methyl (5R)-3-cyano-5-methyloctanoate | 1338784-17-0

• 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: methyl (5R)-3-cyano-5-methyloctanoate
• 英文别名: (5R)-3-cyano-5-methyl octanoic acid methyl ester
• CAS: 1338784-17-0
• 化学式: C₁₁H₁₉NO₂
• 分子量: 197.277
• InChiKey: BZPGKAYFCGJHNX-YHMJZVADSA-N

物化性质

• 沸点：
  293.1±23.0 °C(Predicted)
• 密度：
  0.949±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (5R)-3-cyano-5-methyloctanoate 在 Amano lipase PS-SD 、 水 、 碳酸氢钠 、 sodium hydroxide 作用下， 以 甲基叔丁基醚 、 水 、 甲苯 为溶剂， 25.0~45.0 ℃ 、344.75 kPa 条件下， 反应 2.0h， 生成 (3S,5R)-3-aminomethyl-5-methyl-octanoic acid
  参考文献：
  名称：

  Chemical Development of an α2δ Ligand, (3S,5R)-3-(Aminomethyl)-5-methyloctanoic Acid

  摘要：

  Three synthetic approaches, suitable for the large scale manufacture of the alpha 2 delta-ligand, (3S,5R)-3-(aminomethyl)-5-methyloctanoic acid 3, have been evaluated. The selected seven step manufacturing process has then been optimized and used to deliver over 20 kg of API; salient features of the synthesis include the use of 4,4,4-trimethoxybutyronitrile as an efficient four carbon amino acid equivalent. Highly selective kinetic resolution of the C3 stereocente was accomplished via diastereoselective hydrolysis of a cyanoester intermediate using Amano Lipase PS-SD. Extensive process optimisation of the route starting from (R)-2-methylpentanol, led to significant improvements through telescoping, with less than 62 kg of solvent being needed to produce 1 kg of API.

  DOI：

  10.1021/op2001832
• 作为产物：
  描述：

  2-甲基-1-戊醇 在 Amano lipase PS-C₁ 、 potassium tert-butylate 、 四丁基溴化铵 、 三乙胺 、 sodium bromide 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲基叔丁基醚 、 水 、 甲苯 为溶剂， 反应 19.0h， 生成 methyl (5R)-3-cyano-5-methyloctanoate
  参考文献：
  名称：

  Chemical Development of an α2δ Ligand, (3S,5R)-3-(Aminomethyl)-5-methyloctanoic Acid

  摘要：

  Three synthetic approaches, suitable for the large scale manufacture of the alpha 2 delta-ligand, (3S,5R)-3-(aminomethyl)-5-methyloctanoic acid 3, have been evaluated. The selected seven step manufacturing process has then been optimized and used to deliver over 20 kg of API; salient features of the synthesis include the use of 4,4,4-trimethoxybutyronitrile as an efficient four carbon amino acid equivalent. Highly selective kinetic resolution of the C3 stereocente was accomplished via diastereoselective hydrolysis of a cyanoester intermediate using Amano Lipase PS-SD. Extensive process optimisation of the route starting from (R)-2-methylpentanol, led to significant improvements through telescoping, with less than 62 kg of solvent being needed to produce 1 kg of API.

  DOI：

  10.1021/op2001832

文献信息

• Preparation of Gamma-Amino Acids Having Affinity for The Alpha-2-Delta Protein
  申请人：Evans Margaret Claire

  公开号：US20090299093A1

  公开（公告）日：2009-12-03

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

  本发明涉及一种制备结合到钙通道的α2δ亚基的光学活性γ-氨基酸的材料和方法，其化学式为1。
• Preparation of gamma-amino acids having affinity for the alpha-2-delta protein
  申请人：Pfizer Products Inc.

  公开号：EP2017259A2

  公开（公告）日：2009-01-21

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

  本发明公开了制备式 1 光学活性 γ 氨基酸的材料和方法、 与钙通道的α-2-δ（α2δ）亚基结合的材料和方法。
• PREPARATION OF GAMMA-AMINO ACIDS HAVING AFFINITY FOR THE ALPHA-2-DELTA PROTEIN
  申请人：Pfizer Products Inc.

  公开号：EP1973867A1

  公开（公告）日：2008-10-01
• [EN] PREPARATION OF GAMMA-AMINO ACIDS HAVING AFFINITY FOR THE ALPHA-2-DELTA PROTEIN<br/>[FR] PREPARATION D'ACIDES GAMMA-AMINES AYANT UNE AFFINITE POUR LA PROTEINE ALPHA-2-DELTA
  申请人：PFIZER PROD INC

  公开号：WO2007072159A1

  公开（公告）日：2007-06-28

  [EN] Disclosed are materials and methods for preparing optically active ?-amino acids of Formula (I), which bind to the alpha-2-delta (a2d) subunit of a calcium channel.
  [FR] La présente invention concerne des matériaux et procédés destinés à préparer des acides ?-aminés optiquement actifs répondant à la formule (I), qui se lient à la sous-unité alpha-2-delta (a2d) d'un canal calcique.
• Chemical Development of an α2δ Ligand, (3<i>S</i>,5<i>R</i>)-3-(Aminomethyl)-5-methyloctanoic Acid
  作者：Lorraine Murtagh、Catherine Dunne、Gino Gabellone、Niamh J. Panesar、Stuart Field、Lisa M. Reeder、James Saenz、George P. Smith、Kyle Kissick、Carlos, Martinez、John G. Van Alsten、Margaret C. Evans、Lloyd C. Franklin、Thomas Nanninga、John Wong

  DOI：10.1021/op2001832

  日期：2011.11.18

  Three synthetic approaches, suitable for the large scale manufacture of the alpha 2 delta-ligand, (3S,5R)-3-(aminomethyl)-5-methyloctanoic acid 3, have been evaluated. The selected seven step manufacturing process has then been optimized and used to deliver over 20 kg of API; salient features of the synthesis include the use of 4,4,4-trimethoxybutyronitrile as an efficient four carbon amino acid equivalent. Highly selective kinetic resolution of the C3 stereocente was accomplished via diastereoselective hydrolysis of a cyanoester intermediate using Amano Lipase PS-SD. Extensive process optimisation of the route starting from (R)-2-methylpentanol, led to significant improvements through telescoping, with less than 62 kg of solvent being needed to produce 1 kg of API.