tert-butyl (2R)-2-[(R)-hydroxy(phenyl)methyl]-4,4-dimethyl-1,3-oxazolidine-3-carboxylate | 216760-01-9

• 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: tert-butyl (2R)-2-[(R)-hydroxy(phenyl)methyl]-4,4-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 216760-01-9
• 化学式: C₁₇H₂₅NO₄
• 分子量: 307.39
• InChiKey: QIWHIYZELUKYPF-ZIAGYGMSSA-N

物化性质

• 沸点：
  415.6±35.0 °C(Predicted)
• 密度：
  1.126±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (2R)-2-[(R)-hydroxy(phenyl)methyl]-4,4-dimethyl-1,3-oxazolidine-3-carboxylate 在 sodium hydride 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (2R)-4,4-dimethyl-2-[(R)-phenyl(phenylmethoxy)methyl]-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
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 alkaline earth salt of/the/ methylsulfuric acid 在 4-二甲氨基吡啶 、 仲丁基锂 、 鹰爪豆碱 作用下， 生成 tert-butyl (2R)-2-[(R)-hydroxy(phenyl)methyl]-4,4-dimethyl-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

文献信息

• 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.