(R)-N-Benzyl-N-methyl-3-hydroxy-4-pentenamide | 151379-77-0

• 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: (R)-N-Benzyl-N-methyl-3-hydroxy-4-pentenamide
• 英文别名: N-benzyl-N-methyl-3-hydroxy-4-pentenamide；(3R)-N-benzyl-3-hydroxy-N-methylpent-4-enamide
• CAS: 151379-77-0
• 化学式: C₁₃H₁₇NO₂
• 分子量: 219.283
• InChiKey: DADDQYSOCCJWBS-LBPRGKRZSA-N

物化性质

• 沸点：
  380.4±42.0 °C(predicted)
• 密度：
  1.084±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-N-Benzyl-N-methyl-3-hydroxy-4-pentenamide 在 咪唑 、 4-二甲氨基吡啶 、 偶氮二异丁腈 、 碘 、 三正丁基氢锡 、 间氯过氧苯甲酸 、 三苯基膦 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 、 苯 为溶剂， 反应 50.0h， 生成 (3R,4S)-3-<(tert-Butyldimethylsilyl)oxy>-4-methyl-γ-butyrolactone
  参考文献：
  名称：

  New Synthesis of All Four Isomers of 3-Hydroxy-4-methyl-.gamma.-butyrolactone by Stereoselective Intramolecular Lactonization. Application to Asymmetric Synthesis of Biologically Active Compounds

  摘要：

  A new synthesis of all four isomeric 3-hydroxy-4-methyl-gamma-butyrolactones (11, ent-11, 12, ent-12) has been performed. The former two were prepared via stereoselective iodolactonization, which favors the cis-3,4-disubstituted system (16a and ent-16a), of N-benzyl-N-methyl-3-hydroxy-4-pentenamides (R)- and (S)-13, readily available by resolution of the racemate by lipase-mediated transesterification; and the latter two were prepared via stereoselective oxylactonization, which favors the trans-3,4-disubstituted system [(3R,4S)-20a and ent-(3R,4S)-20a], of O-TBDMS-protected N-benzyl-N-methyl-3-hydroxy-4-pentenamides (R)- and (S)-14. Butyrolactones 11 and 12 have been readily transformed into biologically active compounds [(-)-blastmycinolactol (27), (-)-NFX-2 (2), (-)-NFX-4 (3), lipid metabolites 9 and 10, and the sex pheromone (-)-(2S,3S)-2,3-octanediol (30)].

  DOI：

  10.1021/jo00103a008
• 作为产物：
  描述：

  N-Benzyl-N-methyl-3-hydroxy-4-pentenamide 生成 (R)-N-Benzyl-N-methyl-3-hydroxy-4-pentenamide
  参考文献：
  名称：

  Enzymatic resolution of N,N-dialkyl-3-hydroxy-4-pentenamides, unsuccessful in resolution by the Katsuki-Sharpless asymmetric epoxidation

  摘要：

  An immobilized lipase-mediated resolution of secondary allylic alcohols 1 and 2 with which the Katsuki-Sharpless asymmetric epoxidation is unsuccessful is described.

  DOI：

  10.1016/s0957-4166(00)80150-0

文献信息

• New entry to chiral butenolide synthons. Application to expeditious syntheses of (+)-nephrosteranic acid, (+)-trans-whisky lactone, and (+)-trans-cognac lactone
  作者：Hiroki Takahata、Yasuhiro Uchida、Takefumi Momose

  DOI：10.1016/s0040-4039(00)73129-7

  日期：1994.6

  A new envy to chiral butenolide synthons starting with iodolactonization of the readily available, homochiral N-benzyl-N-methyl-3-hydroxy-4-pentenamid (1) and its application to the syntheses of (+)-nephrosteranic acid (5), (+)-trans-whisky lactone (6), and (+)-trans-cognac lactone (7) are described.
• New Synthesis of All Four Isomers of 3-Hydroxy-4-methyl-.gamma.-butyrolactone by Stereoselective Intramolecular Lactonization. Application to Asymmetric Synthesis of Biologically Active Compounds
  作者：Hiroki Takahata、Yasuhiro Uchida、Takefumi Momose

  DOI：10.1021/jo00103a008

  日期：1994.12

  A new synthesis of all four isomeric 3-hydroxy-4-methyl-gamma-butyrolactones (11, ent-11, 12, ent-12) has been performed. The former two were prepared via stereoselective iodolactonization, which favors the cis-3,4-disubstituted system (16a and ent-16a), of N-benzyl-N-methyl-3-hydroxy-4-pentenamides (R)- and (S)-13, readily available by resolution of the racemate by lipase-mediated transesterification; and the latter two were prepared via stereoselective oxylactonization, which favors the trans-3,4-disubstituted system [(3R,4S)-20a and ent-(3R,4S)-20a], of O-TBDMS-protected N-benzyl-N-methyl-3-hydroxy-4-pentenamides (R)- and (S)-14. Butyrolactones 11 and 12 have been readily transformed into biologically active compounds [(-)-blastmycinolactol (27), (-)-NFX-2 (2), (-)-NFX-4 (3), lipid metabolites 9 and 10, and the sex pheromone (-)-(2S,3S)-2,3-octanediol (30)].
• Enzymatic resolution of N,N-dialkyl-3-hydroxy-4-pentenamides, unsuccessful in resolution by the Katsuki-Sharpless asymmetric epoxidation
  作者：Hiroki Takahata、Yasuhiro Uchida、Yoshie Ohkawa、Takefumi Momose

  DOI：10.1016/s0957-4166(00)80150-0

  日期：1993.5

  An immobilized lipase-mediated resolution of secondary allylic alcohols 1 and 2 with which the Katsuki-Sharpless asymmetric epoxidation is unsuccessful is described.