3-(3-anilinobutanoyl)-1,3-oxazolidin-2-one

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-(3-anilinobutanoyl)-1,3-oxazolidin-2-one
• 英文别名: 3-(3-phenylamino-butyroyl)-oxazolidin-2-one；(S)-3-(3-phenylaminobutyryl)-oxazolidin-2-one；3-[(3S)-3-anilinobutanoyl]-1,3-oxazolidin-2-one
• 化学式: C₁₃H₁₆N₂O₃
• 分子量: 248.282
• InChiKey: AMIAZYGZEQQFTI-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(3-anilinobutanoyl)-1,3-oxazolidin-2-one 在 lithium hydroxide 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 18.17h， 生成 S-3-苯氨基丁酸
  参考文献：
  名称：

  Amine-Salt-Controlled, Catalytic Asymmetric Conjugate Addition of Various Amines and Asymmetric Protonation

  摘要：

  The combined use of chiral Pd complex 2 and amine salt enabled completely regulated release of free nucleophilic amine. Under these conditions, an efficient catalytic asymmetric conjugate addition of various amines was achieved to afford beta-amino acid derivatives in high chemical yields with up to 98% ee. Furthermore, a highly enantioselective protonation in 1,4-addition of amine was also developed.

  DOI：

  10.1021/ol0493711
• 作为产物：
  描述：

  3-[(E)-2-丁酰基]-1,3-噁唑烷-2-酮 、 苯胺 在 (BINAP)Pd(II)(Ph₄)⁽²⁺⁾*MeCN*H₂O*[TfO(-)]2 作用下， 以 甲苯 为溶剂， 反应 18.0h， 生成 3-(3-anilinobutanoyl)-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Dicationic [(BINAP)Pd(solvent)2]2+[TfO–]2: enantioselective hydroamination catalyst for alkenoyl-N-oxazolidinones

  摘要：

  在将δ、δ²-不饱和恶唑烷酮与芳香族伯胺（和仲胺）加成时，二价（BINAP）钯（II）络合物具有很高的对映选择性（ee高达 93%）。

  DOI：

  10.1039/b302246c

文献信息

• Facile Synthesis of a New Chiral BINOL–Silica Hybrid Catalyst for Asymmetric Diels–Alder and Aza Michael Reactions
  作者：Hamid Saeidian、Hossein Paghandeh、Zahra Parvin、Zohreh Mirjafary、Mohammad Ghaffarzadeh

  DOI：10.1007/s10562-018-2346-z

  日期：2018.5

  A novel chiral BINOL–silica hybrid has been successfully prepared by the reaction of (S)-BINOL and SiCl4 following by gel polymerization under atmosphere condition. The synthesized catalyst was characterized by elemental analysis, Fourier-transform infrared spectroscopy, X-ray diffraction, scanning electron microscopy and energy-dispersive X-ray spectroscopy. Catalytic activity of the chiral BINOL–silica

  通过 (S)-BINOL 和 SiCl4 在大气条件下进行凝胶聚合反应，成功制备了一种新型手性 BINOL-二氧化硅杂化物。通过元素分析、傅里叶变换红外光谱、X射线衍射、扫描电子显微镜和能量色散X射线光谱对合成的催化剂进行了表征。已经研究了手性 BINOL-二氧化硅杂化物对非对映选择性和对映选择性 Diels-Alder 和 aza Michael 反应的催化活性。温和的反应条件、高产率、出色的非对映体和对映体过量使这种强大而有效的催化剂成为合成手性有机化合物的有吸引力的选择。
• Enantioselective addition of amines to alkenoyl-N-oxazolidinones
  作者：Kelin Li、Pim Huat Phua、King Kuok (Mimi) Hii

  DOI：10.1016/j.tet.2005.03.125

  日期：2005.6

  Investigations of cationic Pd(II) complex 1 as hydroamination catalysts led to the development of highly enantioselective addition of aromatic amines to alkenoyl-N-oxazolidinones, with ee values up to 93%. Factors affecting the yield and selectivity of the reaction were described. Addition of substituted benzylamines to these Michael acceptors was also attempted, and was found to be reversible under

  阳离子Pd（II）配合物1作为加氢胺化催化剂的研究导致开发了高度对映体的芳香胺向烯酰基-N-恶唑烷酮的对映体选择性加成，ee值高达93％。描述了影响反应的产率和选择性的因素。还试图将取代的苄胺加到这些迈克尔受体上，发现在催化条件下是可逆的。
• [EN] PROCESS FOR PRODUCING OPTICALLY ACTIIVE BETA-AMINO ACID DERIVATIVES<br/>[FR] PROCEDE POUR PRODUIRE DES DERIVES D'ACIDES AMINES BETA A ACTIVITE OPTIQUE
  申请人：TAKASAGO PERFUMERY CO LTD

  公开号：WO2005016866A3

  公开（公告）日：2005-04-21
• Amine-Salt-Controlled, Catalytic Asymmetric Conjugate Addition of Various Amines and Asymmetric Protonation
  作者：Yoshitaka Hamashima、Hidenori Somei、Yuta Shimura、Toshihiro Tamura、Mikiko Sodeoka

  DOI：10.1021/ol0493711

  日期：2004.5.1

  The combined use of chiral Pd complex 2 and amine salt enabled completely regulated release of free nucleophilic amine. Under these conditions, an efficient catalytic asymmetric conjugate addition of various amines was achieved to afford beta-amino acid derivatives in high chemical yields with up to 98% ee. Furthermore, a highly enantioselective protonation in 1,4-addition of amine was also developed.
• Dicationic [(BINAP)Pd(solvent)2]2+[TfO–]2: enantioselective hydroamination catalyst for alkenoyl-N-oxazolidinones
  作者：Kelin Li、King Kuok (Mimi) Hii

  DOI：10.1039/b302246c

  日期：2003.4.30

  Dicationic (BINAP)palladium(II) complex induced high enantioselectiviies in the addition of primary (and secondary) aromatic amines to α, β-unsaturated oxazolidinones (up to 93% ee).

  在将δ、δ²-不饱和恶唑烷酮与芳香族伯胺（和仲胺）加成时，二价（BINAP）钯（II）络合物具有很高的对映选择性（ee高达 93%）。