N-{5-[(2,2-dimethyl-[1,3]dioxolan-4-yl)-(S)-hydroxy-methyl]-thiazol-2-yl}-2,2-dimethylpropionamide | 458530-72-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-{5-[(2,2-dimethyl-[1,3]dioxolan-4-yl)-(S)-hydroxy-methyl]-thiazol-2-yl}-2,2-dimethylpropionamide
• 英文别名: N-[5-[(S)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-hydroxymethyl]-1,3-thiazol-2-yl]-2,2-dimethylpropanamide
• CAS: 458530-72-8
• 化学式: C₁₄H₂₂N₂O₄S
• 分子量: 314.406
• InChiKey: QZWKRYWZPGEOAR-SCZZXKLOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-{5-[(2,2-dimethyl-[1,3]dioxolan-4-yl)-(S)-hydroxy-methyl]-thiazol-2-yl}-2,2-dimethylpropionamide 在 咪唑 、 sodium methylate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 N-(5-{(2,2-dimethyl-[1,3]dioxolan-4-yl)-[dimethyl(1,1,2-trimethylpropyl)silanyloxy]methyl}-thiazol-2-yl)-2,2-dimethylpropionamide
  参考文献：
  名称：

  Synthesis of 5-deazathiogirollines: analogs of a natural antitumor agent

  摘要：

  2-Aminothiazole analogs of the natural antitumor agent, girolline, were prepared in natural stereochemistry series (threo) and in a non-natural series (erythro). The key-step involved a coupling reaction between 2,3-O-isopropylidene-D-glyceraldehyde and a properly protected 2-aminothiazole, via a dianion species, The biological activity of the prepared analogs was evaluated on human cancer cells to determine structure-activity relationship. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00383-6
• 作为产物：
  描述：

  N-{5-[(2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-thiazol-2-yl}-2,2-dimethylpropionamide 在 manganese(IV) oxide 、 L-Selectride 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 生成 N-{5-[(2,2-dimethyl-[1,3]dioxolan-4-yl)-(S)-hydroxy-methyl]-thiazol-2-yl}-2,2-dimethylpropionamide
  参考文献：
  名称：

  Synthesis of 5-deazathiogirollines: analogs of a natural antitumor agent

  摘要：

  2-Aminothiazole analogs of the natural antitumor agent, girolline, were prepared in natural stereochemistry series (threo) and in a non-natural series (erythro). The key-step involved a coupling reaction between 2,3-O-isopropylidene-D-glyceraldehyde and a properly protected 2-aminothiazole, via a dianion species, The biological activity of the prepared analogs was evaluated on human cancer cells to determine structure-activity relationship. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00383-6