N-[(3R,5S)-2-oxo-5-phenyltetrahydrofuran-3-yl]dodecanamide | 1450759-40-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-[(3R,5S)-2-oxo-5-phenyltetrahydrofuran-3-yl]dodecanamide
• 英文别名: N-[(3R,5S)-2-oxo-5-phenyloxolan-3-yl]dodecanamide
• CAS: 1450759-40-6
• 化学式: C₂₂H₃₃NO₃
• 分子量: 359.509
• InChiKey: JKHBCDQBYVTDHU-UXHICEINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  26
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-[(3R,5S)-2-oxo-5-phenyltetrahydrofuran-3-yl]dodecanamide 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 20.0h， 以93%的产率得到N-[(1R,3S)-3-羟基-1-(羟甲基)-3-苯基丙基]十二酰胺
  参考文献：
  名称：

  Synthesis of Potent CERT Inhibitor HPA-12 Featuring a Tandem Corey-Link and Intramolecular Nucleophilic Acyl Substitution Reaction

  摘要：

  A novel preparation of the potent CERT protein inhibitor (1R,3S)-HPA-12 is described. The synthesis is accomplished in five steps from (S)-Wynberg lactone and features a diastereoselective tandem Corey-Link and intramolecular nucleophilic acyl substitution reaction in a key step.

  DOI：

  10.1055/s-0033-1338495
• 作为产物：
  描述：

  (S)-4,4,4-trichloro-3-hydroxy-1-phenyl-1-butanone 在 sodium azide 、 三苯基膦 、 sodium hydroxide 、 tetramethylammonium triacetoxyborohydride 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 水 、 溶剂黄146 、 乙腈 为溶剂， 反应 78.0h， 生成 N-[(3R,5S)-2-oxo-5-phenyltetrahydrofuran-3-yl]dodecanamide
  参考文献：
  名称：

  Synthesis of Potent CERT Inhibitor HPA-12 Featuring a Tandem Corey-Link and Intramolecular Nucleophilic Acyl Substitution Reaction

  摘要：

  A novel preparation of the potent CERT protein inhibitor (1R,3S)-HPA-12 is described. The synthesis is accomplished in five steps from (S)-Wynberg lactone and features a diastereoselective tandem Corey-Link and intramolecular nucleophilic acyl substitution reaction in a key step.

  DOI：

  10.1055/s-0033-1338495

文献信息

• Synthesis of Potent CERT Inhibitor HPA-12 Featuring a Tandem Corey-Link and Intramolecular Nucleophilic Acyl Substitution Reaction
  作者：Timothy Snowden、Jason Snider、Jordan Entrekin、Debra Dolliver

  DOI：10.1055/s-0033-1338495

  日期：——

  A novel preparation of the potent CERT protein inhibitor (1R,3S)-HPA-12 is described. The synthesis is accomplished in five steps from (S)-Wynberg lactone and features a diastereoselective tandem Corey-Link and intramolecular nucleophilic acyl substitution reaction in a key step.