(R)-3-(1-naphthoyl)-4-((R)-hydroxy(phenyl)methyl)-2,2,4-trimethyloxazolidin-5-one | 1539291-86-5

• 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)-hydroxy(phenyl)methyl)-2,2,4-trimethyloxazolidin-5-one
• 英文别名: (4R)-4-[(R)-hydroxy(phenyl)methyl]-2,2,4-trimethyl-3-(naphthalene-1-carbonyl)-1,3-oxazolidin-5-one
• CAS: 1539291-86-5
• 化学式: C₂₄H₂₃NO₄
• 分子量: 389.451
• InChiKey: WEODFFUGQJIAAJ-HYBUGGRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  29
• 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)-hydroxy(phenyl)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98%的产率得到(2R,3R)-2-amino-3-hydroxy-2-methyl-3-phenylpropanoic 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：

  3-(1-naphthoyl)-4-(hydroxy(phenyl)methyl)-2,2,4-trimethyloxazolidin-5-one 以 乙酸乙酯 、 甲苯 、 正戊烷 为溶剂， 以90%的产率得到(R)-3-(1-naphthoyl)-4-((R)-hydroxy(phenyl)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

• Memory of Chirality in a Flow-Based System: Enantioselective Synthesis of Quaternary α-Amino Acids Using Flow Microreactors
  作者：Antonin Mambrini、Didier Gori、Cyrille Kouklovsky、Heejin Kim、Jun-ichi Yoshida、Valérie Alezra

  DOI：10.1002/ejoc.201801305

  日期：2018.12.19

  The first memory‐of‐chirality reaction in flash chemistry is reported: it allows the enantioselective synthesis of quaternary α‐amino acid derivatives with reaction residence times of less than three minutes. This proof of concept shows that larger product quantities can be synthesized in short reaction times.

  据报道，在闪蒸化学中有第一个手性记忆反应：它允许对映体选择性合成季质α-氨基酸衍生物，反应停留时间少于3分钟。这一概念证明表明，可以在较短的反应时间内合成更多的产物。
• 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.