N-(2,2-dimethoxyethyl)-2,2,2-trifluoro-N-(2-hydroxybenzyl)acetamide | 817160-27-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N-(2,2-dimethoxyethyl)-2,2,2-trifluoro-N-(2-hydroxybenzyl)acetamide
• 英文别名: N-(2,2-dimethoxyethyl)-2,2,2-trifluoro-N-[(2-hydroxyphenyl)methyl]acetamide
• CAS: 817160-27-3
• 化学式: C₁₃H₁₆F₃NO₄
• 分子量: 307.27
• InChiKey: ARAITJXSAHORTR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-(2,2-dimethoxyethyl)-2,2,2-trifluoro-N-(2-hydroxybenzyl)acetamide 在 三氟化硼乙醚 作用下， 以 乙醚 为溶剂， 反应 120.0h， 以49%的产率得到2-methoxy-N-trifluoroacetyl-2,3,4,5-tetrahydro-1,4-benzoxazepine
  参考文献：
  名称：

  Synthesis of tetrahydrobenzoxazepine acetals with electron-withdrawing groups on the nitrogen atom. Novel scaffolds endowed with anticancer activity against breast cancer cells

  摘要：

  Synthetic approaches that have led to (RS)-3-methoxy-N-substituded-1,2,3,5-tetrahydro-4,1-benzoxazepines with different electron-withdrawing groups, and (RS)-2-methoxy-N-trifluoroacetyl-2,3,4,5-tetrahydro-1,4-benzoxazepine are described. These novel synthons that were designed to be used as scaffolds for the preparation of new 0,N-acetals as anticancer agents, unexpectedly proved to show antiproliferative activity against the MCF-7 breast cancer cell line. It has been found that substituents on the nitrogen atom have an influence on biological activity. In particular, the presence of a trifluoroacetyl moiety on the nitrogen atom leads to amides displaying interesting in vitro antitumour activities. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.09.072
• 作为产物：
  描述：

  1-(三氟甲基)乙酰基苯并三唑 、 2-(2-hydroxybenzylamino)acetaldehyde dimethyl acetal 以 四氢呋喃 为溶剂， 反应 3.0h， 以72%的产率得到N-(2,2-dimethoxyethyl)-2,2,2-trifluoro-N-(2-hydroxybenzyl)acetamide
  参考文献：
  名称：

  Synthesis of tetrahydrobenzoxazepine acetals with electron-withdrawing groups on the nitrogen atom. Novel scaffolds endowed with anticancer activity against breast cancer cells

  摘要：

  Synthetic approaches that have led to (RS)-3-methoxy-N-substituded-1,2,3,5-tetrahydro-4,1-benzoxazepines with different electron-withdrawing groups, and (RS)-2-methoxy-N-trifluoroacetyl-2,3,4,5-tetrahydro-1,4-benzoxazepine are described. These novel synthons that were designed to be used as scaffolds for the preparation of new 0,N-acetals as anticancer agents, unexpectedly proved to show antiproliferative activity against the MCF-7 breast cancer cell line. It has been found that substituents on the nitrogen atom have an influence on biological activity. In particular, the presence of a trifluoroacetyl moiety on the nitrogen atom leads to amides displaying interesting in vitro antitumour activities. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.09.072

文献信息

• Synthesis of tetrahydrobenzoxazepine acetals with electron-withdrawing groups on the nitrogen atom. Novel scaffolds endowed with anticancer activity against breast cancer cells
  作者：Mónica Díaz-Gavilán、Fernando Rodríguez-Serrano、José A. Gómez-Vidal、Juan A. Marchal、Antonia Aránega、Miguel Á. Gallo、Antonio Espinosa、Joaquín M. Campos

  DOI：10.1016/j.tet.2004.09.072

  日期：2004.12

  Synthetic approaches that have led to (RS)-3-methoxy-N-substituded-1,2,3,5-tetrahydro-4,1-benzoxazepines with different electron-withdrawing groups, and (RS)-2-methoxy-N-trifluoroacetyl-2,3,4,5-tetrahydro-1,4-benzoxazepine are described. These novel synthons that were designed to be used as scaffolds for the preparation of new 0,N-acetals as anticancer agents, unexpectedly proved to show antiproliferative activity against the MCF-7 breast cancer cell line. It has been found that substituents on the nitrogen atom have an influence on biological activity. In particular, the presence of a trifluoroacetyl moiety on the nitrogen atom leads to amides displaying interesting in vitro antitumour activities. (C) 2004 Elsevier Ltd. All rights reserved.