(Z)-(5-ethoxycarbonylmethyl-4-oxothiazolidin-2-ylidene)-N-(phenyl)-2-bromoethanamide | 285133-47-3

• 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-(phenyl)-2-bromoethanamide
• 英文别名: (Z)-2-bromo-2-(5-ethoxycarbonylmethyl-4-oxothiazolidin-2-ylidene)-N-phenylethanamide；ethyl 2-[(2Z)-2-(2-anilino-1-bromo-2-oxoethylidene)-4-oxo-1,3-thiazolidin-5-yl]acetate
• CAS: 285133-47-3
• 化学式: C₁₅H₁₅BrN₂O₄S
• 分子量: 399.265
• InChiKey: RSQDKTBUQOHCQI-QINSGFPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 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-(phenyl)-2-bromoethanamide 在 氘代吡啶 作用下， 以 氘代氯仿 为溶剂， 生成 (2Z,5Z)-(5-ethoxycarbonylmethylidene-4-oxothiazolidin-2-ylidene)-N-phenylethanamide 、 (2E,5Z)-(5-ethoxycarbonylmethylidene-4-oxothiazolidin-2-ylidene)-N-phenylethanamide
  参考文献：
  名称：

  Stereo- and regiocontrol of electrophile-initiated rearrangement of push–pull 5-substituted 4-oxothiazolidine derivatives

  摘要：

  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.

  DOI：

  10.1016/s0040-4020(01)00496-3
• 作为产物：
  描述：

  (Z)-(5-ethoxycarbonylmethyl-4-oxothiazolidin-2-ylidene)-N-phenylethanamide 在 溴 、 silica gel 作用下， 以 四氯化碳 、 乙酸乙酯 、 甲苯 为溶剂， 反应 0.75h， 生成 (Z)-(5-ethoxycarbonylmethyl-4-oxothiazolidin-2-ylidene)-N-(phenyl)-2-bromoethanamide
  参考文献：
  名称：

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

  摘要：

  DOI：

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。