N-Boc-4,4-dimethyl-1,3-oxazolidine | 216759-96-5

• 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: N-Boc-4,4-dimethyl-1,3-oxazolidine
• 英文别名: 3-Oxazolidinecarboxylic acid, 4,4-dimethyl-, 1,1-dimethylethyl ester；tert-butyl 4,4-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 216759-96-5
• 化学式: C₁₀H₁₉NO₃
• 分子量: 201.266
• InChiKey: UVMGIUAAUJOLKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 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：

  N-Boc-4,4-dimethyl-1,3-oxazolidine 在 仲丁基锂 、 sodium hydride 、 鹰爪豆碱 作用下， 以 四氢呋喃 为溶剂， 生成 tert-butyl (2R)-4,4-dimethyl-2-[(S)-phenyl(phenylmethoxy)methyl]-1,3-oxazolidine-3-carboxylate
  参考文献：
  名称：

  Formation and reaction of 2-metalated N-Boc-4,4-dimethyl-1,3-oxazolidines in the presence of (−)-sparteine: new chiral formyl anion equivalents

  摘要：

  Lithiation of N-Boc-4,4-dimethyl-1,3-oxazolidine with s-BuLi and the following reaction with benzaldehyde was carried out in the presence of (-)-sparteine. The reaction was not diastereoselective (syn:anti=46:54), but each isomer of the adducts was obtained enantioselectively (syn: 90% ee, anti: 88% eel. Addition of MgBr2 to the reaction mixture increased the diastereoselectivity to syn:anti=90:10. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00319-x
• 作为产物：
  描述：

  聚合甲醛 、 二碳酸二叔丁酯 、 2-氨基-2-甲基-1-丙醇 在 4-二甲氨基吡啶 作用下， 生成 N-Boc-4,4-dimethyl-1,3-oxazolidine
  参考文献：
  名称：

  Formation and reaction of 2-metalated N-Boc-4,4-dimethyl-1,3-oxazolidines in the presence of (−)-sparteine: new chiral formyl anion equivalents

  摘要：

  Lithiation of N-Boc-4,4-dimethyl-1,3-oxazolidine with s-BuLi and the following reaction with benzaldehyde was carried out in the presence of (-)-sparteine. The reaction was not diastereoselective (syn:anti=46:54), but each isomer of the adducts was obtained enantioselectively (syn: 90% ee, anti: 88% eel. Addition of MgBr2 to the reaction mixture increased the diastereoselectivity to syn:anti=90:10. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00319-x

文献信息

• Acylation of α-(N-carbamoyl)alkylcuprates and alkyl- or aryl(halo)cuprates
  作者：R.Karl Dieter、Ram R. Sharma、Huayun Yu、Vinayak K. Gore

  DOI：10.1016/s0040-4020(02)01526-0

  日期：2003.2

  α-(N-Carbamoyl)alkylcuprates [R2CuLi·LiX or RCuXLi (X=CN, Cl)] when prepared from THF soluble CuX·2LiCl (X=Cl, CN) undergo a reliable and generally high yield reaction with aroyl, alkanoyl, and alkenoyl chlorides to provide a rapid and efficient synthesis of α-carbamoyl ketones. Cuprates prepared from acyclic, cyclic, and a functionalized carbamate can be utilized. Although yields are a function of

  由THF可溶性CuX·2LiCl（X = Cl，CN）制备的α-（N-氨基甲酰基）烷基铜酸酯[R 2 CuLi·LiX或RCuXLi（X = CN，Cl）]与芳酰基进行可靠且通常高收率的反应，链烷酰和链烯酰氯，可快速有效地合成α-氨基甲酰基酮。可以利用由无环，环状和官能化的氨基甲酸酯制得的铜酸盐。尽管产率是铜酸盐试剂和底物结构的函数，但是使用由2RLi + CuCN·2LiCl生成的试剂可以获得接近定量的产率。在α-（N-氨基甲酰基）烷基配体，尽管产率略低。由一当量的CuCl·2LiCl和有机锂或格利雅试剂生成的烷基（氯）铜酸盐的酰化为酮合成提供了一种高效且高收率的方法。
• Formation and reaction of 2-metalated N-Boc-4,4-dimethyl-1,3-oxazolidines in the presence of (−)-sparteine: new chiral formyl anion equivalents
  作者：Naoki Kise、Tadashi Urai、Jun-ichi Yoshida

  DOI：10.1016/s0957-4166(98)00319-x

  日期：1998.9

  Lithiation of N-Boc-4,4-dimethyl-1,3-oxazolidine with s-BuLi and the following reaction with benzaldehyde was carried out in the presence of (-)-sparteine. The reaction was not diastereoselective (syn:anti=46:54), but each isomer of the adducts was obtained enantioselectively (syn: 90% ee, anti: 88% eel. Addition of MgBr2 to the reaction mixture increased the diastereoselectivity to syn:anti=90:10. (C) 1998 Elsevier Science Ltd. All rights reserved.