(Z)-(5-ethoxycarbonylmethyl-4-oxothiazolidin-2-ylidene)-N-(2-phenylethyl)ethanamide | 204690-22-2

• 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: (Z)-(5-ethoxycarbonylmethyl-4-oxothiazolidin-2-ylidene)-N-(2-phenylethyl)ethanamide
• 英文别名: (Z)-(5-Ethoxycarbonylmethyl-4-oxothiazolidin-2-ylidene)-N-phenylethylethanamide；(Z)-2-(5-ethoxycarbonylmethyl-4-oxothiazolidin-2-ylidene)-N-(2-phenylethyl)ethanamide；(Z)-ethyl 4-oxo-2-[2-oxo-2-[(2-phenylethyl)-amino]ethylidene]-5-thiazolidineacetate；ethyl 2-[(2Z)-4-oxo-2-[2-oxo-2-(2-phenylethylamino)ethylidene]-1,3-thiazolidin-5-yl]acetate
• CAS: 204690-22-2
• 化学式: C₁₇H₂₀N₂O₄S
• 分子量: 348.423
• InChiKey: MCYPAIAFVCINBE-PTNGSMBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  110
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (Z)-(5-ethoxycarbonylmethyl-4-oxothiazolidin-2-ylidene)-N-(2-phenylethyl)ethanamide 在 溴 作用下， 以 氘代二甲亚砜 、 乙醇 为溶剂， 反应 240.17h， 生成 (E)-(5-ethoxycarbonylmethyl-4-oxothiazolidin-2-ylidene)-N-(2-phenylethyl)-2-bromoethanamide
  参考文献：
  名称：

  Marković, Rade; Baranac, Marija, Synlett, 2000, # 5, p. 607 - 610

  摘要：

  DOI：
• 作为产物：
  描述：

  2-巯基丁二酸二乙酯 、 2-氰基苯乙基乙酰胺 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 以29%的产率得到(Z)-(5-ethoxycarbonylmethyl-4-oxothiazolidin-2-ylidene)-N-(2-phenylethyl)ethanamide
  参考文献：
  名称：

  分子间和分子内RAHB控制的推挽式噻唑烷酮衍生物的构型异构化：1 H NMR浓度和温度效应的动态研究

  摘要：

  1 H NMR光谱用于研究极性和非极性溶剂中与结构相关的（Z）-和（E）-5-取代的-2-亚烷基-4-氧噻唑烷中的氢键。这些典型的推挽式烯烃的平衡混合物由分子内H键合的E型异构体和分子间H键合的Z型异构体组成，其比例取决于溶剂的极性。对于该系列的代表（E）-（5-乙氧基羰基甲基-4-氧杂噻唑烷-2-亚基）-1-苯基乙酮（1），缺乏大的化学NH位移（δ12.06 ppm）的浓度和温度依赖性）在CDCl 3中表示强烈的分子内共振辅助氢键形成（RAHB）。（Z）-1异构体的NH质子的高场化学位移随温度升高和1 H NMR较大的Δδ/ ΔT值（-11.82 ppb°C -1，Z / E = 60：40 ，CDCl 3中的-或-10.33 ppb°C -1，Z / E = 20：80 ）的解释是分子间氢键的减少，导致大量的游离或未缔合的Z-异构体。版权所有©2004 John Wiley＆Sons，Ltd

  DOI：

  10.1002/poc.700

文献信息

• 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。
• Regioselective Reduction of 5-Substituted 2-Alkylidene-4-Oxothiazolidines by Metal Hydrides
  作者：Rade Marković、Marija Baranac、Milovan Stojanović

  DOI：10.1055/s-2004-820051

  日期：——

  acetate substituent were chemoselectively reduced to corresponding alcohols, or new condensed 2-alkylidenethiazolidines. The method is based on the resistance of an enaminone fragment to reduction by metal hydrides.

  具有 5-取代乙酸酯取代基的噻唑烷 β-烯氨基衍生物被化学选择性地还原为相应的醇，或新的缩合 2-亚烷基噻唑烷。该方法基于烯胺酮片段对金属氢化物还原的抵抗力。
• Sequential Bromination-Rearrangement of Push-Pull Thiazolidines Induced by Pyridinium Hydrobromide Perbromide under Homogenous Reaction Conditions
  作者：Rade Markovic、Marija Baranac、Zdravko Dzambaski

  DOI：10.3987/com-03-9980

  日期：——

  Regiospecific bromination-rearrangement of the 5-substituted 2-alkylidene-4-oxothiazolidine derivatives induced by pyridinium hydrobromide perbromide (PHBP) provides a new synthetic approach to the corresponding push-pullthiazolidines with two exocyclic double bonds. In comparison to a heterogenous alternative, this conversion, taking place in acetonitrile under homogenous reaction conditions, has

  由过溴氢溴酸吡啶 (PHBP) 诱导的 5-取代的 2-亚烷基-4-氧代噻唑烷衍生物的区域特异性溴化重排为具有两个环外双键的相应推拉噻唑烷提供了一种新的合成方法。与非均相替代方案相比，这种转化在均相反应条件下在乙腈中发生，具有几乎定量产率和显着提高速率的优点。
• High regioselectivity in the heterocyclization of β-oxonitriles to 4-oxothiazolidines: X-ray structure proof
  作者：Rade Marković、Marija Baranac、Zdravko Džambaski、Milovan Stojanović、Peter J Steel

  DOI：10.1016/s0040-4020(03)01146-3

  日期：2003.9

  Base-catalyzed reactions of beta-oxonitriles 1 with diethyl mercaptosuccinate favour heterocyclization to afford 2-alkylidene-4-oxothiazolidines 3, rather than 2-alkylidene-4-oxo-1,3-thiazinanes 4. The observed regioselectivity is based on spectroscopic and experimental evidence, including a single-crystal X-ray structure determination. (C) 2003 Elsevier Ltd. All rights reserved.
• Regioselective Synthesis and Spectral Characterization of Ethyl (Z)- and (E)-2-Alkylidene-4-oxothiazolidine-5-acetate Derivatives. Solvent Effects on the Z-E Isomerization
  作者：Rade Markovic、Marija Baranac

  DOI：10.3987/com-97-8094

  日期：——

  The title compounds containing an exocyclic double bond of exclusively the Z-configuration were prepared in anhydrous ethanol by the regioselective base catalyzed reaction of diethyl 2-mercaptobutanedioate with nitrile precursors possessing an acidic a-hydrogen. The H-1 NMR data indicating the presence of both geometrical isomers in primarily nonpolar media favoring the form are presented in terms of the solvent influence on intra- and intermolecular H-bonding and stereochemical outcome of the reaction.