2-cyano-5-methylhexaoic acid | 95658-25-6

• 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: 2-cyano-5-methylhexaoic acid
• 英文别名: 2-cyano-5-methyl-hexanoic acid；2-Cyan-5-methyl-hexansaeure；2-Cyano-5-methylhexanoic acid；2-cyano-5-methylhexanoic acid
• CAS: 95658-25-6
• 化学式: C₈H₁₃NO₂
• 分子量: 155.197
• InChiKey: LUBUODPHZAMXSV-UHFFFAOYSA-N

物化性质

• 熔点：
  47-48 °C
• 沸点：
  175-180 °C(Press: 16 Torr)
• 密度：
  1.039±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  61.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-cyano-5-methylhexaoic acid 、 L-薄荷醇 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以80%的产率得到(-)-menthyl 2-cyano-5-methylhexanoate
  参考文献：
  名称：

  Phosphoramidites Are Efficient, Green Organocatalysts for the Michael Reaction. Mechanistic Insights into the Phosphorus-Catalyzed Michael Reaction of Alkynones and Implications for Asymmetric Catalysis

  摘要：

  Hexamethylphosphorous triamide (HMPT) and other phosphoramidites and phosphites have been found to be efficient catalysts for the Michael reaction of alkenones and alkynones with malonates, (x-cyano, esters, beta-keto esters, and nitro compounds. The relatively nontoxic, easily hydrolyzed HMPT catalyzes the Michael reaction within seconds at room temperature in the absence of a solvent, and the reaction is worked up simply by removing the catalyst in vacuo. The Michael reactions of alkynones, unlike those of alkenones, are shown to be irreversible. The implications for asymmetric catalysis are discussed.

  DOI：

  10.1021/jo026425g
• 作为产物：
  描述：

  异戊基碘 、 氰乙酸乙酯 、 异戊醇钠 生成 2-cyano-5-methylhexaoic acid 、 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  ALKYL CYANO-ACETIC ESTERS.¹

  摘要：

  DOI：

  10.1021/ja01434a029

文献信息

• [EN] STEREOSELECTIVE ENZYMATIC SYNTHESIS OF (S) OR (R)-ISO-BUTYL-GLUTARIC ESTER<br/>[FR] SYNTHÈSE ENZYMATIQUE STÉRÉOSÉLECTIVE DE L'ESTER (S) OU (R)-ISOBUTYLGLUTARIQUE
  申请人：TEVA PHARMA

  公开号：WO2009158343A1

  公开（公告）日：2009-12-30

  The present invention relates to a stereoselective enzymatic synthesis of (S) or (R)-iso-butyl-glutaric ester, an intermediate of S-Pregabalin.

  本发明涉及(S)或(R)-异丁基戊二酸酯的立体选择性酶合成，该酯是S-Pregabalin的中间体。
• Stereoselective bioconversion of aliphatic dinitriles into cyano carboxylic acids
  申请人：Burns P. Michael

  公开号：US20070196905A1

  公开（公告）日：2007-08-23

  The present invention is directed to a regio- and stereoselective bioconversion of selected aliphatic dinitriles into corresponding cyanocarboxylic acids. More particularly, the present invention provides methods for the conversion of 2-isobutyl-succinonitrile into (S)-3 cyano-5-methylhexanoic acid, which is a useful intermediate in the synthesis of (S)-3(aminomethyl)-5-methylhexanoic acid (pregabalin). Pregabalin can be used for treating certain cerebral diseases, for example, in the treatment and prevention of seizure disorders, pain, and psychotic disorders.

  本发明涉及选择性的区域和立体选择性的生物转化，将特定的脂肪族二腈转化为相应的腈羧酸。更具体地，本发明提供将2-异丁基琥珀腈转化为(S)-3-氰基-5-甲基己酸的方法，该化合物是(S)-3(氨甲基)-5-甲基己酸（盐酸盐）（盐酸普瑞巴林）合成中的有用中间体。盐酸普瑞巴林可用于治疗某些脑部疾病，例如治疗和预防癫痫、疼痛和精神疾患。
• Preparation of (S)-pregabalin-nitrile
  申请人：Hedvati Lilach

  公开号：US20080015385A1

  公开（公告）日：2008-01-17

  Provided are processes for the preparation of (3S)-cyano-5-methylhexanoic acid, an intermediate in the synthesis of (S)-pregabalin.

  提供了制备(3S)-氰基-5-甲基己酸的过程，它是(S)-pregabalin合成中的中间体。
• STEREOSELECTIVE ENZYMATIC SYNTHESIS OF (S) OR (R)-ISO-BUTYL-GLUTARIC ESTER
  申请人：Hedvati Lilach

  公开号：US20100087525A1

  公开（公告）日：2010-04-08

  The present invention relates to a stereoselective enzymatic synthesis of (S) or (R)-iso-butyl-glutaric ester, an intermediate of S-Pregabalin.

  本发明涉及(S)或(R)-异丁基戊二酸酯的立体选择性酶催化合成，该化合物是S-Pregabalin的中间体。
• Stereoselective Bioconversion of Aliphatic Dinitriles into Cyano Carboxylic Acids
  申请人：Burns Michael P.

  公开号：US20100204503A1

  公开（公告）日：2010-08-12

  The present invention is directed to a regio- and stereoselective bioconversion of selected aliphatic dinitriles into corresponding cyanocarboxylic acids. More particularly, the present invention provides methods for the conversion of 2-isobutyl-succinonitrile into (S)-3 cyano-5-methylhexanoic acid, which is a useful intermediate in the synthesis of (S)-3(aminomethyl)-5-methylhexanoic acid (pregabalin). Pregabalin can be used for treating certain cerebral diseases, for example, in the treatment and prevention of seizure disorders, pain, and psychotic disorders.

  本发明涉及选择性的区域和立体选择性的生物转化方法，将特定的脂肪族双腈转化为相应的氰基羧酸。更具体地说，本发明提供将2-异丁基琥珀腈转化为（S）-3氰基-5-甲基己酸的方法，该中间体在合成（S）-3（氨甲基）-5-甲基己酸（盐酸普瑞巴林）时非常有用。盐酸普瑞巴林可用于治疗某些脑部疾病，例如治疗和预防癫痫、疼痛和精神障碍。