Benzoylthioessigsaeure-(4-methoxy-phenylamid) | 6502-31-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Benzoylthioessigsaeure-(4-methoxy-phenylamid)
• 英文别名: Benzoylthioessigsaeure-<4-methoxy-anilid>；N-(4-methoxy-phenyl)-3-oxo-3-phenyl-thiopropionamide；N-(4-methoxyphenyl)-3-oxo-3-phenylpropanethioamide
• CAS: 6502-31-4
• 化学式: C₁₆H₁₅NO₂S
• 分子量: 285.367
• InChiKey: UDNFCEOIRZCAKE-UHFFFAOYSA-N

物化性质

• 熔点：
  110-111.5 °C
• 沸点：
  442.3±55.0 °C(Predicted)
• 密度：
  1.239±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  70.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Benzoylthioessigsaeure-(4-methoxy-phenylamid) 在 对甲苯磺酰叠氮 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 [5-(4-methoxy-anilino)-[1,2,3]thiadiazol-4-yl]-phenyl-methanone
  参考文献：
  名称：

  Regitz,M.; Liedhegner,A., Justus Liebigs Annalen der Chemie, 1967, vol. 710, p. 118 - 132

  摘要：

  DOI：
• 作为产物：
  描述：

  2-formyl-N-(4-methoxy-phenyl)-3-oxo-3-phenyl-thiopropionamide 在 盐酸 作用下， 生成 Benzoylthioessigsaeure-(4-methoxy-phenylamid)
  参考文献：
  名称：

  Regitz,M.; Liedhegner,A., Justus Liebigs Annalen der Chemie, 1967, vol. 710, p. 118 - 132

  摘要：

  DOI：

文献信息

• Synthesis of disulfides tethered pyrroles from β-ketothioamides via a bicyclization/ring-opening/oxidative coupling reaction
  作者：Cong-Xiang Li、Rui-Juan Liu、Kun Yin、Li-Rong Wen、Ming Li

  DOI：10.1039/c7ob00655a

  日期：——

  A DABCO-promoted three-component reaction of β-ketothioamides (KTAs), arylglyoxals and 2-cyanoacetates to access disulfides tethered pyrroles by air as oxidant has been disclosed. Importantly, this protocol involves a tandem sequence that includes Knoevenagel condensation, Michael addition, N-cyclization, O-cyclization, ring-opening and oxidative coupling.

  已经公开了DABCO促进的β-酮硫代酰胺（KTA），芳基乙二醛和2-氰基乙酸酯的三组分反应，通过空气作为氧化剂进入二硫键合的吡咯。重要的是，该方案涉及串联序列，该串联序列包括Knoevenagel缩合，Michael加成，N-环化，O-环化，开环和氧化偶联。
• One-pot two-component tandem multiple transformations in the synthesis of N,4-diaryl-2,3-dihydropyrrolo[3,4-c]quinolin-1,3-diones and their 3-thioxo-analogues under neat conditions
  作者：Sreenivas Avula、Satish Koppireddi、Jayaram Reddy Komsani、Jagadeesh Babu Nanubolu、Rambabu Yadla

  DOI：10.1039/c3ra43489c

  日期：——

  An efficient and exclusive synthesis of a decent library of hitherto unknown N,4-diaryl-3-thioxo-2,3-dihydropyrrolo[3,4-c]quinolin-1-ones by a one-pot two-component cascade reaction protocol under solvent-free conditions is disclosed for the first time. This novel procedure involves easy to obtain isatin and N,3-diaryl-3-oxo-propanthioamide derivatives in a series of DMAP catalyzed in situ transformations

  通过一锅双组分级联反应方案高效且独特地合成迄今为止未知的 N,4-diaryl-3-thioxo-2,3-dihydropyrrolo[3,4-c]quinolin-1-ones 库在无溶剂条件下首次公开。这种新颖的方法包括在一系列 DMAP 催化原位转化中容易获得靛红和 N,3-二芳基-3-氧代-丙硫酰胺衍生物，水是唯一的副产物。该协议避免使用昂贵的催化剂、有毒试剂、溶剂和困难的反应条件，并且通过简单地用乙醇洗涤粗反应物质以去除未使用的起始材料，无需柱色谱即可纯化形成的专有产物。这种经济、环保、实用的方法的普遍性是通过准备几个新的2、4-二芳基吡咯并[3,4-c]喹啉-1,3-二酮来自相应的乙烯酮-N,O-缩醛，产率极佳。提出了产物形成的合理反应机制。
• An efficient one-pot protocol for the solvent-free synthesis of novel quinoline-3-thiocarboxamide and 2,3-dihydroquinazolin-4(1H)-one derivatives
  作者：Srikanth Reddy Narra、Sreenivas Avula、Ratnakar Reddy Kuchukulla、Jagadeesh B. Nanubolu、Narsaiah Banda、Rambabu Yadla

  DOI：10.1016/j.tet.2017.06.047

  日期：2017.8

  An efficient and straightforward synthesis of a series of novel poly-substituted quinoline-3-thiocarboxamides 3 and 2-(2-oxo-2-arylethylidene)-2,3-dihydroquinazolin-4(1H)-ones 4 from 3-oxo-N,3-diarylpropanethioamide 1 and the respective 2-aminoarylketone/2-aminoarylcarboxylic acid ester 2 by a two-component solvent-free reaction protocol was described.

  一系列新多取代喹啉-3-硫代甲酰胺的的有效和简单的合成3和2-（2-氧代-2- arylethylidene）-2,3-二氢喹唑啉-4（1 ħ） -酮4从3-氧代-描述了N，3-二芳基丙硫酰胺1和相应的2-氨基芳基酮/ 2-氨基芳基羧酸酯2通过无溶剂的两组分反应方案。
• Acid-promoted rapid solvent-free access to substituted 1,4-dihydropyridines from β-ketothioamides
  作者：Ming Li、Ke-Na Sun、Li-Rong Wen

  DOI：10.1039/c5ra26931h

  日期：——

  β-Ketothioamides (KTAs) have been used as building blocks with aldehydes and β-enaminonitriles for synthesis of 1,4-dihydropyridines in the presence of AcOH under solvent-free conditions within 5 min. This new strategy exhibits remarkable features such as high chemoselectivity, mild reaction conditions, easily available substrates, and good yields.

  β-酮硫酰胺（KTA）已用作醛和β-烯腈的结构单元，用于在无溶剂条件下于5分钟内在AcOH存在下合成1,4-二氢吡啶。这种新策略具有非凡的功能，例如高的化学选择性，温和的反应条件，易于获得的底物和良好的收率。
• Trifluoroborane catalyzed chemoselective synthesis of highly functionalized 1,3‐thiazin‐2‐ylidenes
  作者：Zhibin Luo、Sangepu Bhavanarushi、Avula Sreenivas、Narra Srikanth Reddy、Anil Valeru、Imran Khan、Yin Xu、Bin Liu、Jimin Xie

  DOI：10.1002/jhet.4049

  日期：——

  An efficient chemoselective synthesis of 1,3‐thiazine‐2‐ylidenes was achieved via annulations of β‐aroyl‐thioacetamide with propargyl alcohols using BF3 OEt2 as Lewis acid catalyst. A broad spectrum of substrates was well tolerated under the mild reaction conditions producing desired thiazine heterocyclics in good yields.

  使用BF 3 OEt 2作为路易斯酸催化剂，通过β-芳酰基-硫代乙酰胺与炔丙醇的环化反应，实现了1,3-噻嗪-2-亚基的高效化学选择性合成。在温和的反应条件下，广谱的底物具有良好的耐受性，能够以高收率产生所需的噻嗪杂环。