(S)-3-(1'-Oxopropyl-3'-phenyl)-4,5,5-trimethyloxazolidin-2-one | 168297-95-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (S)-3-(1'-Oxopropyl-3'-phenyl)-4,5,5-trimethyloxazolidin-2-one
• 英文别名: (4S)-4,5,5-trimethyl-3-(3-phenylpropanoyl)-1,3-oxazolidin-2-one
• CAS: 168297-95-8
• 化学式: C₁₅H₁₉NO₃
• 分子量: 261.321
• InChiKey: GHBRJZXGGWARQQ-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 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：

  (S)-3-(1'-Oxopropyl-3'-phenyl)-4,5,5-trimethyloxazolidin-2-one 在 lithium hydroxide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 生成 2-methyl-3-phenylpropionic acid
  参考文献：
  名称：

  Identification of a potent and stable antiproliferative agent by the prodrug formation of a thiolate histone deacetylase inhibitor

  摘要：

  To identify prodrugs of a thiolate histone deacetylase inhibitor NCH-31 that show potent antiproliferative activity and are stable in human plasma, we synthesized several candidate prodrugs of NCH-31. Among these compounds, S-2-methyl-3-phenylpropanoyl compound 2 showed more potent antiproliferative activity and higher stability in human plasma than S-isobutyryl compound NCH-51. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.12.117
• 作为产物：
  描述：

  (S)-4-methyl-5,5-dimethyloxazolidin-2-one 、 3-苯丙酰氯 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 以83%的产率得到(S)-3-(1'-Oxopropyl-3'-phenyl)-4,5,5-trimethyloxazolidin-2-one
  参考文献：
  名称：

  Identification of a potent and stable antiproliferative agent by the prodrug formation of a thiolate histone deacetylase inhibitor

  摘要：

  To identify prodrugs of a thiolate histone deacetylase inhibitor NCH-31 that show potent antiproliferative activity and are stable in human plasma, we synthesized several candidate prodrugs of NCH-31. Among these compounds, S-2-methyl-3-phenylpropanoyl compound 2 showed more potent antiproliferative activity and higher stability in human plasma than S-isobutyryl compound NCH-51. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.12.117

文献信息

• 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。
• IMPROVEMENTS IN OR RELATING TO CHIRAL AUXILIARIES
  申请人：OXFORD ASYMMETRY LIMITED

  公开号：EP0736017A1

  公开（公告）日：1996-10-09
• US5801249A
  申请人：——

  公开号：US5801249A

  公开（公告）日：1998-09-01
• [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.