(R)-3-(1-naphthoyl)-4-((R)-(2-bromophenyl)(hydroxy)methyl)-2,2,4-trimethyloxazolidin-5-one | 1539291-93-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-3-(1-naphthoyl)-4-((R)-(2-bromophenyl)(hydroxy)methyl)-2,2,4-trimethyloxazolidin-5-one
• 英文别名: (4R)-4-[(R)-(2-bromophenyl)-hydroxymethyl]-2,2,4-trimethyl-3-(naphthalene-1-carbonyl)-1,3-oxazolidin-5-one
• CAS: 1539291-93-4
• 化学式: C₂₄H₂₂BrNO₄
• 分子量: 468.347
• InChiKey: OALZPOWRRAMQAI-HYBUGGRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-3-(1-naphthoyl)-4-((R)-(2-bromophenyl)(hydroxy)methyl)-2,2,4-trimethyloxazolidin-5-one 在 盐酸 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 24.0h， 以100%的产率得到(2R,3R)-2-amino-3-(2-bromophenyl)-3-hydroxy-2-methylpropanoic acid hydrochloride
  参考文献：
  名称：

  Substrate Control in Enantioselective and Diastereoselective Aldol Reaction by Memory of Chirality: A Rapid Access to Enantiopure β-Hydroxy Quaternary α-Amino Acids

  摘要：

  An asymmetric aldol reaction by memory of chirality is reported with a substrate control of stereoselectivity by aldehyde and rationalized. Starting from L-alanine, several diastereopure and enantioenriched beta-hydroxy quaternary alpha-amino acids have been obtained in three steps. The initial chirality of L-alanine is memorized through the dynamic axial chirality of tertiary aromatic amide.

  DOI：

  10.1021/ol403523e
• 作为产物：
  描述：

  (4S)-2,2,4-trimethyl-1,3-oxazolidin-5-one 在 三甲基铝 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 丙酮 、 甲苯 为溶剂， 反应 2.21h， 生成 (R)-3-(1-naphthoyl)-4-((R)-(2-bromophenyl)(hydroxy)methyl)-2,2,4-trimethyloxazolidin-5-one 、 (S)-3-(1-naphthoyl)-4-((S)-(2-bromophenyl)(hydroxy)methyl)-2,2,4-trimethyloxazolidin-5-one 、 (R)-3-(1-naphthoyl)-4-((S)-(2-bromophenyl)(hydroxy)methyl)-2,2,4-trimethyloxazolidin-5-one
  参考文献：
  名称：

  Substrate Control in Enantioselective and Diastereoselective Aldol Reaction by Memory of Chirality: A Rapid Access to Enantiopure β-Hydroxy Quaternary α-Amino Acids

  摘要：

  An asymmetric aldol reaction by memory of chirality is reported with a substrate control of stereoselectivity by aldehyde and rationalized. Starting from L-alanine, several diastereopure and enantioenriched beta-hydroxy quaternary alpha-amino acids have been obtained in three steps. The initial chirality of L-alanine is memorized through the dynamic axial chirality of tertiary aromatic amide.

  DOI：

  10.1021/ol403523e

文献信息

• Substrate Control in Enantioselective and Diastereoselective Aldol Reaction by Memory of Chirality: A Rapid Access to Enantiopure β-Hydroxy Quaternary α-Amino Acids
  作者：Baby Viswambharan、Didier Gori、Régis Guillot、Cyrille Kouklovsky、Valérie Alezra

  DOI：10.1021/ol403523e

  日期：2014.2.7

  An asymmetric aldol reaction by memory of chirality is reported with a substrate control of stereoselectivity by aldehyde and rationalized. Starting from L-alanine, several diastereopure and enantioenriched beta-hydroxy quaternary alpha-amino acids have been obtained in three steps. The initial chirality of L-alanine is memorized through the dynamic axial chirality of tertiary aromatic amide.