2-Chloro-N,N-diethyl-3-hydroxy-2,3-dimethyl-4-phenylbutanamide | 368425-52-9

• 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: 2-Chloro-N,N-diethyl-3-hydroxy-2,3-dimethyl-4-phenylbutanamide
• CAS: 368425-52-9
• 化学式: C₁₆H₂₄ClNO₂
• 分子量: 297.825
• InChiKey: JFJBLMAQWWOLBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 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：

  2-Chloro-N,N-diethyl-3-hydroxy-2,3-dimethyl-4-phenylbutanamide 在 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 生成 (Z)-N,N-Diethyl-2,3-dimethyl-2,3-dimethyl-4-phenylbut-2-enamide 、 (E)-N,N-Diethyl-2,3-dimethyl-2,3-dimethyl-4-phenylbut-2-enamide
  参考文献：
  名称：

  Synthesis of (E)-α,β-Unsaturated Amides with High Selectivity by Using Samarium Diiodide

  摘要：

  Stereoselective beta -elimination of 2-chloro-3-hydroxyamides 1 is achieved by using samarium diiodide to yield alpha,beta -unsaturated amides 2, in which the C=C bond is di- tri-, or tetrasubstituted. The starting compounds a are easily prepared by reaction of the corresponding lithium enolates of alpha -chloroamides with aldehydes or ketones at -78 degreesC. The influence of the reaction conditions and the structure of the starting compounds on the stereoselectivity of the beta -elimination reaction is also discussed.

  DOI：

  10.1002/1521-3765(20010716)7:14<3062::aid-chem3062>3.0.co;2-f
• 作为产物：
  描述：

  N,N-二乙基-2-氯丙酰胺 、 苯基丙酮 在 lithium diisopropyl amide 作用下， 生成 2-Chloro-N,N-diethyl-3-hydroxy-2,3-dimethyl-4-phenylbutanamide
  参考文献：
  名称：

  Sequential Elimination−Cyclopropanation Reactions Promoted by Samarium:  Highly Diastereoselective Synthesis of Cyclopropylamides

  摘要：

  trans-Cyclopropanamides were obtained, in high yield, from 2-chloro-3-hydroxyamides by a sequenced elimination-cyclopropanation process promoted by Samarium/diiodomethane or Samarium diiodide and Samarium/diiodomethane.

  DOI：

  10.1021/jo0262098