5-cyano-2,2-dimethyl-6-phenylamino-2,3-dihydro-1,3-thiazin-4(1H)-one | 884536-76-9

• 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: 5-cyano-2,2-dimethyl-6-phenylamino-2,3-dihydro-1,3-thiazin-4(1H)-one
• 英文别名: 3,4-dihydro-2,2-dimethyl-4-oxo-6-(phenylamino)-2H-1,3-thiazine-5-carbonitrile；6-anilino-2,2-dimethyl-4-oxo-3H-1,3-thiazine-5-carbonitrile
• CAS: 884536-76-9
• 化学式: C₁₃H₁₃N₃OS
• 分子量: 259.332
• InChiKey: MORDXXMJCSJPQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  90.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-cyano-2,2-dimethyl-6-phenylamino-2,3-dihydro-1,3-thiazin-4(1H)-one 在 对甲苯磺酸 、 三乙胺 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 6.0h， 生成 2,2-dimethyl-7-(2,2-dimethylpropanoyl)-5-phenylamino-2,3-dihydrothieno[3,4-d]pyrimidin-4(1H)-one
  参考文献：
  名称：

  功能化的 2,3-二氢噻吩并[2,3-d]嘧啶-4(1H)-酮的合成及其再环化为2,3-二氢噻吩并[3,4-d]嘧啶-4(1H)-酮

  摘要：

  通过 6-芳基(烷基)氨基-5-氰基-2,3-二氢-1,3-噻嗪-4(10)-酮与α-卤代酮在三乙胺、2,3-二氢噻吩[已经合成了 2,3-d]pyrimidin-4(1H)-ones，并发现并研究了它们在酸催化下再循环生成 2,3-dihydrothieno[3,4-d]pyrimidin-4(1H)-ones。© 2006 Wiley Periodicals, Inc. 杂原子化学 17:104–111, 2006; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20181

  DOI：

  10.1002/hc.20181
• 作为产物：
  描述：

  硫代异氰酸苯酯 在 溶剂黄146 、 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.62h， 生成 5-cyano-2,2-dimethyl-6-phenylamino-2,3-dihydro-1,3-thiazin-4(1H)-one
  参考文献：
  名称：

  Tandem One-pot Synthesis of Polysubstituted 1,3-Thiazine Derivatives

  摘要：

  AbstractA tandem one‐pot synthesis of polysubstituted 1,3‐thiazines has been developed by reacting with cyanoacetamide and isothiocyanate derivatives to give rise to 2‐cyano‐3‐mercaptoacrylamides, which are trapped in situ by various aldehydes or diversely substituted ketones through intermolecular cyclization, providing polysubstituted 1,3‐thiazine derivatives in short reaction times with good to excellent yields. The salient features of this novel protocol are operational simplicity, accessing the desired products from the readily available starting materials and easy of product isolation and may find wide spread applications in medicinal chemistry.

  DOI：

  10.1002/cjoc.201100067

文献信息

• A Rich Array of Reactions of Cyanomonothiocarbonylmalonamides RNHCSCH(CN)CONHR‘ and Their Thioenols RNHC(SH)C(CN)CONHR‘¹
  作者：Ahmad Basheer、Zvi Rappoport

  DOI：10.1021/jo7022262

  日期：2008.2.1

  The thioenols derived from cyanomonothiocarbonylmalonamides and a cyanodithiocarbonylmalonamide were found to be very reactive species. They react under a variety of conditions such as crystallization, reaction with several carbonyl compounds, and reactions with another thioenol molecule to give a variety of products, mostly heterocycles, including substituted 2,3-dihydroisothiazole-3-ones and 3-thione

  发现衍生自氰基单硫代羰基丙二酰胺和氰基二硫代羰基丙二酰胺的硫醇是非常活泼的物质。它们在各种条件下反应，例如结晶，与几种羰基化合物反应以及与另一个硫烯醇分子反应，从而产生各种产物，主要是杂环化合物，包括取代的2,3-二氢异噻唑-3-酮和3-硫酮2 -取代的亚甲基噻唑，3,4-二氢-1,3-噻嗪-4-酮和4-硫酮，二乙烯基硫醚，1,2-二硫杂环戊烷基和3,7-二氮杂[3.3.0]双环辛烷衍生物。这些反应建议的机制包括自由基机制，亲核取代和缩合。
• Synthesis of 2,3-dihydro-1,3-thiazin-4(1H)- ones and their remarkably facile recyclization to 2,3-dihydropyrimidin-4(1H)-ones
  作者：Mykhaylo V. Vovk、Volodymyr A. Sukach、Alexander N. Chernega、Volodymyr V. Pyrozhenko、Andriy V. Bol'but,、Alexander M. Pinchuk

  DOI：10.1002/hc.20129

  日期：——

  1-alkyl- (aryl)-5-cyano-6-mercapto-2,3-dihydropyrimidin- 4(1H)-ones. Alkylation of the latter with dimethyl sulfate in situ furnishes 1-alkyl(aryl)-6-alkylthio-5- cyano-2,3-dihydropyrimidin-4(1H)-ones, whereas boiling them in ethanol with an excess of hydrochloric acid leads to starting 2,3-dihydro-1,3-thiazin-4(1H)-ones. © 2005 Wiley Periodicals, Inc. Heteroatom Chem 16:426–436, 2005; Published online in

  功能化的 2,3-二氢-1,3-thiazin-4(1H)-one 衍生物已通过 3-烷基（芳基）氨基-2-氰基-3-巯基丙烯酰胺与醛和酮在酸性催化下的环缩合反应合成。6-烷基(芳基)氨基-5-氰基-2,3-二氢-1,3-噻嗪-4(1H)-酮，当用氢氧化钾的稀溶液处理时，转化为异构化合物，1-烷基-(芳基)-5-氰基-6-巯基-2,3-二氢嘧啶-4(1H)-ones。后者用硫酸二甲酯在原位烷基化得到 1-烷基（芳基）-6-烷硫基-5-氰基-2,3-二氢嘧啶-4（1H）-酮，而在乙醇中用过量的盐酸煮沸会导致到起始 2,3-dihydro-1,3-thiazin-4(1H)-ones。© 2005 Wiley Periodicals, Inc. 杂原子化学 16:426–436, 2005; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI
• Synthesis of functionalized 2,3-dihydrothieno[2,3-d]pyrimidin-4(1H)-ones and their recyclization to 2,3-dihydrothieno[3,4-d]pyrimidin-4(1H)-ones
  作者：Mykhaylo V. Vovk、Volodymyr A. Sukach、Volodymyr V. Pyrozhenko、Andriy V. Bol'but

  DOI：10.1002/hc.20181

  日期：——

  By the reaction of 6-aryl(alkyl)amino-5-cyano-2,3-dihydro-1,3-thiazin-4(10)-ones with α-halogenoketones in the presence of triethylamine, 2,3-dihydrothieno[2,3-d]pyrimidin-4(1H)-ones have been synthesized and their acid-catalyzed recyclization to 2,3-dihydrothieno[3,4-d]pyrimidin-4(1H)-ones has been found and studied. © 2006 Wiley Periodicals, Inc. Heteroatom Chem 17:104–111, 2006; Published online

  通过 6-芳基(烷基)氨基-5-氰基-2,3-二氢-1,3-噻嗪-4(10)-酮与α-卤代酮在三乙胺、2,3-二氢噻吩[已经合成了 2,3-d]pyrimidin-4(1H)-ones，并发现并研究了它们在酸催化下再循环生成 2,3-dihydrothieno[3,4-d]pyrimidin-4(1H)-ones。© 2006 Wiley Periodicals, Inc. 杂原子化学 17:104–111, 2006; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20181
• Tandem One-pot Synthesis of Polysubstituted 1,3-Thiazine Derivatives
  作者：Shuliang Wang、Xiang Wang、Mansu Tu、Bo Jiang、Shujiang Tu

  DOI：10.1002/cjoc.201100067

  日期：2011.11

  AbstractA tandem one‐pot synthesis of polysubstituted 1,3‐thiazines has been developed by reacting with cyanoacetamide and isothiocyanate derivatives to give rise to 2‐cyano‐3‐mercaptoacrylamides, which are trapped in situ by various aldehydes or diversely substituted ketones through intermolecular cyclization, providing polysubstituted 1,3‐thiazine derivatives in short reaction times with good to excellent yields. The salient features of this novel protocol are operational simplicity, accessing the desired products from the readily available starting materials and easy of product isolation and may find wide spread applications in medicinal chemistry.