(2E,5Z)-(5-Ethoxycarbonylmethylidene-4-oxothiazolidin-2-ylidene)-1-phenylethanone | 235423-21-9

• 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: (2E,5Z)-(5-Ethoxycarbonylmethylidene-4-oxothiazolidin-2-ylidene)-1-phenylethanone
• 英文别名: ethyl (2Z)-2-[(2E)-4-oxo-2-phenacylidene-1,3-thiazolidin-5-ylidene]acetate
• CAS: 235423-21-9
• 化学式: C₁₅H₁₃NO₄S
• 分子量: 303.339
• InChiKey: CEJOKGROFIUVBD-SIMOKGRJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  97.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2E,5Z)-(5-Ethoxycarbonylmethylidene-4-oxothiazolidin-2-ylidene)-1-phenylethanone 以 乙醇 为溶剂， 生成 (2Z,5Z)-(5-Ethoxycarbonylmethylidene-4-oxothiazolidin-2-ylidene)-1-phenylethanone
  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：

  (Z)-(5-ethoxycarbonylmethyl-4-oxothiazolidin-2-ylidene)-1-phenylethanone 在 溴 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 0.17h， 生成 (2E,5Z)-(5-Ethoxycarbonylmethylidene-4-oxothiazolidin-2-ylidene)-1-phenylethanone
  参考文献：
  名称：

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

  摘要：

  DOI：

文献信息

• 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。
• Stereo- and regiocontrol of electrophile-initiated rearrangement of push–pull 5-substituted 4-oxothiazolidine derivatives
  作者：Rade Marković、Zdravko Džambaski、Marija Baranac

  DOI：10.1016/s0040-4020(01)00496-3

  日期：2001.7

  Regioselective a-bromination of (Z)-5-substituted-2-alkylidene-4-oxothiazolidine derivatives affords, under mild experimental conditions, vinyl bromides 3 in good yields. They undergo rearrangement providing a highly efficient route to the stereodefined 4-oxo-thiazolidine derivatives possessing two fully delocalized exocyclic double bonds at C(2) and C(5) positions. A mechanism of this novel rearrangement reaction via base-promoted proton transfer from one carbanionic site to another, followed by the bromination-dehydrobromination sequence, is proposed. (C) 2001 Elsevier Science Ltd. All rights reserved.