
• New Fluoranthene FLUN-550 as a Fluorescent Probe for Selective Staining and Quantification of Intracellular Lipid Droplets
  作者：Atul Goel、Ashutosh Sharma、Manoj Kathuria、Arindam Bhattacharjee、Ashwni Verma、Prabhat R. Mishra、Aamir Nazir、Kalyan Mitra

  DOI：10.1021/ol403470d

  日期：2014.2.7

  A new class of live cell permeant, nontoxic fluoranthene-based fluorescent probe (FLUN-550) having a high Stokes shift in aqueous medium has been discovered. It showed selective staining of lipid droplets (LDs, dynamic cytoplasmic organelles) at a low concentration without background noise in in vitro live cell imaging of 3T3-L1 preadipocytes, J774 macrophages, MCF7 breast cancer cells, and single-celled, parasitic protozoa Leishmania donovani promastigotes and in vivo nonparasitic soil nematode C. elegans.