(2R,3S)-3-(p-methoxyphenyl)pyroglutamic acid | 528607-93-4

• 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: (2R,3S)-3-(p-methoxyphenyl)pyroglutamic acid
• 英文别名: (2R,3S)-3-(4-methoxyphenyl)-5-oxopyrrolidine-2-carboxylic acid
• CAS: 528607-93-4
• 化学式: C₁₂H₁₃NO₄
• 分子量: 235.24
• InChiKey: UMYVWXULTPARSE-GXSJLCMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (R,E)-3-[3-(4-methoxyphenyl)acryloyl]-4-phenyloxazolidin-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， 生成 (2R,3S)-3-(p-methoxyphenyl)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

文献信息

• 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
• Application of (S)- and (R)-methyl pyroglutamates as inexpensive, yet highly efficient chiral auxiliaries in the asymmetric Michael addition reactions
  作者：Chaozhong Cai、Takeshi Yamada、Rohit Tiwari、Victor J. Hruby、Vadim A. Soloshonok

  DOI：10.1016/j.tetlet.2004.07.096

  日期：2004.9

  N-(E-enoyl)pyroglutamates, derived from inexpensive and readily available in both enantiomeric forms pyroglutamic acid were found to be an efficient Michael acceptors in the addition reactions with nucleophilic glycine equivalent allowing for an efficient practical asymmetric synthesis of β-substituted pyroglutamic acids and related compounds.

  N-（E-烯丙基）焦谷氨酸甲酯，源自廉价且容易以两种对映体形式焦谷氨酸得到，在亲核甘氨酸当量的加成反应中是有效的迈克尔受体，可有效地实际不对称合成β-取代的焦谷氨酸。酸和相关化合物。
• Asymmetric Michael addition reactions of chiral Ni(II)-complex of glycine with (N-trans-enoyl)oxazolidines: improved reactivity and stereochemical outcome
  作者：Vadim A Soloshonok、Chaozhong Cai、Victor J Hruby

  DOI：10.1016/s0957-4166(99)00483-8

  日期：1999.11

  Application of the (N-trans-enoyl)oxazolidines as Michael acceptors in the kinetically controlled additions with a Ni(II)-complex of the chiral Schiff base of glycine with (S)-o-[N-(N-benzylprolyl)amino]benzophenone 1 was shown to be synthetically advantageous over the alkyl enoylates, allowing for remarkable improvement in reactivity and, in most cases, diastereoselectivity of the reactions. While the stereochemical outcome of the Michael additions of the aliphatic (N-trans-enoyl)oxazolidines with complex 1 depended on the steric bulk of the alkyl group on the starting oxazolidines, the diastereoselectivity of the aromatic (N-trans-enoyl)oxazolidines reactions was found to be controlled by the electronic properties of the aryl ring. In particular, the additions of complex 1 with (N-cinnamoyl)oxazolidines, bearing electron-withdrawing substituents on the phenyl ring, afforded the (2S,3R)configured products with synthetically useful selectivity and in quantitative chemical yield, thus allowing an efficient access to sterically constrained beta-substituted pyroglutamic acids and related compounds. (C) 1999 Elsevier Science Ltd. All rights reserved.
• 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