(2R,4R)-N-(2,4,6-trimethoxybenzyl)-2,4-diphenyl-1,3-oxazolidine | 205526-45-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2R,4R)-N-(2,4,6-trimethoxybenzyl)-2,4-diphenyl-1,3-oxazolidine
• 英文别名: (2R,4R)-2,4-diphenyl-3-[(2,4,6-trimethoxyphenyl)methyl]-1,3-oxazolidine
• CAS: 205526-45-0
• 化学式: C₂₅H₂₇NO₄
• 分子量: 405.494
• InChiKey: BPCXVPQTOGIBLX-WIOPSUGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  40.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,4R)-N-(2,4,6-trimethoxybenzyl)-2,4-diphenyl-1,3-oxazolidine 在 lead(IV) acetate 、 magnesium 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 230.0h， 生成 (2R,6S)-2,6-diphenylpiperidine
  参考文献：
  名称：

  Facile Diastereoselective Reactions of Chiral 1,3-Oxazolidines with Grignard Reagents; Asymmetric Syntheses of 2-Substituted and 2,6-Disubstituted Piperidines

  摘要：

  DOI：

  10.3987/com-97-s32
• 作为产物：
  描述：

  2,4,6-三甲氧基苯甲醛 在 3 A molecular sieve 作用下， 以 苯 为溶剂， 反应 1.0h， 生成 (2R,4R)-N-(2,4,6-trimethoxybenzyl)-2,4-diphenyl-1,3-oxazolidine
  参考文献：
  名称：

  Stereocontrolled Addition of Grignard Reagents to Chiral 1,3-Oxazolidines Having N-Methoxybenzyl Groups: Effect of N-Substituent in Diastereoselectivity

  摘要：

  Chiral 1,3-oxazolidines having various N-methoxybenzyl groups were synthesized from (R)-phenylglycinol in three steps. The reactions of chiral 1,3-oxazolidines with Grignard reagents proceeded gently to give the corresponding chiral amines in quantitative yield and high diastereoselectivity. The best results regarding diastereoselectivity were achieved using a chiral 1,3-oxazolidine having N-2,4,6-trimethoxybenzyl moiety. These nitrogen functional groups could be easily removed from the chiral amines using TFA.

  DOI：

  10.3987/com-98-8211

文献信息

• Facile Diastereoselective Reactions of Chiral 1,3-Oxazolidines with Grignard Reagents; Asymmetric Syntheses of 2-Substituted and 2,6-Disubstituted Piperidines
  作者：Kimio Higashiyama、Hadi Poerwono、Takayasu Yamauchi、Hiroshi Takahashi

  DOI：10.3987/com-97-s32

  日期：——
• Stereocontrolled Addition of Grignard Reagents to Chiral 1,3-Oxazolidines Having N-Methoxybenzyl Groups: Effect of N-Substituent in Diastereoselectivity
  作者：Takayasu Yamauchi、Hiroshi Takahashi、Kimio Higashiyama

  DOI：10.3987/com-98-8211

  日期：——

  Chiral 1,3-oxazolidines having various N-methoxybenzyl groups were synthesized from (R)-phenylglycinol in three steps. The reactions of chiral 1,3-oxazolidines with Grignard reagents proceeded gently to give the corresponding chiral amines in quantitative yield and high diastereoselectivity. The best results regarding diastereoselectivity were achieved using a chiral 1,3-oxazolidine having N-2,4,6-trimethoxybenzyl moiety. These nitrogen functional groups could be easily removed from the chiral amines using TFA.