pent-4-enyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate | 397300-83-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: pent-4-enyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate
• 英文别名: 4-pentenyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate
• CAS: 397300-83-3
• 化学式: C₁₃H₂₃NO₃
• 分子量: 241.331
• InChiKey: FBHCOMNPHBUVMH-UHFFFAOYSA-N

物化性质

• 沸点：
  302.1±42.0 °C(Predicted)
• 密度：
  0.979±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  pent-4-enyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate 在 甲烷磺酸 、 仲丁基锂 、 zinc(II) chloride 、 鹰爪豆碱 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 为溶剂， 反应 29.08h， 生成 (5S)-1-十五碳烯-6-炔-5-醇
  参考文献：
  名称：

  The Preparation of Nonracemic Secondary α-(Carbamoyloxy)alkylzinc and Copper Reagents. A Versatile Approach to Enantioenriched Alcohols

  摘要：

  GRAPHICSChiral alpha-(carbamoyloxy)alkyllithium reagents, prepared using Hoppe's sBuLi/(-)-sparteine methodology, were transmetalated with ZnCl2. Further transmetalation with CuCN with overall retention of configuration gave chiral species that reacted with various electrophiles to give enantiomerically pure alcohols after deprotection. A short, highly efficient synthesis of an industrially relevant pheromone, japonilure, illustrates the value of the methodology.

  DOI：

  10.1021/ol016986e
• 作为产物：
  描述：

  4-戊烯-1-醇 、 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carbonyl chloride 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 120.5h， 以99%的产率得到pent-4-enyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate
  参考文献：
  名称：

  Determination of the Effect of Cation−π Interactions on the Stability of α-Oxy-Organolithium Compounds

  摘要：

  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.

  DOI：

  10.1021/jo801176d

文献信息

• The Preparation of Nonracemic Secondary α-(Carbamoyloxy)alkylzinc and Copper Reagents. A Versatile Approach to Enantioenriched Alcohols
  作者：Julien P. N. Papillon、Richard J. K. Taylor

  DOI：10.1021/ol016986e

  日期：2002.1.1

  GRAPHICSChiral alpha-(carbamoyloxy)alkyllithium reagents, prepared using Hoppe's sBuLi/(-)-sparteine methodology, were transmetalated with ZnCl2. Further transmetalation with CuCN with overall retention of configuration gave chiral species that reacted with various electrophiles to give enantiomerically pure alcohols after deprotection. A short, highly efficient synthesis of an industrially relevant pheromone, japonilure, illustrates the value of the methodology.
• 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.