ethyl (4S)-4-cyano-4-phenyl-5-methylhexanoate | 318969-12-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl (4S)-4-cyano-4-phenyl-5-methylhexanoate
• 英文别名: ethyl (4S)-4-cyano-5-methyl-4-phenylhexanoate
• CAS: 318969-12-9
• 化学式: C₁₆H₂₁NO₂
• 分子量: 259.348
• InChiKey: KJNTXYMUWPPJPC-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  ethyl (4S)-4-cyano-4-phenyl-5-methylhexanoate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以97%的产率得到(2S)-2-(2-isopropyl)-5-hydroxy-2-phenylpentanenitrile
  参考文献：
  名称：

  Practical Synthesis of Chiral Emopamil Left Hand as a Bioactive Motif

  摘要：

  An asymmetric synthesis of (2S)-2-(2-isopropyl)-5-hydroxy-2-phenylpentanenitrile (emopamil left hand, 2) has been completed by use of the MAD (methyl aluminum bis(4-methyl-2,6-di-tert-butylphenoxide)-induced rearrangement of a chiral epoxyalcohol as the key reaction. The stereochemistry of the chiral quaternary center was confirmed by transformation of 2 to (S)-noremopamil. This method requires minimal purification procedures and affords high chemical and optical yields. Acid-catalyzed isomerization of an allylaldehyde and retro-aldol type racemization at the quaternary carbon of a nitrile-alcohol were encountered.

  DOI：

  10.1021/jo020166d
• 作为产物：
  描述：

  (2S,3S)-3-isopropyl-2-phenyl-2,3-epoxypropan-1-triphenylsilyl ether 在 palladium on activated charcoal pyridine-SO3 complex 、 盐酸羟胺 、 四丁基氟化铵 、 氢气 、 sodium acetate 、 甲铝双(2,6-二叔丁基-4-苯甲醚) 、 sodium hydride 、 三乙胺 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 二甲基亚砜 、 乙酸乙酯 、 甲苯 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 28.0h， 生成 ethyl (4S)-4-cyano-4-phenyl-5-methylhexanoate
  参考文献：
  名称：

  Practical Synthesis of Chiral Emopamil Left Hand as a Bioactive Motif

  摘要：

  An asymmetric synthesis of (2S)-2-(2-isopropyl)-5-hydroxy-2-phenylpentanenitrile (emopamil left hand, 2) has been completed by use of the MAD (methyl aluminum bis(4-methyl-2,6-di-tert-butylphenoxide)-induced rearrangement of a chiral epoxyalcohol as the key reaction. The stereochemistry of the chiral quaternary center was confirmed by transformation of 2 to (S)-noremopamil. This method requires minimal purification procedures and affords high chemical and optical yields. Acid-catalyzed isomerization of an allylaldehyde and retro-aldol type racemization at the quaternary carbon of a nitrile-alcohol were encountered.

  DOI：

  10.1021/jo020166d

文献信息

• Practical Synthesis of Chiral Emopamil Left Hand as a Bioactive Motif
  作者：Teiji Kimura、Noboru Yamamoto、Yuichi Suzuki、Koki Kawano、Yoshihiko Norimine、Koichi Ito、Satoshi Nagato、Yoichi Iimura、Masahiro Yonaga

  DOI：10.1021/jo020166d

  日期：2002.8.1

  An asymmetric synthesis of (2S)-2-(2-isopropyl)-5-hydroxy-2-phenylpentanenitrile (emopamil left hand, 2) has been completed by use of the MAD (methyl aluminum bis(4-methyl-2,6-di-tert-butylphenoxide)-induced rearrangement of a chiral epoxyalcohol as the key reaction. The stereochemistry of the chiral quaternary center was confirmed by transformation of 2 to (S)-noremopamil. This method requires minimal purification procedures and affords high chemical and optical yields. Acid-catalyzed isomerization of an allylaldehyde and retro-aldol type racemization at the quaternary carbon of a nitrile-alcohol were encountered.