5,7-di-tert-butyl-2-(dimethylamino)benzo[d][1,2]oxaphosphol-3(2H)-oxime | 1448643-79-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 5,7-di-tert-butyl-2-(dimethylamino)benzo[d][1,2]oxaphosphol-3(2H)-oxime
• CAS: 1448643-79-5
• 化学式: C₁₇H₂₇N₂O₂P
• 分子量: 322.387
• InChiKey: VVDMYUSCVRGQAS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  22.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  48.97
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5,7-di-tert-butyl-2-(dimethylamino)benzo[d][1,2]oxaphosphol-3(2H)-oxime 在 双氧水 作用下， 以 四氢呋喃 为溶剂， 以75%的产率得到5,7-di-tert-butyl-2-(dimethylamino)benzo[d][1,2]oxaphosphone-3(2H)-oxime
  参考文献：
  名称：

  Antineoplastic activity of fused nitrogen-phosphorus heterocycles and derived phosphonates

  摘要：

  A variety of derivatives incorporating substituted heterocycle-phosphor motifs is described. Substituted N,P-heterocycles and derived phosphonates were produced efficiently in a tandem operation without intermediate isolation. The synthesis methodology is based on the reaction of dialkyl phosphites with Schiff base Kabachnik-Fields intermediates, which are generated in situ from 2-amino-4,6-di-tert-butylphenol and substituted benzaldehydes in dry THF/FeCl3 (10 %) solution, to yield fused oxazole-2-phosphonates in moderate yield (a parts per thousand 55 %). The latter products could be also obtained in excellent yield (a parts per thousand yen76 %) by directly applying the same P(III) reagents to the parent Schiff bases. On the other hand, oxazaphosphinine-2-amines were isolated in high yields (a parts per thousand 77 %) when the Schiff bases were allowed to react with hexaalkyltriamidophosphites at rt. More P-heterocycles and the derived phosphonates were also obtained when the same reagents were applied to another imino derivative derived from the aminophenol, 2-hydroxybenzaldehyde oxime. The synthesized scaffolds were biologically evaluated and found to possess potent anticancer activities. On the basis of bioassay data, the produced N,P-heterocycles exhibit remarkable antitumor activity against 17 tested human tumor cell lines, representing breast and prostate cancer and melanoma. Several phosphonates were found to possess specific anti-breast cancer activity (especially MDA-MB-435 cell lines) while others possess specific effects against melanoma (MI4 and SK-MEL-2 cancer cell lines). These findings form a foundation for further investigation in our continuing efforts to develop selective anticancer agents..

  DOI：

  10.1007/s00706-013-0950-6
• 作为产物：
  描述：

  3,5-二叔丁基水杨醛 在 盐酸羟胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 10.0h， 生成 5,7-di-tert-butyl-2-(dimethylamino)benzo[d][1,2]oxaphosphol-3(2H)-oxime
  参考文献：
  名称：

  Antineoplastic activity of fused nitrogen-phosphorus heterocycles and derived phosphonates

  摘要：

  A variety of derivatives incorporating substituted heterocycle-phosphor motifs is described. Substituted N,P-heterocycles and derived phosphonates were produced efficiently in a tandem operation without intermediate isolation. The synthesis methodology is based on the reaction of dialkyl phosphites with Schiff base Kabachnik-Fields intermediates, which are generated in situ from 2-amino-4,6-di-tert-butylphenol and substituted benzaldehydes in dry THF/FeCl3 (10 %) solution, to yield fused oxazole-2-phosphonates in moderate yield (a parts per thousand 55 %). The latter products could be also obtained in excellent yield (a parts per thousand yen76 %) by directly applying the same P(III) reagents to the parent Schiff bases. On the other hand, oxazaphosphinine-2-amines were isolated in high yields (a parts per thousand 77 %) when the Schiff bases were allowed to react with hexaalkyltriamidophosphites at rt. More P-heterocycles and the derived phosphonates were also obtained when the same reagents were applied to another imino derivative derived from the aminophenol, 2-hydroxybenzaldehyde oxime. The synthesized scaffolds were biologically evaluated and found to possess potent anticancer activities. On the basis of bioassay data, the produced N,P-heterocycles exhibit remarkable antitumor activity against 17 tested human tumor cell lines, representing breast and prostate cancer and melanoma. Several phosphonates were found to possess specific anti-breast cancer activity (especially MDA-MB-435 cell lines) while others possess specific effects against melanoma (MI4 and SK-MEL-2 cancer cell lines). These findings form a foundation for further investigation in our continuing efforts to develop selective anticancer agents..

  DOI：

  10.1007/s00706-013-0950-6