(Z)-(5-(2-hydroxyethyl)-3-methyl-4-oxothiazolidin-2-ylidene)-1-phenylethanone | 791819-58-4

• 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-(2-hydroxyethyl)-3-methyl-4-oxothiazolidin-2-ylidene)-1-phenylethanone
• 英文别名: (2Z)-5-(2-hydroxyethyl)-3-methyl-2-phenacylidene-1,3-thiazolidin-4-one
• CAS: 791819-58-4
• 化学式: C₁₄H₁₅NO₃S
• 分子量: 277.344
• InChiKey: WKYOYSZMULFYKJ-LCYFTJDESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  82.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-(5-(2-hydroxyethyl)-3-methyl-4-oxothiazolidin-2-ylidene)-1-phenylethanone 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以56%的产率得到cis-(Z)-(3-methyltetrahydrofuro[2,3-d]thiazol-2(3H)-ylidene)-1-phenylethanone
  参考文献：
  名称：

  Stereocontrolled Synthesis of New Tetrahydrofuro[2,3-d]thiazole Derivatives via Activated Vinylogous Iminium Ions

  摘要：

  Heterocyclization of (Z)-5-(2-hydroxyethyl)-3-methyl-4-oxothiazolidines, bearing electron-withdrawing groups conjugated to an exocyclic double bond at C(2)-position, afforded under reductive conditions, cis-tetrahydroftiro[2,3-d]thiazole derivatives. The reactions of these functionalized push-pull beta-enamines occur in a stereocontrolled fashion via activated vinylogous N-methyliminium ions, which are trapped by an internal hydroxyethyl group.

  DOI：

  10.3987/com-05-10494
• 作为产物：
  描述：

  碘甲烷 、 (Z)-[5-(2-hydroxyethyl)-4-oxothiazolidin-2-ylidene]-1-phenylethanone 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 以86%的产率得到(Z)-(5-(2-hydroxyethyl)-3-methyl-4-oxothiazolidin-2-ylidene)-1-phenylethanone
  参考文献：
  名称：

  Stereocontrolled Synthesis of New Tetrahydrofuro[2,3-d]thiazole Derivatives via Activated Vinylogous Iminium Ions

  摘要：

  Heterocyclization of (Z)-5-(2-hydroxyethyl)-3-methyl-4-oxothiazolidines, bearing electron-withdrawing groups conjugated to an exocyclic double bond at C(2)-position, afforded under reductive conditions, cis-tetrahydroftiro[2,3-d]thiazole derivatives. The reactions of these functionalized push-pull beta-enamines occur in a stereocontrolled fashion via activated vinylogous N-methyliminium ions, which are trapped by an internal hydroxyethyl group.

  DOI：

  10.3987/com-05-10494

文献信息

• 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。
• Stereocontrolled Synthesis of New Tetrahydrofuro[2,3-d]thiazole Derivatives via Activated Vinylogous Iminium Ions
  作者：Rade Markovic、Marija Baranac、Peter Steel、Erich Kleinpeter、Milovan Stojanovic

  DOI：10.3987/com-05-10494

  日期：——

  Heterocyclization of (Z)-5-(2-hydroxyethyl)-3-methyl-4-oxothiazolidines, bearing electron-withdrawing groups conjugated to an exocyclic double bond at C(2)-position, afforded under reductive conditions, cis-tetrahydroftiro[2,3-d]thiazole derivatives. The reactions of these functionalized push-pull beta-enamines occur in a stereocontrolled fashion via activated vinylogous N-methyliminium ions, which are trapped by an internal hydroxyethyl group.