ethyl (R)-3-acetamido-5-methyl-oct-2-enoate | 1337461-65-0

• 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 (R)-3-acetamido-5-methyl-oct-2-enoate
• 英文别名: ethyl (5R)-3-acetamido-5-methyloct-2-enoate
• CAS: 1337461-65-0
• 化学式: C₁₃H₂₃NO₃
• 分子量: 241.331
• InChiKey: GPGUTIMVUNTDTG-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.69
• 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：

  ethyl (R)-3-acetamido-5-methyl-oct-2-enoate 在 (+)-(R)-(tert-butylmethylphosphino-di-tert-butylphosphinomethane)-(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate 、 氢气 作用下， 以 甲醇 、 异辛烷 、 乙醇 为溶剂， 45.0~55.0 ℃ 、50.0 kPa 条件下， 反应 12.0h， 生成 (3S,5R)-3-acetylamino-5-methyl-octanoic acid ethyl ester
  参考文献：
  名称：

  The Development of a Practical Multikilogram Synthesis of the Chiral β-Amino Acid Imagabalin Hydrochloride (PD-0332334) via Asymmetric Hydrogenation

  摘要：

  The development and implementation of a robust process for the manufacture of metric ton quantities of the alpha 2 delta ligand imagabalin hydrochloride 4 is described. Key aspects of the synthesis include a chromatography-free, two-step telescoped process to prepare a mixture of Z:E-enamides 7 followed by a robust asymmetric hydrogenation with the rhodium-trichickenfootphos catalyst 8 to install the (3S)-stereocentre. Hydrolysis of the acetarnide and ester protecting groups in the final step followed by isolation and recrystallisation of the hydrochloride salt gave high purity 4 in 40-50% overall yields.

  DOI：

  10.1021/op2001639

文献信息

• PREPARATION OF BETA-AMINO ACIDS HAVING AFFINITY FOR THE ALPHA-2-DELTA PROTEIN
  申请人：Conway Brian G

  公开号：US20090247743A1

  公开（公告）日：2009-10-01

  Disclosed are materials and methods for preparing optically active β-amino acids of Formula 1, which bind to the alpha-2-delta (α2δ) subunit of a calcium channel.

  本发明涉及制备配方1的光学活性β-氨基酸的材料和方法，该配方1结合到钙通道的α2δ亚单位。
• [EN] PREPARATION OF BETA-AMINO ACIDS HAVING AFFINITY FOR THE ALPHA-2-DELTA PROTEIN<br/>[FR] PREPARATION DE BETA-AMINOACIDES AYANT UNE AFFINITE POUR LA PROTEINE ALPHA-2-DELTA
  申请人：WARNER LAMBERT CO

  公开号：WO2006008612A2

  公开（公告）日：2006-01-26

  Disclosed are materials and methods for preparing optically active ß-amino acids of Formula (1), which bind to the alpha-2-delta (α2δ) subunit of a calcium channel.