2-phenylethyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate | 1048703-29-2

• 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: 2-phenylethyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate
• CAS: 1048703-29-2
• 化学式: C₁₆H₂₃NO₃
• 分子量: 277.364
• InChiKey: YHNZSOHIFXDJSI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.21
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  38.77
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-phenylethyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate 、 对溴甲苯 在 四甲基乙二胺 、 仲丁基锂 、 zinc diacetate 、 tris-(dibenzylideneacetone)dipalladium(0) 、 2-二环己基磷-2',6'-二异丙氧基-1,1'-联苯 作用下， 以 乙醚 、 正己烷 、 四氢呋喃 、 甲苯 为溶剂， 反应 23.0h， 以81%的产率得到2-phenyl-1-(p-tolyl)ethyl 2,2,4,4-tetramethyloxazolidine-3-carboxylate
  参考文献：
  名称：

  Enantioselective α-Arylation of O-Carbamates via Sparteine-Mediated Lithiation and Negishi Cross-Coupling

  摘要：

  A general and enantioselective arylation of carbamates derived from primary alcohols was developed by combining Hoppe's sparteine-mediated asymmetric lithiation with Negishi cross-coupling. Coupled with Aggarwal's lithiation-borylation sequence, the current method provides a short and divergent access to a variety of enantioenriched secondary and tertiary benzylic alcohols.

  DOI：

  10.1021/acs.orglett.6b03472
• 作为产物：
  描述：

  2,2,4,4-四甲基-1,3-恶唑烷 在 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 mineral oil 、 苯 为溶剂， 反应 32.5h， 生成 2-phenylethyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate
  参考文献：
  名称：

  Enantioselective α-Arylation of O-Carbamates via Sparteine-Mediated Lithiation and Negishi Cross-Coupling

  摘要：

  A general and enantioselective arylation of carbamates derived from primary alcohols was developed by combining Hoppe's sparteine-mediated asymmetric lithiation with Negishi cross-coupling. Coupled with Aggarwal's lithiation-borylation sequence, the current method provides a short and divergent access to a variety of enantioenriched secondary and tertiary benzylic alcohols.

  DOI：

  10.1021/acs.orglett.6b03472

文献信息

• Determination of the Effect of Cation−π Interactions on the Stability of α-Oxy-Organolithium Compounds
  作者：Pablo Monje、M. Rita Paleo、Luis García-Río、F. Javier Sardina

  DOI：10.1021/jo801176d

  日期：2008.9.19

  Sn-Li exchange equilibria have allowed the quantification of the stabilizing effect of cation-pi interactions in organolithium chemistry. Stabilization energy data on the effect of Li-pi complexation of an aromatic ring or a C=C double bond in organolithium compounds are presented. The amount of stabilization gained by complexation of the Li atom with a pi system in alpha-oxy-organolithium compounds is quite comparable to the one observed in systems containing Li-N or Li-O interactions.