(S)-4-phenyl-3-{(E)-3-[4-(trifluoromethyl)phenyl]prop-2-enoyl}-1,3-oxazolidin-2-one | 264626-04-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (S)-4-phenyl-3-{(E)-3-[4-(trifluoromethyl)phenyl]prop-2-enoyl}-1,3-oxazolidin-2-one
• 英文别名: (S)-N-[(E)-4-CF3C6H4CHCHC(O)]-4-phenyl-1,3-oxazolidin-2-one；(4S)-4-phenyl-3-[(E)-3-[4-(trifluoromethyl)phenyl]prop-2-enoyl]-1,3-oxazolidin-2-one
• CAS: 264626-04-2
• 化学式: C₁₉H₁₄F₃NO₃
• 分子量: 361.32
• InChiKey: BPIITRPDBHXIGT-YCABEKBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-4-phenyl-3-{(E)-3-[4-(trifluoromethyl)phenyl]prop-2-enoyl}-1,3-oxazolidin-2-one 在 氨 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 (2S,3R)-3-(p-trifluoromethylphenyl)pyroglutamic acid
  参考文献：
  名称：

  对映体纯 3-取代焦谷氨酸和相关化合物的实用不对称合成

  摘要：

  DOI：

  10.1002/1521-3773(20000616)39:12<2172::aid-anie2172>3.0.co;2-0
• 作为产物：
  描述：

  4-三氟甲基肉桂酸 在 氯化亚砜 、 三乙胺 、 lithium chloride 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 (S)-4-phenyl-3-{(E)-3-[4-(trifluoromethyl)phenyl]prop-2-enoyl}-1,3-oxazolidin-2-one
  参考文献：
  名称：

  A Convenient, Room-Temperature–Organic Base Protocol for Preparing Chiral 3-(Enoyl)-1,3-oxazolidin-2-ones

  摘要：

  In this study, we developed a new protocol for the preparation of the chiral 3-[(E)-enoyl]-1,3-oxazolidin-2-ones under the ultimately simple reaction conditions starting with the corresponding enoyl chlorides and 1,3-oxazolidin-2-ones with Et3N/LiCl at room temperature. The method generally allows efficient preparation of various derivatives regardless of the steric and electronic nature of the substituents on both the enoyl or the oxazolidinone sites. Excellent yields, combined with the simplicity of the experimental procedures, render the present method immediately useful for preparing the target compounds.

  DOI：

  10.1002/1522-2675(200211)85:11<3616::aid-hlca3616>3.0.co;2-o

文献信息

• NH-type of chiral Ni(ii) complexes of glycine Schiff base: design, structural evaluation, reactivity and synthetic applications
  作者：Mackenzie Bergagnini、Kazunobu Fukushi、Jianlin Han、Norio Shibata、Christian Roussel、Trevor K. Ellis、José Luis Aceña、Vadim A. Soloshonok

  DOI：10.1039/c3ob41959b

  日期：——

  of “N–H” Ni(II) complexes of glycine Schiff bases and study general aspects of their reactivity. It was confirmed that the presence of NH function in these Ni(II) complexes does not interfere with the homologation of the glycine residue, rendering these derivatives of high synthetic value for the general synthesis of α-amino acids. In particular, the practical application of these NH-type complexes was

  此处报道的工作涉及甘氨酸席夫碱的新型“ NH” Ni（II）配合物的设计，并研究其反应性的一般方面。已证实在这些Ni（II）络合物中NH功能的存在不会干扰甘氨酸残基的同源性，从而使这些衍生物对于α-氨基酸的一般合成具有很高的合成价值。特别是，通过与手性迈克尔受体的迈克尔加成反应，通过不对称合成各种β-取代的焦谷氨酸，证明了这些NH型配合物的实际应用。
• Michael Addition Reactions between Chiral Equivalents of a Nucleophilic Glycine and (<i>S</i>)- or (<i>R</i>)-3-[(<i>E</i>)-Enoyl]-4-phenyl-1,3-oxazolidin-2-ones as a General Method for Efficient Preparation of β-Substituted Pyroglutamic Acids. Case of Topographically Controlled Stereoselectivity
  作者：Vadim A. Soloshonok、Chaozhong Cai、Takeshi Yamada、Hisanori Ueki、Yasufumi Ohfune、Victor J. Hruby

  DOI：10.1021/ja0535561

  日期：2005.11.1

  This paper describes a systematic study of addition reactions between the chiral Ni(II) complex of the Schiff base of glycine with (S)-o-[N-(N-benzylprolyl)amino]benzophenone and (S)- or (R)-3-[(E)-enoyl]-4-phenyl-1,3-oxazolidin-2-ones as a general and synthetically efficient approach to beta-substituted pyroglutamic acids and relevant compounds. These reactions were shown to occur at room temperature

  本文描述了甘氨酸席夫碱的手性 Ni(II) 配合物与 (S)-o-[N-(N-benzylprolyl)amino] 二苯甲酮和 (S)- 或 (R) 之间的加成反应的系统研究-3-[(E)-enoyl]-4-phenyl-1,3-oxazolidin-2-ones 作为 β 取代焦谷氨酸和相关化合物的通用且合成有效的方法。这些反应在室温下在非螯合有机碱的存在下发生，最值得注意的是，在两个新形成的立体中心都具有非常高的立体选择性（> 98% 非对映体过量 (de)）。发现反应的立体化学结果主要受迈克尔受体的立体化学偏好控制，甘氨酸配合物的手性仅影响反应速率。因此，在 (S) 构型的 Ni(II) 配合物和迈克尔受体的反应中，反应速率都非常高，可以制备具有几乎定量 (>98%) 化学和立体化学产率的相应产物。相比之下，(S)-配置的 Ni(II) 配合物和 (R)-配置的迈克尔受体的反应以明
• Ionic Liquid Media Resulted in the First Asymmetric Aminohalogenation Reaction of Alkenes
  作者：Xin Xu、S. R. S. Saibabu Kotti、Junying Liu、John F. Cannon、Allan D. Headley、Guigen Li

  DOI：10.1021/ol048045i

  日期：2004.12.1

  [Graphics]The first asymmetric aminohalogenation of functionalized alkenes has been established. The ionic liquid [bmim][BF4] was found to be the only effective media for success as normal organic solvents failed to give any product for this reaction. The reaction is also very convenient to perform by simply mixing the three reactants, cinnamates, N,N-dichloro-p-toluenesulfonamide, and catalyst, together with 4 A molecular sieves at room temperature in [bmim][BF4] in any convenient vial of appropriate size without special protection from inert gases. Good chemical yields (60-72%) and diastereoselectivities (up to 75% de) have been obtained with a good scope of substrates. The resulting individual diastereomers have been cleanly separated via column chromatography. The absolute stereochemistry of the reaction was unambiguously determined by X-ray structural analysis.
• A Convenient, Room-Temperature–Organic Base Protocol for Preparing Chiral 3-(Enoyl)-1,3-oxazolidin-2-ones
  作者：Vadim A. Soloshonok、Hisanori Ueki、Changchun Jiang、Chaozhong Cai、Victor J. Hruby

  DOI：10.1002/1522-2675(200211)85:11<3616::aid-hlca3616>3.0.co;2-o

  日期：2002.11

  In this study, we developed a new protocol for the preparation of the chiral 3-[(E)-enoyl]-1,3-oxazolidin-2-ones under the ultimately simple reaction conditions starting with the corresponding enoyl chlorides and 1,3-oxazolidin-2-ones with Et3N/LiCl at room temperature. The method generally allows efficient preparation of various derivatives regardless of the steric and electronic nature of the substituents on both the enoyl or the oxazolidinone sites. Excellent yields, combined with the simplicity of the experimental procedures, render the present method immediately useful for preparing the target compounds.
• A Practical Asymmetric Synthesis of Enantiomerically Pure 3-Substituted Pyroglutamic Acids and Related Compounds
  作者：Vadim A. Soloshonok、Chaozhong Cai、Victor J. Hruby

  DOI：10.1002/1521-3773(20000616)39:12<2172::aid-anie2172>3.0.co;2-0

  日期：2000.6.16