N-[(2R)-2-phenylpent-4-en-2-yl]acetamide | 131154-23-9

• 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: N-[(2R)-2-phenylpent-4-en-2-yl]acetamide
• CAS: 131154-23-9
• 化学式: C₁₃H₁₇NO
• 分子量: 203.284
• InChiKey: OVKLASDVMXGNAE-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-[(2R)-2-phenylpent-4-en-2-yl]acetamide 在 氢氧化钾 、 sodium hydroxide 、 硼烷四氢呋喃络合物 、 双氧水 、 silver nitrate 、 pyridinium chlorochromate 作用下， 反应 3.0h， 生成 (R)-4-Acetylamino-4-phenyl-pentanoic acid
  参考文献：
  名称：

  Stereoselective addition reactions of chiral N-benzylidene-p-toluenesulfinamides. Asymmetric syntheses of .beta.- and .gamma.-amino acids

  摘要：

  Chiral N-benzylidene-p-toluenesulfinamides 2 were prepared by the reaction of benzonitrile with alkyllithium in ether followed by (-)-l-menthyl (S)-p-tolylsulfinate. Treatment of 2 with allylmagnesium bromide in ether at 0-degrees-C gave the adducts (R)-7 with excellent stereoselectivity. Pure chiral sulfinamides 7 were converted into chiral beta- and gamma-amino acids in four and five steps, respectively.

  DOI：

  10.1021/jo00001a003
• 作为产物：
  描述：

  (NE,R)-4-methyl-N-(1-phenylethylidene)benzenesulfinamide 在 三乙胺 、 三氟乙酸 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 6.5h， 生成 N-[(2R)-2-phenylpent-4-en-2-yl]acetamide
  参考文献：
  名称：

  Stereoselective addition reactions of chiral N-benzylidene-p-toluenesulfinamides. Asymmetric syntheses of .beta.- and .gamma.-amino acids

  摘要：

  Chiral N-benzylidene-p-toluenesulfinamides 2 were prepared by the reaction of benzonitrile with alkyllithium in ether followed by (-)-l-menthyl (S)-p-tolylsulfinate. Treatment of 2 with allylmagnesium bromide in ether at 0-degrees-C gave the adducts (R)-7 with excellent stereoselectivity. Pure chiral sulfinamides 7 were converted into chiral beta- and gamma-amino acids in four and five steps, respectively.

  DOI：

  10.1021/jo00001a003

文献信息

• Copper-catalyzed asymmetric allylation of chiral N-tert-butanesulfinyl imines: dual stereocontrol with nearly perfect diastereoselectivity
  作者：Yi-Shuang Zhao、Qiang Liu、Ping Tian、Jing-Chao Tao、Guo-Qiang Lin

  DOI：10.1039/c5ob00322a

  日期：——

  Copper-catalyzed asymmetric allylation of chiral N-tert-butanesulfinyl imines has been described. Dual stereocontrol, through the combination of a chiral auxiliary and a chiral copper complex, has played an important role in achieving the nearly perfect diastereoselectivities (all dr > 99 : 1), especially for ketimine substrates.

  已经描述了铜催化的手性N-叔-丁烷亚磺酰基亚胺的不对称烯丙基化。通过手性助剂和手性铜配合物的结合，双重立体控制在实现近乎完美的非对映选择性（所有dr> 99：1）方面起着重要作用，尤其是对于酮亚胺底物。