N-(5-{2,3-dichloro-1-[dimethyl(1,1,2-trimethylpropyl)silanyloxy]propyl}-thiazol-2-yl)-2,2-dimethylpropionamide | 458530-80-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(5-{2,3-dichloro-1-[dimethyl(1,1,2-trimethylpropyl)silanyloxy]propyl}-thiazol-2-yl)-2,2-dimethylpropionamide
• 英文别名: N-[5-[(1R,2R)-2,3-dichloro-1-[2,3-dimethylbutan-2-yl(dimethyl)silyl]oxypropyl]-1,3-thiazol-2-yl]-2,2-dimethylpropanamide
• CAS: 458530-80-8
• 化学式: C₁₉H₃₄Cl₂N₂O₂SSi
• 分子量: 453.549
• InChiKey: LACOWWXJBWOQGV-ZFWWWQNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.67
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  79.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(5-{2,3-dichloro-1-[dimethyl(1,1,2-trimethylpropyl)silanyloxy]propyl}-thiazol-2-yl)-2,2-dimethylpropionamide 在 palladium on activated charcoal 盐酸 、 sodium azide 、 氢气 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 80.0 ℃ 、101.33 kPa 条件下， 反应 36.0h， 生成 5-(3-amino-2-chloroprop-1-enyl)thiazol-2-ylamine dihydrochloride
  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)-[dimethyl(1,1,2-trimethylpropyl)silanyloxy]methyl}-thiazol-2-yl)-2,2-dimethylpropionamide 在 N-氯代丁二酰亚胺 、 对甲苯磺酸 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 156.0h， 生成 N-(5-{2,3-dichloro-1-[dimethyl(1,1,2-trimethylpropyl)silanyloxy]propyl}-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

文献信息

• Synthesis of 5-deazathiogirollines: analogs of a natural antitumor agent
  作者：Bruno Schiavi、Alain Ahond、Ali Al-Mourabit、Christiane Poupat、Angèle Chiaroni、Christiane Gaspard、Pierre Potier

  DOI：10.1016/s0040-4020(02)00383-6

  日期：2002.5

  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.