ethyl 2-bromo-5-methyl-2-hexenoate | 856350-81-7

• 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 2-bromo-5-methyl-2-hexenoate
• 英文别名: Ethyl 2-bromo-5-methylhex-2-enoate；ethyl 2-bromo-5-methylhex-2-enoate
• CAS: 856350-81-7
• 化学式: C₉H₁₅BrO₂
• 分子量: 235.121
• InChiKey: FKMVNDNQTGKHFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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 2-bromo-5-methyl-2-hexenoate 在 烟酰胺腺嘌呤双核苷酸磷酸盐 作用下， 以 乙醇 、 异丙醇 为溶剂， 反应 112.0h， 生成 (S)-3-氰基-5-甲基己酸乙酯
  参考文献：
  名称：

  Evaluation of Several Routes to Advanced Pregabalin Intermediates: Synthesis and Enantioselective Enzymatic Reduction Using Ene-Reductases

  摘要：

  This publication describes the evaluation of four synthetic routes to the advanced pregabalin (Lyrica) intermediate 7. Asymmetric reduction of (E)-7 with an ene-reductase (OPR1 from Lycopersicon esculentum) gave a saturated cyanoester intermediate 5 with the desired S stereocenter in >99% ee. OPR1 also catalyzed the reduction of (Z)-7 to (S)-5, but with lower conversion and selectivity.

  DOI：

  10.1021/op4002774

文献信息

• [EN] PROCESS FOR THE PREPARATION OF ( S ) - 3 - CYANO - 5 - METHYLHEXANOIC ACID DERIVATIVES ADN OF PREGABALIN<br/>[FR] PROCÉDÉ DE PRÉPARATION DE DÉRIVÉS D'ACIDE (S)-3-CYANO-5-MÉTHYLHEXANOÏQUE ET DE PRÉGABALINE
  申请人：PFIZER MFG IRELAND

  公开号：WO2012025861A1

  公开（公告）日：2012-03-01

  The invention provides a process for the manufacture of a compound of formula (I) using an enzyme catalysed reduction of a compound of formula (lla) or llb). Compounds of formula (I) are useful for preparing pregabalin.

  这项发明提供了一种利用酶催化还原公式(I)化合物的制备过程，其中所述化合物为公式(lla)或llb)的化合物。公式(I)的化合物可用于制备普拉巴林。
• Evaluation of Several Routes to Advanced Pregabalin Intermediates: Synthesis and Enantioselective Enzymatic Reduction Using Ene-Reductases
  作者：Sébastien Debarge、Paul McDaid、Pat O’Neill、James Frahill、John W. Wong、Donncha Carr、Adam Burrell、Simon Davies、Mike Karmilowicz、Jeremy Steflik

  DOI：10.1021/op4002774

  日期：2014.1.17

  This publication describes the evaluation of four synthetic routes to the advanced pregabalin (Lyrica) intermediate 7. Asymmetric reduction of (E)-7 with an ene-reductase (OPR1 from Lycopersicon esculentum) gave a saturated cyanoester intermediate 5 with the desired S stereocenter in >99% ee. OPR1 also catalyzed the reduction of (Z)-7 to (S)-5, but with lower conversion and selectivity.