4(R*)-<(S*)-hydroxy(phenyl)methyl>-1,3-oxazolin-2-one | 129217-19-2

• 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: 4(R*)-<(S*)-hydroxy(phenyl)methyl>-1,3-oxazolin-2-one
• 英文别名: 4(R*)-[(S*)-hydroxy(phenyl)methyl]-1,3-oxazolin-2-one；(4S)-4-[(R)-hydroxy(phenyl)methyl]-1,3-oxazolidin-2-one
• CAS: 129217-19-2
• 化学式: C₁₀H₁₁NO₃
• 分子量: 193.202
• InChiKey: NHYAJYRAUVMWNS-DTWKUNHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4(R*)-<(S*)-hydroxy(phenyl)methyl>-1,3-oxazolin-2-one 在 palladium on activated charcoal 4-二甲氨基吡啶 、 sodium azide 、 氢气 、 caesium carbonate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 38.5h， 生成 2(R),3(S)-2-benzoylamino-2-(tert-butyloxycarbonyl)amino-3-phenyl-propan-1-ol
  参考文献：
  名称：

  2,3-二氨基酸的制备：紫杉醇侧链胺化类似物的立体控制合成

  摘要：

  提出了一种制备2，3-二氨基酸的方法，并将其用于合成紫杉醇侧链的类似物β-苯甲酰基氨基-苯丙氨酸（2b）。由常见的旋光活性前体制备得到不同保护的赤型和苏式二胺。

  DOI：

  10.1016/0040-4020(96)00562-5
• 作为产物：
  描述：

  1-苯基-2-丙烯-1-醇 在 lithium hydroxide 、 sodium hydride 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 四氯化碳 、 二氯甲烷 、 水 为溶剂， 生成 4(R*)-<(S*)-hydroxy(phenyl)methyl>-1,3-oxazolin-2-one
  参考文献：
  名称：

  N-benzoylcarbamate cyclizations

  摘要：

  DOI：

  10.1016/s0040-4039(00)96738-8

文献信息

• The regioselective aminohydroxylation of allylic carbamates
  作者：Timothy J. Donohoe、Peter D. Johnson、Madeleine Helliwell、Martine Keenan

  DOI：10.1039/b107253f

  日期：2001.10.11

  The synthesis and aminohydroxylation of a series of acyclic allylic carbamates is described: the formation of a putative OOsNR linkage between the transition metal and substrate is proposed to account for the high levels of regioselectivity that were observed; proof of the structure of one of the aminohydroxylation products was obtained through X-ray crystallography.

  介绍了一系列无环烯丙基氨基甲酸酯的合成和氨基羟基化过程：过渡金属和底物之间形成了一种假定的 OOsNR 连接，这就是所观察到的高水平区域选择性的原因；通过 X 射线晶体学，证明了其中一种氨基羟基化产物的结构。
• Iron(II)-Catalyzed Intramolecular Aminohydroxylation of Olefins with Functionalized Hydroxylamines
  作者：Guan-Sai Liu、Yong-Qiang Zhang、Yong-An Yuan、Hao Xu

  DOI：10.1021/ja311923z

  日期：2013.3.6

  A diastereoselective aminohydroxylation of olefins with a functionalized hydroxylamine is catalyzed by new iron(II) complexes. This efficient intramolecular process readily affords synthetically useful amino alcohols with excellent selectivity (dr up to > 20:1). Asymmetric catalysis with chiral iron(II) complexes and preliminary mechanistic studies reveal an iron nitrenoid is a possible intermediate that can undergo either aminohydroxylation or aziridination, and the selectivity can be controlled by careful selection of counteranion/ligand combinations.
• Amino alcohol and amino sugar synthesis by benzoylcarbamate cyclization
  作者：Spencer Knapp、Paivi J. Kukkola、Shashi Sharma、T. G. Murali Dhar、Andrew B. J. Naughton

  DOI：10.1021/jo00309a013

  日期：1990.10
• Diastereoselective synthesis of substituted 2-amino-1,3-propanediols from Morita-Baylis-Hillman adducts
  作者：Paulo H. S. Paioti、Patrícia Rezende、Fernando Coelho

  DOI：10.1590/s0103-50532012000200014

  日期：——

  We report herein a new diastereoselective approach to substituted 2-amino-1,3-propanediols with anti relative stereochemistry from Morita-Baylis-Hillman (MBH) adducts. These structural moieties have been used as intermediates for the synthesis of several compounds with relevant pharmacological and commercial interest. In this strategy, substituted anti 2-amino-1,3-propanediols were readily prepared via ozonolysis of allylic diols obtained from MBH adducts, followed by a diastereoselective reductive amination of the substituted 2-oxo-1,3-propanediols. To demonstrate the synthetic utility of these aminodiols, they were transformed into substituted oxazolidin-2-ones, which were also used in the indirect determination of the relative stereochemistry of the aminodiols.