(2Z)-2-(4-oxo-1,3-thiazolidin-2-ylidene)-N-phenylacetamide | 185739-18-8

• 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: (2Z)-2-(4-oxo-1,3-thiazolidin-2-ylidene)-N-phenylacetamide
• CAS: 185739-18-8
• 化学式: C₁₁H₁₀N₂O₂S
• 分子量: 234.279
• InChiKey: BBDQBDCUDIEPIZ-WDZFZDKYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  83.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2Z)-2-(4-oxo-1,3-thiazolidin-2-ylidene)-N-phenylacetamide 在 溴 作用下， 以 氯仿 为溶剂， 生成 (Z/E)-2-bromo-2-[4-oxothiazolidin-2-ylidene]-N-phenylacetamide
  参考文献：
  名称：

  含有 4-氧代噻唑烷部分的取代和未取代吡啶鎓盐的高产率合成

  摘要：

  通过 2-(1-溴亚烷基) thiazolidin-4-ones 的有效重排，制备了一系列带有 4-氧代噻唑烷基部分的新的未取代和取代的吡啶鎓盐。该过程基于三个步骤，即碳-溴裂解、溴转移和取代，每个步骤均由吡啶或其衍生物作为碱和反应物诱导。

  DOI：

  10.1055/s-2008-1067113
• 作为产物：
  描述：

  (Z/E)-2-bromo-2-[4-oxothiazolidin-2-ylidene]-N-phenylacetamide 在 水 、 potassium thioacetate 作用下， 以 丙酮 为溶剂， 反应 24.0h， 以72%的产率得到(2Z)-2-(4-oxo-1,3-thiazolidin-2-ylidene)-N-phenylacetamide
  参考文献：
  名称：

  中性和阴离子亲核试剂的亲油攻击引发的2-亚烷基-4-氧噻唑烷乙烯基溴的转化

  摘要：

  衍生自2-亚烷基-4-氧噻唑烷的乙烯基溴代表一类乙烯基卤，它们容易受到一系列亲核试剂的亲溴攻击。的Ph 3 P，ACS -，CN - ，我-，F -，AC 2 CH -和N 3 -攻击末端了还原脱溴，而溴取代发生与KSCN。当乙酸根阴离子和有机碱（例如吡啶，Et 3 N或吗啉）用作亲核试剂时，最初的亲溴性攻击随后是溴迁移到环的C（5）位置，从而使C（5）官能化杂环系统。

  DOI：

  10.1016/j.tet.2010.06.057

文献信息

• 2-Alkylidene-4-oxothiazolidine S-oxides: synthesis and stereochemistry
  作者：Zdravko Džambaski、Rade Marković、Erich Kleinpeter、Marija Baranac-Stojanović

  DOI：10.1016/j.tet.2013.05.087

  日期：2013.8

  A series of 5-unsubstituted and 5-substituted 2-alkylidene-4-oxothiazolidine-S-oxides were synthesized by the sulfur-oxidation with m-CPBA. The stereochemistry of 5-substituted sulfoxides was determined by means of NMR spectroscopy and DFT theoretical calculations. It was found that the thermodynamically less stable anti-isomer was initially formed in the course of the oxidation, but it underwent epimerization

  一系列5-未取代的和的5-取代的2-亚烷基-4- oxothiazolidine-小号-oxides是由硫氧化与合成米-CPBA。通过NMR光谱和DFT理论计算确定5-取代的亚砜的立体化学。据发现，热力学不太稳定的抗最初形成在氧化过程中异构体，但它经历差向异构化至该混合物中更稳定的富集顺式异构体，在工作过程。顺式异构体的较高稳定性归因于较强的超共轭σC –H →σ* S-O相互作用，而较弱的σC –C →σ*S-O在其反配体中的离域化以及分子内1,5-CH = O氢键的存在。
• Synthesis of 4-(4-oxo-1,3-thiazolidin-2-ylidene)-pyrrolidine-2,3,5-triones
  作者：Konstantin L. Obydennov、Aleksei N. Galushchinskiy、Marya F. Kosterina、Tatiana V. Glukhareva、Yuri Yu. Morzherin

  DOI：10.1007/s10593-017-2102-0

  日期：2017.5

  It was shown that 2-(1,3-thiazolidin-2-ylidene)acetamides can be used as 2-enamides in cyclocondensation reactions with oxalyl chloride, leading to the formation of new heterocyclic assemblies – 4-(4-oxo-1,3-thiazolidin-2-ylidene)pyrrolidine-2,3,5-triones in 50–88% yields.

  结果表明，在与草酰氯的环缩合反应中，2-（1,3-噻唑烷-2-亚甲基）乙酰胺可用作2-酰胺，导致形成新的杂环组装体– 4-（4-oxo-1， 3-噻唑烷-2--2-亚基）吡咯烷-2,3,5-三酮的产率为50-88％。
• A novel and efficient 4-oxothiazolidine-1,2-dithiole rearrangement induced by Lawesson's reagent
  作者：Rade Markovic、Marija Baranac、Stanka Jovetic

  DOI：10.1016/s0040-4039(03)01721-0

  日期：2003.9

  Functionalized 1,2-dithioles have been synthesized by a ring opening–closing process of 5-substituted- and 5-unsubstituted-2-alkylidene-4-oxothiazolidines with Lawesson's reagent. The 13C NMR data confirmed the meso-ionic structure of these aromatic-type 1,2-dithioles.

  功能化的1,2-二硫醇是通过Lawesson试剂通过5-取代的和5-未取代的-2-亚烷基-4-氧噻唑烷的开环过程合成的。的13个C NMR数据证实了内消旋这些芳香型1,2- dithioles的-ionic结构。
• Studies of the regioselective ring-opening–closing mode of functionally different thiazolidine type enaminones: en route to the synthesis of trithiaazapentalene derivatives
  作者：Aleksandar Rašović、Andreas Koch、Erich Kleinpeter、Rade Marković

  DOI：10.1016/j.tet.2013.10.088

  日期：2013.12

  Trithiaazapentalene derivatives were prepared by the reaction of 2-alkylidene-4-oxothiazolidines with Lawesson's reagent. They are classified as two structurally different trithiaazapentalene compounds that have different contributions of monocyclic 1,2-dithiole and 1,2,4-dithiazole structures and degrees of aromaticity of the bicyclic trithiaazapentalene system. The electron-donating ability of substituents at the C(5) position of the trithiaazapentalene system is recognized as the main cause for changes in pi-Celectron distribution. This is the first complete study of substituent effects on the structure of trithiapentalenes. (C) 2013 Elsevier Ltd. All rights reserved.
• Transformations of 2-alkylidene-4-oxothiazolidine vinyl bromides initiated by bromophilic attack of neutral and anionic nucleophiles
  作者：Marija Baranac-Stojanović、Jovana Tatar、Milovan Stojanović、Rade Marković

  DOI：10.1016/j.tet.2010.06.057

  日期：2010.8

  Vinyl bromides derived from 2-alkylidene-4-oxothiazolidines represent a class of vinyl halides, which readily undergo a bromophilic attack by a range of nucleophiles. With Ph3P, AcS−, CN−, I−, F−, Ac2CH− and N3− the attack ends up with reductive debromination, whereas the bromine substitution takes place with KSCN. When acetate anion and organic bases, such as pyridine, Et3N or morpholine, are employed

  衍生自2-亚烷基-4-氧噻唑烷的乙烯基溴代表一类乙烯基卤，它们容易受到一系列亲核试剂的亲溴攻击。的Ph 3 P，ACS -，CN - ，我-，F -，AC 2 CH -和N 3 -攻击末端了还原脱溴，而溴取代发生与KSCN。当乙酸根阴离子和有机碱（例如吡啶，Et 3 N或吗啉）用作亲核试剂时，最初的亲溴性攻击随后是溴迁移到环的C（5）位置，从而使C（5）官能化杂环系统。