(-)-N-(2'R)-methylbutyl-(2R)-methylbutylamide

• 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: (-)-N-(2'R)-methylbutyl-(2R)-methylbutylamide
• 英文别名: (2R)-2-methyl-N-[(2R)-2-methylbutyl]butanamide
• 化学式: C₁₀H₂₁NO
• 分子量: 171.283
• InChiKey: RJTQFUOHMKVLEG-RKDXNWHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (S)-2-甲基丁酰氯 在 吡啶 、 ammonium hydroxide 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 6.5h， 生成 (-)-N-(2'R)-methylbutyl-(2R)-methylbutylamide
  参考文献：
  名称：

  长角甲虫的性信息素N-2'-甲基丁基-2-甲基丁基酰胺的四种可能立体异构体的合成

  摘要：

  合成了N-2'-甲基丁基-2-甲基丁基酰胺的四种立体异构体，它是南美洲重要的甘蔗害虫Migdolus furyanus 的性信息素。关键中间体 2-methylbutan-1-ol 仅以其 (S)-(-)-形式在市场上销售。(R)-(+)-对映异构体分五步从(S)-(+)-3-羟基-2-甲基丙酸甲酯获得光学纯的。

  DOI：

  10.1081/scc-100107019

文献信息

• PROCESS FOR PREPARING 2-METHYL-N- (2' -METHYLBUTYL) BUTANAMIDE
  申请人：Shin-Etsu Chemical Co., Ltd.

  公开号：EP4101840A1

  公开（公告）日：2022-12-14

  The present invention provides a process for preparing 2-methyl-N-(2'-methylbutyl)butanamide of the following formula (1):the process comprising: subjecting an α-arylethyl-2-methylbutylamine compound of the following general formula (2): wherein Ar represents a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, to N-2-methylbutyrylation to form an N-α-arylethyl-2-methyl-N-(2'-methylbutyl)butanamide compound of the following general formula (3): wherein Ar is as defined above, and removing the α-arylethyl group of the resulting compound (3) to form 2-methyl-N-(2'-methylbutyl)butanamide (1).

  本发明提供了一种制备下式(1)的2-甲基-N-(2'-甲基丁基)丁酰胺的工艺：该工艺包括：将下通式(2)的α-芳烯醇基-2-甲基丁胺化合物：其中 Ar 代表具有 6 至 20 个碳原子的取代或未取代的芳基，将其进行 N-2-甲基丁酰化，形成下式通式(3)的 N-α-芳烯丙基-2-甲基-N-(2'-甲基丁基)丁酰胺化合物： 其中 Ar 如上定义，并除去所得化合物(3)中的α-芳烯丙基，形成 2-甲基-N-(2'-甲基丁基)丁酰胺(1)。
• PROCESS FOR PREPARING 2-METHYL-N-(2' -METHYLBUTYL)BUTANAMIDE
  申请人：Shin-Etsu Chemical Co., Ltd.

  公开号：US20220411363A1

  公开（公告）日：2022-12-29

  The present invention provides a process for preparing 2-methyl-N-(2′-methylbutyl)butanamide of the following formula (1):the process comprising: subjecting an α-arylethyl-2-methylbutylamine compound of the following general formula (2): wherein Ar represents a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, to N-2-methylbutyrylation to form an N-α-arylethyl-2-methyl-N-(2′-methylbutyl)butanamide compound of the following general formula (3): wherein Ar is as defined above, and removing the α-arylethyl group of the resulting compound (3) to form 2-methyl-N-(2′-methylbutyl)butanamide (1).
• SYNTHESIS OF THE FOUR POSSIBLE STEREOISOMERS OF<i>N</i>-2′-METHYLBUTYL-2-METHYLBUTYLAMIDE, THE SEX PHEROMONE OF THE LONGHORN BEETLE<i>MIGDOLUS FRYANUS</i>WESTWOOD
  作者：Ellen M. Santangelo、Paulo H. G. Zarbin、Quezia B. Cass、José T. B. Ferreira、Arlene G. Corrêa

  DOI：10.1081/scc-100107019

  日期：2001.1

  four stereoisomers of N-2′-methylbutyl-2-methylbutylamide, the sex pheromone of the longhorn beetle Migdolus fryanus, an economically important pest of sugarcane in South America, were synthesized. The key intermediate 2-methylbutan-1-ol is commercially available only in its (S)-(−)-form. The (R)-(+)-enantiomer was obtained optically pure from methyl (S)-(+)-3-hydroxy-2-methylpropionate in five steps

  合成了N-2'-甲基丁基-2-甲基丁基酰胺的四种立体异构体，它是南美洲重要的甘蔗害虫Migdolus furyanus 的性信息素。关键中间体 2-methylbutan-1-ol 仅以其 (S)-(-)-形式在市场上销售。(R)-(+)-对映异构体分五步从(S)-(+)-3-羟基-2-甲基丙酸甲酯获得光学纯的。