ethyl (5R)-5-methyloct-2-enoate | 1337461-76-3

• 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: ethyl (5R)-5-methyloct-2-enoate
• CAS: 1337461-76-3
• 化学式: C₁₁H₂₀O₂
• 分子量: 184.279
• InChiKey: VJZVGQOYXUSDPG-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl (5R)-5-methyloct-2-enoate 、 (S)-(-)-N-苄基-1-苯基-乙胺 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以92%的产率得到ethyl (3S,5R)-3-[benzyl-[(1S)-1-phenylethyl]amino]-5-methyloctanoate
  参考文献：
  名称：

  Diastereoselective, large-scale synthesis of β-amino acids via asymmetric aza-Michael addition as α2δ ligands for the treatment of generalized anxiety disorder and insomnia

  摘要：

  Scalable synthetic routes to beta-amino acids 1 and 2 are presented. These two compounds, which bind to the alpha 2 delta subunit of calcium channels and have important medical applications, have been prepared on kilogram scale in our pilot plant through an improved synthesis that avoids the use of highly toxic reagents and hazardous chemistry present in the original Medicinal Chemistry route. The two chiral centers are introduced through asymmetric Michael and aza-Michael reactions with excellent diastereoselectivity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.08.119
• 作为产物：
  描述：

  ethyl (5R)-5-methyl-3-methylsulfonyloxyoctanoate 在 三乙胺 作用下， 以 乙酸乙酯 为溶剂， 生成 ethyl (5R)-5-methyloct-2-enoate
  参考文献：
  名称：

  Diastereoselective, large-scale synthesis of β-amino acids via asymmetric aza-Michael addition as α2δ ligands for the treatment of generalized anxiety disorder and insomnia

  摘要：

  Scalable synthetic routes to beta-amino acids 1 and 2 are presented. These two compounds, which bind to the alpha 2 delta subunit of calcium channels and have important medical applications, have been prepared on kilogram scale in our pilot plant through an improved synthesis that avoids the use of highly toxic reagents and hazardous chemistry present in the original Medicinal Chemistry route. The two chiral centers are introduced through asymmetric Michael and aza-Michael reactions with excellent diastereoselectivity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.08.119

文献信息

• Diastereoselective, large-scale synthesis of β-amino acids via asymmetric aza-Michael addition as α2δ ligands for the treatment of generalized anxiety disorder and insomnia
  作者：Javier Magano、Daniel Bowles、Brian Conway、Thomas N. Nanninga、Derick D. Winkle

  DOI：10.1016/j.tetlet.2009.08.119

  日期：2009.11

  Scalable synthetic routes to beta-amino acids 1 and 2 are presented. These two compounds, which bind to the alpha 2 delta subunit of calcium channels and have important medical applications, have been prepared on kilogram scale in our pilot plant through an improved synthesis that avoids the use of highly toxic reagents and hazardous chemistry present in the original Medicinal Chemistry route. The two chiral centers are introduced through asymmetric Michael and aza-Michael reactions with excellent diastereoselectivity. (C) 2009 Elsevier Ltd. All rights reserved.