(4R)-3-<3'-phenyl-2'(E)-propenoyl>-4-phenyl-5,5-dimethyloxazolidin-2-one | 168298-08-6

• 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: (4R)-3-<3'-phenyl-2'(E)-propenoyl>-4-phenyl-5,5-dimethyloxazolidin-2-one
• 英文别名: (R)-4-phenyl-5,5-dimethyl-3-[(E)-(3-phenylacryloyl)]oxazolidin-2-one；(R)-5,5-dimethyl-4-phenyl-3-[(E)-3-phenylacryloyl]oxazolidin-2-one；(4R)-3-[3-Phenyl-2(E)-propenoyl]-4-phenyl-5,5-dimethyloxazolidin-2-one；(r)-5,5-Dimethyl-4-phenyl-3-[(e)-3-phenylacryloyl] oxazolidin-2-one；(4R)-5,5-dimethyl-4-phenyl-3-[(E)-3-phenylprop-2-enoyl]-1,3-oxazolidin-2-one
• CAS: 168298-08-6
• 化学式: C₂₀H₁₉NO₃
• 分子量: 321.376
• InChiKey: MXSFCYIFPDPOSF-KAUXGEHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4R)-3-<3'-phenyl-2'(E)-propenoyl>-4-phenyl-5,5-dimethyloxazolidin-2-one 在 三溴化硼 、 magnesium 作用下， 以 氘代四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 (4R)-6-甲基-4-苯基色满-2-酮
  参考文献：
  名称：

  Conjugate addition of aryl nucleophiles to α,β-unsaturated cinnamic acid derivatives containing Evans type chiral auxiliaries

  摘要：

  Cinnamides containing oxazolidin-2-one type auxiliaries have been prepared. A novel pathway to chiral 4-aryl-6-methyl-3,4-dihydrocoumrines via the asymmetric conjugate addition of arylmagnesium bromides to these cinnamides is described. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.07.003
• 作为产物：
  描述：

  (R)-5,5-二甲基-4-苯基-2-恶唑烷酮 在 正丁基锂 、 sodium hydride 、 potassium iodide 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.25h， 生成 (4R)-3-<3'-phenyl-2'(E)-propenoyl>-4-phenyl-5,5-dimethyloxazolidin-2-one
  参考文献：
  名称：

  SYNTHESIS OF THE CHIRAL α,β-UNSATURATED N-ACYL-OXAZOLIDIN-2-ONES BY WITTIG REACTION

  摘要：

  A new, universal, and versatile method has been developed for the synthesis of the chiral alpha,beta-unsaturated N-acyl-oxazolidin-2-ones 4 based on the Wittig reaction of the triphenylphosphonium salt 7 derived from, the (R)-3-(2-Chloro-acetyl)-5,5-dimethyl-4-pheny-oxazolidin-2-one 6.

  DOI：

  10.1080/10426500490468155

文献信息

• The ?SuperQuat? (R)-4-phenyl-5,5-dimethyl oxazolidin-2-one as an effective chiral auxiliary for conjugate additions: Asymmetric synthesis of (?)-Aplysillamide B
  作者：Stephen G. Davies、Hitesh J. Sanganee、Peter Szolcsanyi

  DOI：10.1016/s0040-4020(98)01145-4

  日期：1999.3

  (R)-4-Phenyl-5,5-dimethyl-oxazolidin-2-one, readily available from d-phenylglycine, is shown to be an effective chiral auxiliary for stereoselective conjugate additions to attached α,β-unsaturated N-acyl moieties. Its utility is demonstrated by the asymmetric synthesis of the antifungal, antibacterial (−)-Aplysillamide B.

  可以容易地从d-苯基甘氨酸获得的（R）-4-苯基-5,5-二甲基-恶唑烷-2--2-酮是对立体选择性共轭加成到连接的α，β-不饱和N-酰基部分的有效手性助剂。抗真菌，抗菌（-）-Aplysillamide B的不对称合成证明了其实用性。
• 4-Substituted-5,5-dimethyl oxazolidin-2-ones as effective chiral auxiliaries for enolate alkylations and Michael additions
  作者：Stephen G. Davies、Hitesh J. Sanganee

  DOI：10.1016/0957-4166(95)00057-v

  日期：1995.3

  4-(Methyl, phenyl, benzyl, and i-propyl)-5,5-dimethyl-oxazolidin-2-ones, readily available from α-amino acids, are shown to be effective chiral auxiliaries for stereoselective enolate alkylations and conjugate additions of attached N-acyl moieties.

  4-（甲基，苯基，苄基，和我-丙基）-5,5-二甲基-恶唑烷-2-酮，可容易地从α氨基酸，被证明是有效的立体选择性为烯醇化物烷基化和的共轭加成的手性助剂连接的N-酰基部分。
• Chiral auxiliaries
  申请人：Oxford Asymmetry International plc

  公开号：US05801249A1

  公开（公告）日：1998-09-01

  This invention relates to novel compounds of general formula (I): ##STR1## wherein the two R.sup.1 groups are identical lower alkyl groups or together form a lower alkylene group; R.sup.2 and R.sup.3 are both different and are selected from hydrogen atoms or organic groups; X and X', which may be the same or different, are selected from O, S and NR, where R represents an organic group; and the asterisk denotes that the configurations of R.sup.2 and R.sup.3 are such that the compound (I) is in substantially enantiomerically pure 4R- or 4S-form. The compounds are useful chiral auxiliaries to which a wide range of, for example, acyl groups containing prochiral centers may be readily and reversibly coupled to the 3-position amino group.

  本发明涉及一种新型化合物，其一般式为(I)：##STR1## 其中两个R1基团是相同的低碳基基团或共同形成一个低碳基烷基基团；R2和R3都不同，可选择氢原子或有机基团；X和X'可以相同也可以不同，可选择O、S和NR，其中R代表有机基团；星号表示R2和R3的构型使得化合物(I)基本上是对映异构体纯度为4R或4S形式。这些化合物是有用的手性辅助剂，可以将广泛的含有原子中心的丙酰基基团轻松可逆地耦合到3位氨基基团上。
• Studies on the Synthesis and Dynamic NMR Properties of 2-(Benzylidene amino)-N-[(R)-2-hydroxy-2-methyl-1-phenylpropyl]acetamide
  作者：H.A. Samimi、M. Mamaghani、K. Tabatabeian、H.R. Bijanzadeh

  DOI：10.1007/bf03245877

  日期：2010.3

  An efficient method was employed for the preparation of 2-(benzylideneamino)-N-[(R)-2-hydroxy-2-methyl-1-phenylpropyl] acetamide utilizing optically pure (R)-5,5-dimethyl-4-phenyloxazolidin-2-one. This product showed interesting dynamic NMR properties for the methylene protons adjacent to the azomethine group (Delta G double dagger = 15.1 +/- 0.1 kcal mol(-1)).
• [EN] IMPROVEMENTS IN OR RELATING TO CHIRAL AUXILIARIES<br/>[FR] AMELIORATIONS APPORTEES A DES AUXILIAIRES CHIRAUX
  申请人：OXFORD ASYMMETRY LIMITED

  公开号：WO1995018112A1

  公开（公告）日：1995-07-06

  (EN) Novel compounds of general formula (I) (where the two R1 groups are identical lower alkyl groups or together form a lower alkylene group; R2 and R3 are both different and are selected from hydrogen atoms and organic groups; X and X', which may be the same or different, are selected from O, S and NR, where R represents an organic group; and the asterisk denotes that the configurations of R2 and R3 are such that the compound (I) is in substantially enantiomerically pure 4R- or 4S-form). The compounds are useful chiral auxiliaries to which a wide range of e.g. acyl groups containing prochiral centres may be readily and reversibly coupled to the 3-position amino group.(FR) L'invention se rapporte à de nouveaux composés de la formule générale (I) (dans laquelle les deux groupes R1 sont des groupes d'alkyle inférieur identiques ou forment ensemble un groupe alkylène inférieur; R2 et R3 sont tous les deux différents et sont sélectionnés parmi des atomes d'hydrogène et des groupes organiques; X et X', qui peuvent être identiques ou différents, sont sélectionnés parmi, O, S et NR, où R représente un groupe organique; et l'astérisque indique que les configurations de R2 et R3 sont telles que le composé (I) se présente sous une forme 4R- ou 4S- pratiquement énantiomériquement pure). Les composés selon l'invention sont des auxiliaires chiraux utiles auquels un large éventail de groupes acyle, par exemple, contenant des centres prochiraux, peuvent être couplés facilement et de manière réversible au groupe amino en position 3.