(4S,5S)-5-Allyl-4-cyclohexylmethyl-2-oxo-oxazolidine-3-carboxylic acid tert-butyl ester | 136057-67-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4S,5S)-5-Allyl-4-cyclohexylmethyl-2-oxo-oxazolidine-3-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (4S,5S)-4-(cyclohexylmethyl)-2-oxo-5-prop-2-enyl-1,3-oxazolidine-3-carboxylate
• CAS: 136057-67-5
• 化学式: C₁₈H₂₉NO₄
• 分子量: 323.433
• InChiKey: DNJCBEICSCGZOO-GJZGRUSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.66
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  55.84
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (4S,5S)-5-Allyl-4-cyclohexylmethyl-2-oxo-oxazolidine-3-carboxylic acid tert-butyl ester 在 ruthenium trichloride 、 sodium periodate 作用下， 以 四氯化碳 、 水 、 乙腈 为溶剂， 以82%的产率得到(4S,5S)-5-Carboxymethyl-4-cyclohexylmethyl-2-oxo-oxazolidine-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Lewis acid-promoted direct substitution of 4-methoxy- and 4-phenylthio-2-oxazolidinones by alkyl cuprates. Facile preparation of (3s,4s)-statine and (3s,4s)-cyclohexylstatine.

  摘要：

  Treatment of 4-methoxy- and 4-phenylthio-2-oxazolidinones with a combination of cuprates and BF3 results in smooth formation of 4-alkyl and 4-aryl derivatives in high yield. By this method, the titled compounds of biological interest are readily synthesized from (4S,5S)-5-allyl-4-methoxy (or 4-phenylthio)-2-oxazolidinones stereoselectively.

  DOI：

  10.1016/0040-4039(91)80822-n
• 作为产物：
  描述：

  trans-5-allyl-4-phenylthio-2-oxazolidinone 在 正丁基锂 、 三氟化硼乙醚 、 lithium chloride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 (4S,5S)-5-Allyl-4-cyclohexylmethyl-2-oxo-oxazolidine-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Lewis acid-promoted direct substitution of 4-methoxy- and 4-phenylthio-2-oxazolidinones by alkyl cuprates. Facile preparation of (3s,4s)-statine and (3s,4s)-cyclohexylstatine.

  摘要：

  Treatment of 4-methoxy- and 4-phenylthio-2-oxazolidinones with a combination of cuprates and BF3 results in smooth formation of 4-alkyl and 4-aryl derivatives in high yield. By this method, the titled compounds of biological interest are readily synthesized from (4S,5S)-5-allyl-4-methoxy (or 4-phenylthio)-2-oxazolidinones stereoselectively.

  DOI：

  10.1016/0040-4039(91)80822-n