2-Methyl-propane-2-sulfinic acid [(R)-1-isopropyl-3-methyl-5-oxo-5-phenyl-pent-(Z)-ylidene]-amide | 865993-99-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Methyl-propane-2-sulfinic acid [(R)-1-isopropyl-3-methyl-5-oxo-5-phenyl-pent-(Z)-ylidene]-amide
• 英文别名: (NZ,R)-N-[(5R)-2,5-dimethyl-7-oxo-7-phenylheptan-3-ylidene]-2-methylpropane-2-sulfinamide
• CAS: 865993-99-3
• 化学式: C₁₉H₂₉NO₂S
• 分子量: 335.511
• InChiKey: PUPYVXJDOAZOJX-KPKHEABGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  65.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-Methyl-propane-2-sulfinic acid [(R)-1-isopropyl-3-methyl-5-oxo-5-phenyl-pent-(Z)-ylidene]-amide 在 L-Selectride 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 2.0h， 生成 2-Methyl-propane-2-sulfinic acid ((1S,3S)-1-isopropyl-3-methyl-5-oxo-5-phenyl-pentyl)-amide
  参考文献：
  名称：

  N-Sulfinyl Metalloenamine Conjugate Additions:  Asymmetric Synthesis of Piperidines

  摘要：

  [GRAPHICS]The first examples of conjugate additions of N-tert-butanesulfinyl metalloenamines are reported. Highly stereoselective conjugate additions (97:3 to 99:1 dr) were observed between metalloenamines derived from N-sulfinyl ketimines and alpha,beta-unsaturated ketones bearing either alkyl or aryl substituents. The conjugate addition products could rapidly be converted with high diastereoselectivity to 2,4,6-trisubstituted piperidines, which are difficult to access by other methods.

  DOI：

  10.1021/jo051020s
• 作为产物：
  描述：

  反式-1-苯基-2-丁烯-1-酮 、 (R)-(-)-N-(3-methyl-2-butylidene)-2-methylpropanesulfinamide 在 正丁基锂 、 二异丙胺 、 zinc dibromide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 5.75h， 以72%的产率得到2-Methyl-propane-2-sulfinic acid [(R)-1-isopropyl-3-methyl-5-oxo-5-phenyl-pent-(Z)-ylidene]-amide
  参考文献：
  名称：

  N-Sulfinyl Metalloenamine Conjugate Additions:  Asymmetric Synthesis of Piperidines

  摘要：

  [GRAPHICS]The first examples of conjugate additions of N-tert-butanesulfinyl metalloenamines are reported. Highly stereoselective conjugate additions (97:3 to 99:1 dr) were observed between metalloenamines derived from N-sulfinyl ketimines and alpha,beta-unsaturated ketones bearing either alkyl or aryl substituents. The conjugate addition products could rapidly be converted with high diastereoselectivity to 2,4,6-trisubstituted piperidines, which are difficult to access by other methods.

  DOI：

  10.1021/jo051020s

文献信息

• <i>N</i>-Sulfinyl Metalloenamine Conjugate Additions:  Asymmetric Synthesis of Piperidines
  作者：Hillary M. Peltier、Jonathan A. Ellman

  DOI：10.1021/jo051020s

  日期：2005.9.1

  [GRAPHICS]The first examples of conjugate additions of N-tert-butanesulfinyl metalloenamines are reported. Highly stereoselective conjugate additions (97:3 to 99:1 dr) were observed between metalloenamines derived from N-sulfinyl ketimines and alpha,beta-unsaturated ketones bearing either alkyl or aryl substituents. The conjugate addition products could rapidly be converted with high diastereoselectivity to 2,4,6-trisubstituted piperidines, which are difficult to access by other methods.