(E)-2-Oxo-dec-3-enoic acid (1S,2R)-2-phenyl-cyclohexyl ester | 201798-56-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-2-Oxo-dec-3-enoic acid (1S,2R)-2-phenyl-cyclohexyl ester
• CAS: 201798-56-3
• 化学式: C₂₂H₃₀O₃
• 分子量: 342.478
• InChiKey: JFQJXRWWTBRXDS-OGNTWVNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.35
• 重原子数：
  25.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (E)-2-Oxo-dec-3-enoic acid (1S,2R)-2-phenyl-cyclohexyl ester 在 L-Selectride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 1.0h， 以90%的产率得到(E)-(S)-2-Hydroxy-dec-3-enoic acid (1S,2R)-2-phenyl-cyclohexyl ester
  参考文献：
  名称：

  Enantiospecific and diastereoselective synthesis of syn-β-amino-α-hydroxy acids

  摘要：

  The reaction of chiral alpha-hydroxy beta,gamma-unsaturated esters with tosyl isocyanate followed by cyclization of the resulting allylic carbamates with iodine in the presence of sodium carbonate provided trans-4,5-disubstituted 2-oxazolidinone derivatives in a highly diastereoselective manner. The subsequent removal of the iodo group and the protective functionality afforded the syn-beta-amino-alpha-hydroxy acids. Using the reaction sequence, (2R,3S)- and (2S,3R)-3-amino-2-hydroxy acids were synthesized with high enantioselectivity. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(97)00595-8
• 作为产物：
  描述：

  (1S,2R)-(+)-反-2-苯基-1-环己醇 、 2-oxo-decensaeureaethylester 在 正丁基锂 作用下， 生成 (E)-2-Oxo-dec-3-enoic acid (1S,2R)-2-phenyl-cyclohexyl ester
  参考文献：
  名称：

  Enantiospecific and diastereoselective synthesis of syn-β-amino-α-hydroxy acids

  摘要：

  The reaction of chiral alpha-hydroxy beta,gamma-unsaturated esters with tosyl isocyanate followed by cyclization of the resulting allylic carbamates with iodine in the presence of sodium carbonate provided trans-4,5-disubstituted 2-oxazolidinone derivatives in a highly diastereoselective manner. The subsequent removal of the iodo group and the protective functionality afforded the syn-beta-amino-alpha-hydroxy acids. Using the reaction sequence, (2R,3S)- and (2S,3R)-3-amino-2-hydroxy acids were synthesized with high enantioselectivity. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(97)00595-8