methyl 2-<(trimethylsilyl)methyl>amino-2-phenylacetate | 220437-96-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 2-<(trimethylsilyl)methyl>amino-2-phenylacetate
• 英文别名: Methyl 2-phenyl-2-(trimethylsilylmethylamino)acetate；methyl 2-phenyl-2-(trimethylsilylmethylamino)acetate
• CAS: 220437-96-7
• 化学式: C₁₃H₂₁NO₂Si
• 分子量: 251.401
• InChiKey: DVFWCJMWCPVOQB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.37
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 2-<(trimethylsilyl)methyl>amino-2-phenylacetate 在 lithium aluminium tetrahydride 、 potassium carbonate 、 cesium fluoride 作用下， 以 乙腈 为溶剂， 反应 26.0h， 生成 3-(二甲氨基)-3-苯基丙烷-1-醇
  参考文献：
  名称：

  Novel Isomerization Reaction of N,N-Dimethyl-α-(methoxycarbonyl)-4-substituted- benzylammonium N-Methylides

  摘要：

  Fluoride ion-induced desilylation of N,N-dimethyl-N-[(trimethylsilyl)methyl]-alpha-(methoxycarbonyl)- 4-substituted benzylammonium salts (7) gave two Stevens rearrangement products: methyl 3-(dimethylamino)-2-(4-substituted phenyl)propionates (13) from N-methylides 8, and methyl 3-(dimethylamino)-3-(4-substituted phenyl)propionates (15) from N-benzylides 10. Additional Stevens rearrangement products, methyl 2-(dimethylamino)-3-(4-substituted phenyl)propionates (16), were competitively formed from ylides 12 when the cesium fluoride used was not predried. The mechanism of the isomerization from methylides 8, which was initially generated, to 10 and 12 is discussed.

  DOI：

  10.1021/jo981729h
• 作为产物：
  描述：

  氯甲基三甲基硅烷 、 苯基甘氨酸甲酯盐酸盐 在 potassium carbonate 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以54%的产率得到methyl 2-<(trimethylsilyl)methyl>amino-2-phenylacetate
  参考文献：
  名称：

  Novel Isomerization Reaction of N,N-Dimethyl-α-(methoxycarbonyl)-4-substituted- benzylammonium N-Methylides

  摘要：

  Fluoride ion-induced desilylation of N,N-dimethyl-N-[(trimethylsilyl)methyl]-alpha-(methoxycarbonyl)- 4-substituted benzylammonium salts (7) gave two Stevens rearrangement products: methyl 3-(dimethylamino)-2-(4-substituted phenyl)propionates (13) from N-methylides 8, and methyl 3-(dimethylamino)-3-(4-substituted phenyl)propionates (15) from N-benzylides 10. Additional Stevens rearrangement products, methyl 2-(dimethylamino)-3-(4-substituted phenyl)propionates (16), were competitively formed from ylides 12 when the cesium fluoride used was not predried. The mechanism of the isomerization from methylides 8, which was initially generated, to 10 and 12 is discussed.

  DOI：

  10.1021/jo981729h

文献信息

• Novel Isomerization Reaction of <i>N</i>,<i>N</i>-Dimethyl-α-(methoxycarbonyl)-4-substituted- benzylammonium <i>N</i>-Methylides
  作者：Chen Zhang、Hiroto Ito、Yasuhiro Maeda、Naohiro Shirai、Shin-ichi Ikeda、Yoshiro Sato

  DOI：10.1021/jo981729h

  日期：1999.1.1

  Fluoride ion-induced desilylation of N,N-dimethyl-N-[(trimethylsilyl)methyl]-alpha-(methoxycarbonyl)- 4-substituted benzylammonium salts (7) gave two Stevens rearrangement products: methyl 3-(dimethylamino)-2-(4-substituted phenyl)propionates (13) from N-methylides 8, and methyl 3-(dimethylamino)-3-(4-substituted phenyl)propionates (15) from N-benzylides 10. Additional Stevens rearrangement products, methyl 2-(dimethylamino)-3-(4-substituted phenyl)propionates (16), were competitively formed from ylides 12 when the cesium fluoride used was not predried. The mechanism of the isomerization from methylides 8, which was initially generated, to 10 and 12 is discussed.