Diphenylketene N-<1,1-bis(trimethylsilyl)ethyl>imine

• 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: Diphenylketene N-<1,1-bis(trimethylsilyl)ethyl>imine
• 化学式: C₂₂H₃₁NSi₂
• 分子量: 365.666
• InChiKey: SQDOOKJZDIQCTN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  二苯乙烯酮 在 甲基锂 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 3.0h， 生成 Diphenylketene N-<1,1-bis(trimethylsilyl)ethyl>imine
  参考文献：
  名称：

  Synthesis and Reactivity of N-[Bis(trimethylsilyl)methyl]heterocumulenes

  摘要：

  A number of N-heterocumulenes bearing the (Me(3)Si)(2)CH (BSM) substituent adjacent to the terminal nitrogen atom of the heterocumulene function, namely BSM-N=C=O (2), BSM-N=C=S (3), BSM-N=C=NR(4: R = BSM; 5: R = C6H5), BSM-N=C=CR(1)R(2) (9a: R(1) = R(2) = C6H5; 9b: R(1) = H, R(2) = SiMe(3); 10: R(1) = R(2) = CH3; 12: R(1) = H; R(2) = CH3), and BSM-N=S=O (14), have been synthesized. The synthetic utility of the BSM-N-substituted heterocumulenes has been explored through the creation of a carbanion center at the a position relative to nitrogen. In particular, the following reactions have been studied: (i) the nucleophilic addition of MeLi to compounds 2 and 5, (ii) the MeLi-induced deprotonation of ketene imines 9a,b (this investigation includes the study of the regiochemical output of the addition of electrophiles (H2O, Mel, Me(2)CHI) to the resulting 1,3-dipoles; and (iii) the TBAF-induced desilylation of compounds 2 and 9a followed by reaction with benzaldehyde.

  DOI：

  10.1021/jo00124a011

文献信息

• Synthesis and Reactivity of N-[Bis(trimethylsilyl)methyl]heterocumulenes
  作者：Gaetano Barbaro、Arturo Battaglia、Patrizia Giorgianni、Andrea Guerrini、Giancarlo Seconi

  DOI：10.1021/jo00124a011

  日期：1995.9

  A number of N-heterocumulenes bearing the (Me(3)Si)(2)CH (BSM) substituent adjacent to the terminal nitrogen atom of the heterocumulene function, namely BSM-N=C=O (2), BSM-N=C=S (3), BSM-N=C=NR(4: R = BSM; 5: R = C6H5), BSM-N=C=CR(1)R(2) (9a: R(1) = R(2) = C6H5; 9b: R(1) = H, R(2) = SiMe(3); 10: R(1) = R(2) = CH3; 12: R(1) = H; R(2) = CH3), and BSM-N=S=O (14), have been synthesized. The synthetic utility of the BSM-N-substituted heterocumulenes has been explored through the creation of a carbanion center at the a position relative to nitrogen. In particular, the following reactions have been studied: (i) the nucleophilic addition of MeLi to compounds 2 and 5, (ii) the MeLi-induced deprotonation of ketene imines 9a,b (this investigation includes the study of the regiochemical output of the addition of electrophiles (H2O, Mel, Me(2)CHI) to the resulting 1,3-dipoles; and (iii) the TBAF-induced desilylation of compounds 2 and 9a followed by reaction with benzaldehyde.