2-(bis(methylthio)methylene)-N-(4-chlorophenyl)-3-oxobutanamide | 146140-56-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(bis(methylthio)methylene)-N-(4-chlorophenyl)-3-oxobutanamide
• 英文别名: 2-[bis(methylsulfanyl)methylidene]-N-(4-chlorophenyl)-3-oxobutanamide
• CAS: 146140-56-9
• 化学式: C₁₃H₁₄ClNO₂S₂
• 分子量: 315.845
• InChiKey: BDVNZDFPLDKJRE-UHFFFAOYSA-N

物化性质

• 熔点：
  154-156 °C
• 沸点：
  503.0±50.0 °C(Predicted)
• 密度：
  1.342±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  96.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(bis(methylthio)methylene)-N-(4-chlorophenyl)-3-oxobutanamide 在 一水合肼 作用下， 以 水 为溶剂， 反应 3.8h， 以94%的产率得到C₁₂H₁₂ClN₃OS
  参考文献：
  名称：

  Water Mediated Construction of Trisubstituted Pyrazoles/Isoxazoles Library Using Ketene Dithioacetals

  摘要：

  A small molecule library of alkyl, sulfone, and carboxamide functionalized pyrazoles and isoxazoles has been developed via a rapid sequential condensation of various alpha-acylketene dithioacetals (1a-o) with hydrazine hydrate or hydroxylamine hydrochloride, followed by oxidation of sulfide to sulfone using water as the reaction medium. An efficient and safe oxidation of sulfides (4/5a-o) to the corresponding sulfones (6/7a-o) using sodium per borate system in aqueous medium is reported. The concise and two step synthesis of trisubstituted pyrazoles and isoxazoles was investigated under variety of reaction condition. The newly developed methodology has the advantage of excellent yield and chemical purity with short reaction time using water as a solvent.

  DOI：

  10.1021/cc900148q
• 作为产物：
  描述：

  二硫化碳 、 溴甲烷 、 乙酰基乙酰对氯苯胺 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以100%的产率得到2-(bis(methylthio)methylene)-N-(4-chlorophenyl)-3-oxobutanamide
  参考文献：
  名称：

  [5 + 1] Annulation:  A Synthetic Strategy for Highly Substituted Phenols and Cyclohexenones

  摘要：

  A novel [5 + 1] annulation strategy is developed for the synthesis of highly substituted phenols and cyclohexenones from alpha-alkenoyl ketenedithioacetals and nitroalkanes.

  DOI：

  10.1021/ja043023c

文献信息

• Thermal Cyclization of Ketene Dithioacetals: A Convenient Synthetic Route to Substituted 2(1<i>H</i>)-Quinolinones and 2(1<i>H</i>)-Pyridones
  作者：Chwang Siek Pak、Eun Bok Choi

  DOI：10.1055/s-1992-26361

  日期：——

  Acyl(arylcarbamoyl)ketene dithioacetals 2 and acyl(1-alkenylcarbamoyl)ketene dithioacetals 5 obtained from the corresponding ß-oxo amides 1, 4 were thermally cyclized to give various 3-acyl-4-alkylthio-2(1H)-quinolinones 3, and 3-acyl-4-alkylthio-5-aryl-2(1H)-pyridones 6, respectively, depending on the substituent of the amide group.

  由相应的β-氧代酰胺1、4获得的酰基（芳基氨基甲酰基）烯酮二硫代缩醛2和酰基（1-烯基氨基甲酰基）烯酮二硫代缩醛5，根据酰胺基团的取代情况，经热环化反应分别生成多种3-酰基-4-烷硫基-2(1H)喹啉酮3和3-酰基-4-烷硫基-5-芳基-2(1H)吡啶酮6。
• Synthesis of β-Lactam from Acyl(Arylcarbamoyl)-<i>S,S</i>-bis(alkylketene) Dithioacetal: Revised Structure of the Product from Thermal Cyclization of Acyl(Arylcarbamoyl)-<i>S,S</i>-bis(alkylketene) Dithioacetal
  作者：Chwang Siek Pak、Eun Bok Choi、Guy Hwan Yon、Hyeon Kyu Lee、Hee Cheol Yang、Chung Youl Yoo

  DOI：10.1055/s-2003-42466

  日期：——

  The structure of the quinolinone obtained from thermal cyclization of ketene dithioacetal has been revised by X-ray crystallographic analysis as 4-quinolinone instead of the previously reported 2-quinolinone. In the course of study on the mechanistic feature of the thermal cyclization, highly substituted β-lactams were obtained by alkylating β-lactam anion with MEMCl, MOMCl, or MeI in the presence of NaH.

  通过X射线晶体学分析，从酮烯二硫缩醛热环化得到的喹诺酮结构已修正为4-喹诺酮，而非先前报道的2-喹诺酮。在进行热环化机理特征的研究过程中，通过使用MEMCl、MOMCl或MeI在NaH存在下对β-内酰胺阴离子进行烷基化，获得了高度取代的β-内酰胺。
• A Concise [3 + 3] Heteroaromatization Synthetic Strategy Afford Dicarboxamide Functionalized Novel Pyrazolo[1,5-<i>a</i>]Pyrimidines
  作者：Anilkumar S. Patel、Naval P. Kapuriya、Yogesh T. Naliapara

  DOI：10.1002/jhet.2860

  日期：2017.9

  A concise and effective approach to dicarboxamide functionalized novel pyrazolo[1,5‐a]pyrimidine has been developed. The method involves [3 + 3] hetroaromatization of oxoketene dithioacetals (16a–x) with 5‐amino‐N‐cyclohexyl‐3‐(methylthio)‐1H‐pyrazole‐4‐carboxamide (12) in the presence of K2CO3. This method has advantages of excellent yields, operational simplicity, and avoidance of hazardous base

  已经开发出一种简洁有效的方法将二甲酰胺官能化的新型吡唑并[1,5- a ]嘧啶。该方法涉及在存在K 2 CO的情况下，用5-氨基-N-环己基-3-（甲硫基）-1H-吡唑-4-羧酰胺[ 12 +3]氧化氧杂环丁二硫缩醛（16a–x）的芳香化。3。该方法的优点是产率高，操作简单并且避免了诸如哌啶的有害碱。
• Facile synthesis of highly functionalized novel pyrazolopyridones using oxoketene dithioacetal and their anti-HIV activity
  作者：Mahesh M. Savant、Kartik D. Ladva、Archna B. Pandit

  DOI：10.1080/00397911.2018.1458239

  日期：2018.7.3

  synthesized starting from various oxoketene dithioacetals. The cyclocondensation reaction of 2-(bis(methylthio)methylene)-3-oxo-N-arylbutanamide 2a–w with cyanoacetamide using NaOiPr as base under reflux condition afforded novel highly functionalized pyridone 3a–w derivatives. Further, [3 + 2] cyclocondensation reaction of pyridones with hydrazine in the presence of alcohol was yielded pyrazolopyridones

  摘要 以各种氧代烯酮二硫缩醛为原料合成了一系列新型 3-amino-4,5-dihydro-6-methyl-4-oxo-N-aryl-1H-pyrazolo[4,3-c]pyridine-7-carboxamide。 . 2-(双(甲硫基)亚甲基)-3-氧代-N-芳基丁酰胺2a-w与氰基乙酰胺在回流条件下使用NaOiPr作为碱的环缩合反应提供了新型的高度官能化的吡啶酮3a-w衍生物。此外，在醇的存在下，吡啶酮与肼的 [3 + 2] 环缩合反应以优异的产率得到吡唑并吡啶酮（23 个）4a-w。使用 MTT 方法评估所有新合成的化合物的体外抗 HIV 活性。大多数这些化合物对 HIV-1 (IIIB) 和 HIV-2 (ROD) 毒株显示出中等至强效活性，IC50 范围从 >18 IC50[μg/ml] 到 <100 IC50[μg/ml]。他们之中，化合物 4j 和 4v 被确定为两种类型的
• PBr₃-mediated [5 + 1] annulation of α-alkenoyl-α-carbamoyl ketene-S,S-acetals: access to substituted pyridine-2,6(1H,3H)-diones
  作者：Liping Shi、Qian Zhang、Fengjiao Gan、Rui Zhang、Yuanli Ding、Chun Liu、Dewen Dong

  DOI：10.1039/c5ra13498f

  日期：——

  A facile and efficient synthesis of substituted pyridine-2,6(1H,3H)-diones via an intramolecular [5 + 1] annulation of readily available α-alkenoyl-α-carbamoyl ketene-S,S-acetals mediated by phosphorus bromide (PBr3) under very mild conditions is described.

  一种简便的和取代的吡啶-2,6-（1高效合成ħ，3 ħ） -二酮通过分子内[5 + 1]容易获得的环α链烯酰基-α -氨基甲酰基二硫缩烯酮小号，小号-acetals由磷介导的描述了在非常温和的条件下使用溴化物（PBr 3）。