3-tert-butyl 5-(4-oxo-1-adamantyl) (4S,5R)-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-3,5-dicarboxylate | 1082059-98-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-tert-butyl 5-(4-oxo-1-adamantyl) (4S,5R)-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-3,5-dicarboxylate
• CAS: 1082059-98-0
• 化学式: C₃₂H₃₇NO₇
• 分子量: 547.648
• InChiKey: GFRSLBZLTWRASI-WWTXPZDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.76
• 重原子数：
  40.0
• 可旋转键数：
  5.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  91.37
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  3-tert-butyl 5-(4-oxo-1-adamantyl) (4S,5R)-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-3,5-dicarboxylate 在 sodium tetrahydroborate 作用下， 以 乙醚 为溶剂， 反应 10.0h， 生成 3-tert-butyl 5-(cis-4-hydroxy-1-adamantyl) (4S,5R)-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-3,5-dicarboxylate 、 3-tert-butyl 5-(trans-4-hydroxy-1-adamantyl) (4S,5R)-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-3,5-dicarboxylate
  参考文献：
  名称：

  Design, synthesis, and bioactivity of putative tubulin ligands with adamantane core

  摘要：

  Several adamantane-based taxol mimetics were synthesized and found to be cytotoxic at micromolar concentrations and to cause tubulin aggregation. The extent of the aggregation is maximal for N-benzoyl(2R,3S)-phenylisoseryloxyadamantane (5) and is very sensitive to the structural modi. cations. A hybrid compound (15), combining adamantane-based taxol mimetic with colchicine was synthesized and found to possess both microtubule depolymerizing and microtubule bundling activities in A549 human lung carcinoma cells. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.07.116
• 作为产物：
  描述：

  5-羟基-2-金刚烷酮 、 (4S,5R)-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以46%的产率得到3-tert-butyl 5-(4-oxo-1-adamantyl) (4S,5R)-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-3,5-dicarboxylate
  参考文献：
  名称：

  Design, synthesis, and bioactivity of putative tubulin ligands with adamantane core

  摘要：

  Several adamantane-based taxol mimetics were synthesized and found to be cytotoxic at micromolar concentrations and to cause tubulin aggregation. The extent of the aggregation is maximal for N-benzoyl(2R,3S)-phenylisoseryloxyadamantane (5) and is very sensitive to the structural modi. cations. A hybrid compound (15), combining adamantane-based taxol mimetic with colchicine was synthesized and found to possess both microtubule depolymerizing and microtubule bundling activities in A549 human lung carcinoma cells. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.07.116