methyl (2E)-2-(4-bromophenyl)-2-[tert-butyl(dimethyl)silyl]oxyiminoacetate | 1408233-65-7

• 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: methyl (2E)-2-(4-bromophenyl)-2-[tert-butyl(dimethyl)silyl]oxyiminoacetate
• CAS: 1408233-65-7
• 化学式: C₁₅H₂₂BrNO₃Si
• 分子量: 372.334
• InChiKey: UGZVSRQZDDICRP-GHRIWEEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.35
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  47.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (2E)-2-(4-bromophenyl)-2-[tert-butyl(dimethyl)silyl]oxyiminoacetate 、 己基溴化镁 以 四氢呋喃 为溶剂， 反应 0.25h， 以88%的产率得到N,N-dihexyl-2-(4-bromophenyl)glycine methyl ester
  参考文献：
  名称：

  Double nucleophilic N-alkylation of α-oxime-esters with Grignard reagents

  摘要：

  Double nucleophilic N-alkylation of alpha-oxime-esters, affording N,N-dialkyl-alpha-amino acids is herein described. Grignard reagents accomplished double N-alkylations via umpolung and various N.N-dialkylated alpha-amino acids were successfully synthesized in 15 min. Both electron-withdrawing sulfonyl groups and electron-donating silyl and methyl groups on oximes were available. Alkylmagnesium species and (E)-configuration of alpha-oxime-ester were essential to this cascade reaction. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.08.091
• 作为产物：
  描述：

  2-(4-溴苯基)-2-氧代乙酸甲酯 在 盐酸羟胺 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 9.0h， 生成 methyl (2E)-2-(4-bromophenyl)-2-[tert-butyl(dimethyl)silyl]oxyiminoacetate
  参考文献：
  名称：

  Double nucleophilic N-alkylation of α-oxime-esters with Grignard reagents

  摘要：

  Double nucleophilic N-alkylation of alpha-oxime-esters, affording N,N-dialkyl-alpha-amino acids is herein described. Grignard reagents accomplished double N-alkylations via umpolung and various N.N-dialkylated alpha-amino acids were successfully synthesized in 15 min. Both electron-withdrawing sulfonyl groups and electron-donating silyl and methyl groups on oximes were available. Alkylmagnesium species and (E)-configuration of alpha-oxime-ester were essential to this cascade reaction. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.08.091

文献信息

• Double nucleophilic N-alkylation of α-oxime-esters with Grignard reagents
  作者：Yusuke Mizutani、Hiroki Tanimoto、Tsumoru Morimoto、Yasuhiro Nishiyama、Kiyomi Kakiuchi

  DOI：10.1016/j.tetlet.2012.08.091

  日期：2012.10

  Double nucleophilic N-alkylation of alpha-oxime-esters, affording N,N-dialkyl-alpha-amino acids is herein described. Grignard reagents accomplished double N-alkylations via umpolung and various N.N-dialkylated alpha-amino acids were successfully synthesized in 15 min. Both electron-withdrawing sulfonyl groups and electron-donating silyl and methyl groups on oximes were available. Alkylmagnesium species and (E)-configuration of alpha-oxime-ester were essential to this cascade reaction. (C) 2012 Elsevier Ltd. All rights reserved.