(2R,4S)-3-苯甲酰基-4-甲基-2-苯基-1,3-恶唑烷-5-酮 | 113806-28-3

• 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
• 中文名称: (2R,4S)-3-苯甲酰基-4-甲基-2-苯基-1,3-恶唑烷-5-酮
• 英文名称: (+)-(2R,4S)-3-benzoyl-4-methyl-2-phenyl-1,3-oxazolidin-5-one
• 英文别名: (2R,4S)-3-Benzoyl-4-methyl-2-phenyl-5-oxazolidinone；(2R,4S)-3-benzoyl-4-methyl-2-phenyl-1,3-oxazolidin-5-one
• CAS: 113806-28-3
• 化学式: C₁₇H₁₅NO₃
• 分子量: 281.311
• InChiKey: XWBOGYZALFWLOF-BLLLJJGKSA-N

物化性质

• 溶解度：
  可溶于二氯甲烷、乙酸乙酯、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  (2R,4S)-3-苯甲酰基-4-甲基-2-苯基-1,3-恶唑烷-5-酮 在 palladium diacetate 、 sodium hydroxide 、 lithium hexamethyldisilazane 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 2.17h， 生成 (1R,2R)-2-((S)-1-Benzoylamino-1-carboxy-ethyl)-cyclopropanecarboxylic acid
  参考文献：
  名称：

  Synthesis of (2S,1′ S,2′ S)-2-methyl-2-(carboxycyclopropyl)glycine and (S)-2-amino-2-methyl-4-phosphonobutyric acid from l-alanine

  摘要：

  DOI：

  10.1016/s0957-4166(97)00031-1
• 作为产物：
  描述：

  L-丙氨酸 生成 (2R,4S)-3-苯甲酰基-4-甲基-2-苯基-1,3-恶唑烷-5-酮
  参考文献：
  名称：

  Stereoselective synthesis of isovaline (IVA) and IVA-containing dipeptldes for use in peptide synthesis 1

  摘要：

  DOI：

  10.1016/s0040-4020(01)86182-2

文献信息

• Enantioselective [1,2]-Stevens Rearrangement Using Sugar-Derived Alkoxides as Chiral Promoters
  作者：Katsuhiko Tomooka、Junichiro Sakamaki、Manabu Harada、Ryoji Wada

  DOI：10.1055/s-2008-1032107

  日期：——

  The first example of enantioselective base-induced [1,2]-Stevens rearrangement was achieved by using the newly developed D-glucose-derived lithium alkoxide as a chiral promoter. This rearrangement provides an α-amino ketone having a pseudoquaternary chiral center in an enantioenriched form.

  通过使用新开发的 D-葡萄糖衍生的醇锂作为手性促进剂，实现了对映选择性碱基诱导的 [1,2]-史蒂文斯重排的第一个例子。这种重排提供了具有对映体富集形式的假季铵手性中心的α-氨基酮。
• Flexible Synthesis and Evaluation of Diverse Anti-Apicomplexa Cyclic Peptides
  作者：Mariam Traoré、Flore Mietton、Danièle Maubon、Marine Peuchmaur、Flaviane Francisco Hilário、Rossimiriam Pereira de Freitas、Alexandre Bougdour、Aurélie Curt、Marjorie Maynadier、Henri Vial、Hervé Pelloux、Mohamed-Ali Hakimi、Yung-Sing Wong

  DOI：10.1021/jo4001492

  日期：2013.4.19

  A modular approach to synthesize anti-Apicomplexa parasite inhibitors was developed that takes advantage of a pluripotent cyclic tetrapeptide scaffold capable of adjusting appendage and skeletal diversities in only a few steps (one to three steps). The diversification processes make use of selective radical coupling reactions and involve a new example of a reductive carbon nitrogen cleavage reaction with SmI2. The resulting bioactive cyclic peptides have revealed new insights into structural factors that govern selectivity between Apicomplexa parasites such as Toxoplasma and Plasmodium and human cells.
• Synthesis of Optically Active Imidazolines, Azapenams, Dioxocyclams, and Bis-dioxocyclams
  作者：Yi Hsiao、Louis S. Hegedus

  DOI：10.1021/jo962343e

  日期：1997.5.1

  Optically active 4-methyl-4-carbomethoxy-Delta(2)-imidazoline was efficiently synthesized on a multigram scale. Photolysis with (methoxymethylcarbene)chromium complex produced the optically active azapenam in good yield and with high stereoselectivity. Acid-catalyzed dimerization followed by reduction produced the corresponding optically active dioxocyclam in good yield. Using a bis-carbene complex, an optically active bis-dioxocyclam was produced in excellent yield.
• Synthesis and biological evaluation of two analogues of (S)-α-methyl-3-carboxyphenylalanine
  作者：Dawei Ma、Zhaochun Ma、Alan P. Kozikowski、Sergey Pshenichkin、Jarda T. Wroblewski

  DOI：10.1016/s0960-894x(98)00409-0

  日期：1998.9

  Two analogues 2, 3 of (S)-alpha-methyl-3-carboxylphenylalanine 1 were synthesized to test their activity for metabotropic glutamate receptors (mGluRs). Both compounds 2 and 3 were inactive as antagonist for mGluRs, but 2 showed weak agonistic activity for GluR6 in contrast to that reported by Kemp and co-workers.
• FADEL, A.;SALAUN, J., TETRAHEDRON LETT., 28,(1987) N 20, 2243-2246
  作者：FADEL, A.、SALAUN, J.

  DOI：——

  日期：——