4-methylsulfanyl-2-oxo-5,6-diphenyl-2H-pyran-3-carboxylic acid methyl ester | 894790-71-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4-methylsulfanyl-2-oxo-5,6-diphenyl-2H-pyran-3-carboxylic acid methyl ester
• 英文别名: Methyl 4-methylsulfanyl-2-oxo-5,6-diphenylpyran-3-carboxylate
• CAS: 894790-71-7
• 化学式: C₂₀H₁₆O₄S
• 分子量: 352.411
• InChiKey: DWSBPMVBLKGMPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  77.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-methylsulfanyl-2-oxo-5,6-diphenyl-2H-pyran-3-carboxylic acid methyl ester 、 1-苊酮 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 1.5h， 以60%的产率得到methyl 8-(methylsulfanyl)-9,10-diphenylfluoranthene-7-carboxylate
  参考文献：
  名称：

  Synthesis, Electrochemical and Optical Properties of Stable Yellow Fluorescent Fluoranthenes

  摘要：

  A novel series of thermally stable yellow light emitting fluoranthenes with an amine donor and a nitrite acceptor was prepared from a ketene-S,S-acetal under mild conditions without using an organometal catalyst. The organic light emitting device of yellow fluoranthene 10b exhibited substantially low turn-on voltage (2.6 V) and maximum brightness of 470 Cd/m(2) with luminance efficiency of 2.0 Cd/A without using any dopant.

  DOI：

  10.1021/jo100420x
• 作为产物：
  描述：

  二苯基乙酮 、 2-[二(甲硫基)亚甲基]-丙二酸二甲酯 生成 4-methylsulfanyl-2-oxo-5,6-diphenyl-2H-pyran-3-carboxylic acid methyl ester
  参考文献：
  名称：

  使用多米诺序列合成芳基化的高度芳构化茚满

  摘要：

  一种新颖而有效的区域选择性合成方法，用于合成各种芳基化的高度拥挤的7-芳基-5-甲基磺胺林丹-4-甲腈（3a - f），7-芳基-5-甲基磺胺林丹-4-羧酸甲酯（10a – e）和7-芳基-通过6-6-芳基-4-甲基硫烷基-2-氧代-2-氧-2 H-吡喃-3-甲腈（1a - f）和甲基6-芳基-甲基的碱催化反应，制得5-甲基磺酰氨氮-4-羧酸（11a – e）4-甲基硫烷基-2-氧代-2- H-吡喃-3-羧酸酯（9a – e）通过环戊酮（2）已被划定。利用6-芳基-4-秒-氨基-2-氧代-2 H-吡喃-3-甲腈（7a – h），5,6-二芳基-4进一步探索了2-吡喃酮的合成潜力以产生分子多样性。-甲基硫烷基-2-氧代-2 H-吡喃-3-甲腈（5a，b）和5,6-二芳基-4-甲基硫烷基-2-氧代-2- H-吡喃-3-羧酸甲酯（12a，b）环戊酮进行环转化的前驱体，以评估取代基对反应过程的影响，从而获得高度拥挤的茚满，即6

  DOI：

  10.1016/j.tet.2007.07.050

文献信息

• Synthesis of arylated highly congested indans using a domino sequence
  作者：Ramendra Pratap、Brijesh Kumar、Vishnu Ji Ram

  DOI：10.1016/j.tet.2007.07.050

  日期：2007.10

  an-3-carboxylates (9a–e) by cyclopentanone (2) has been delineated. The synthetic potential of 2-pyranone was explored further to generate molecular diversity using 6-aryl-4-sec-amino-2-oxo-2H-pyran-3-carbonitriles (7a–h), 5,6-diaryl-4-methylsulfanyl-2-oxo-2H-pyran-3-carbonitriles (5a,b) and methyl 5,6-diaryl-4-methylsulfanyl-2-oxo-2H-pyran-3-carboxylates (12a,b) as precursors for the ring transformation

  一种新颖而有效的区域选择性合成方法，用于合成各种芳基化的高度拥挤的7-芳基-5-甲基磺胺林丹-4-甲腈（3a - f），7-芳基-5-甲基磺胺林丹-4-羧酸甲酯（10a – e）和7-芳基-通过6-6-芳基-4-甲基硫烷基-2-氧代-2-氧-2 H-吡喃-3-甲腈（1a - f）和甲基6-芳基-甲基的碱催化反应，制得5-甲基磺酰氨氮-4-羧酸（11a – e）4-甲基硫烷基-2-氧代-2- H-吡喃-3-羧酸酯（9a – e）通过环戊酮（2）已被划定。利用6-芳基-4-秒-氨基-2-氧代-2 H-吡喃-3-甲腈（7a – h），5,6-二芳基-4进一步探索了2-吡喃酮的合成潜力以产生分子多样性。-甲基硫烷基-2-氧代-2 H-吡喃-3-甲腈（5a，b）和5,6-二芳基-4-甲基硫烷基-2-氧代-2- H-吡喃-3-羧酸甲酯（12a，b）环戊酮进行环转化的前驱体，以评估取代基对反应过程的影响，从而获得高度拥挤的茚满，即6
• An efficient substituent dependent synthesis of congested pyridines and pyrimidines
  作者：Ramendra Pratap、Brijesh Kumar、Vishnu Ji Ram

  DOI：10.1016/j.tet.2007.07.062

  日期：2007.10

  An efficient and versatile synthesis of various congested pyridines 3a–h, 6a,b, 8a–n, 10a–g, and 16a,b, and (pyrimidin-4-yl)acetonitriles 13a–g has been delineated by base catalyzed ring transformation of suitably functionalized 2H-pyran-2-ones 1a–h, 5, 7, and 15 by formamidine acetate 2a, acetamidine hydrochloride 2b, S-methylisothiourea 9a, pyrazol-1-yl-carboxamidine 9b, and arylamidine hydrochloride

  碱催化的环转化描述了各种拥挤的吡啶3a - h，6a，b，8a - n，10a - g和16a，b以及（嘧啶-4-基）乙腈13a - g的高效通用合成方法。适当官能2 ħ -吡喃-2-酮1A - H ^，5，7，和15由乙酸甲脒2A，乙脒盐酸盐2b中，小号-methylisothiourea图9a，吡唑-1-基甲脒9B，和芳脒盐酸盐12分别在粉末KOH的无水DMF的存在。
• Regioselective synthesis of functionalized naphtho[b]thiophenes through a ‘lactone methodology’
  作者：Manish Dixit、Atul Goel

  DOI：10.1016/j.tetlet.2006.03.081

  日期：2006.5

  Benzo[b]thiophene and its benzannulated derivatives are important classes of compounds due to their unique chemical properties and biosteric relationship with indole. In this letter, we report a convenient route for the synthesis of substituted naphtho[b]thiophenes through a ring transformation reaction of suitably functionalized 2H-pyran-2-ones with 6,7-dihydro-5H-benzothiophene-4-one, in good yields

  苯并[ b ]噻吩及其苯甲环化衍生物由于其独特的化学性质和与吲哚的生物立体关系而成为重要的化合物。在这封信中，我们报告了通过适当官能化的2 H-吡喃-2-酮与6,7-二氢-5 H-苯并噻吩-4-酮的环转化反应，合成取代的萘并[ b ]噻吩的简便方法，收益率很高。
• One-pot regioselective synthesis of dihydronaphthofurans and dibenzofurans
  作者：Manish Dixit、Resmi Raghunandan、Brijesh Kumar、P.R. Maulik、Atul Goel

  DOI：10.1016/j.tet.2006.12.017

  日期：2007.2

  A regioselective approach for the synthesis of substituted naphthofurans and dibenzofurans has been demonstrated through a ring transformation reaction of suitably functionalized 2H-pyran-2-ones by reaction with 6,7-dihydro-5H-benzofuran-4-one and 7-methoxybenzofuran-3-one, respectively, in high yields. The novelty of the procedure lies in the creation of an aromatic ring transformed by 2H-pyran-2-one involving the -COCH2- moiety of a cyclic ketone. (c) 2006 Elsevier Ltd. All rights reserved.
• Synthesis, Electrochemical and Optical Properties of Stable Yellow Fluorescent Fluoranthenes
  作者：Atul Goel、Vijay Kumar、Sumit Chaurasia、Madhu Rawat、Ramesh Prasad、R. S. Anand

  DOI：10.1021/jo100420x

  日期：2010.6.4

  A novel series of thermally stable yellow light emitting fluoranthenes with an amine donor and a nitrite acceptor was prepared from a ketene-S,S-acetal under mild conditions without using an organometal catalyst. The organic light emitting device of yellow fluoranthene 10b exhibited substantially low turn-on voltage (2.6 V) and maximum brightness of 470 Cd/m(2) with luminance efficiency of 2.0 Cd/A without using any dopant.