(R)-(-)-ethyl 4-phenyl-3-oxazolidineacetate | 150180-17-9

• 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: (R)-(-)-ethyl 4-phenyl-3-oxazolidineacetate
• 英文别名: (4R)-N-(ethoxycarbonylmethyl)-4-phenyloxazolidine；ethyl 2-[(4R)-4-phenyl-1,3-oxazolidin-3-yl]acetate
• CAS: 150180-17-9
• 化学式: C₁₃H₁₇NO₃
• 分子量: 235.283
• InChiKey: UFCPPLLSWJEDCT-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-(-)-ethyl 4-phenyl-3-oxazolidineacetate 在 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 一氧化碳 、 氢气 、 potassium iodide 作用下， 以 甲苯 为溶剂， 100.0 ℃ 、1.01 MPa 条件下， 反应 15.0h， 以97%的产率得到(5R)-4-methyl-5-phenylmorpholin-2-one
  参考文献：
  名称：

  Synthesis of Morpholin-2-ones by Chemoselective Intramolecular Rhodium-Catalyzed Reductive Ring Expansion of Oxazolidines

  摘要：

  The rhodium-catalyzed reductive intramolecular ring expansion of N-(ethoxycarboxymethyl)oxazolidines was carried out under an atmosphere of carbon monoxide and hydrogen to afford N-methylmorpholin-2-ones in good to excellent yields.

  DOI：

  10.1021/ol703135w
• 作为产物：
  描述：

  聚合甲醛 、 ((R)-2-Hydroxy-1-phenyl-ethylamino)-acetic acid ethyl ester 以 甲苯 为溶剂， 反应 5.0h， 生成 (R)-(-)-ethyl 4-phenyl-3-oxazolidineacetate
  参考文献：
  名称：

  Synthesis of Morpholin-2-ones by Chemoselective Intramolecular Rhodium-Catalyzed Reductive Ring Expansion of Oxazolidines

  摘要：

  The rhodium-catalyzed reductive intramolecular ring expansion of N-(ethoxycarboxymethyl)oxazolidines was carried out under an atmosphere of carbon monoxide and hydrogen to afford N-methylmorpholin-2-ones in good to excellent yields.

  DOI：

  10.1021/ol703135w

文献信息

• Regio- and stereoselective reduction of bicyclic imides for the asymmetric synthesis of highly substituted pyrrolidines
  作者：Pierre Deprez、Jacques Royer、Henri-Philippe Husson

  DOI：10.1016/s0040-4020(01)90230-3

  日期：1993.4

  cycloaddition of N-phenylmaleimide with azomethine ylides generated from α-aminonitrile or α-aminoester oxazolidines gave bicyclic imides, which were reduced regio- and stereoselectively to hydroxylactams. In the aminonitrile series, reduction with NaBH4/CeCl3 at low temperature gave a single hydroxylactam in high yield. In the aminoester series the regioselectivity was more dependent on the structure, and

  N-苯基马来酰亚胺的1，3-偶极环加成反应与由α-氨基腈或α-氨基酯恶唑烷生成的甲亚胺基团产生双环酰亚胺，其区域和立体选择性还原为羟基内酰胺。在氨基腈系列中，在低温下用NaBH 4 / CeCl 3还原可得到高产率的单一羟基内酰胺。在氨基酯系列中，区域选择性更多地取决于结构，并且发现其他条件（LiBEt 3 H）获得的单个羟基内酰胺与氨基腈系列相比对应于反向区域化学。
• Synthesis of Morpholin-2-ones by Chemoselective Intramolecular Rhodium-Catalyzed Reductive Ring Expansion of Oxazolidines
  作者：Maksym Vasylyev、Howard Alper

  DOI：10.1021/ol703135w

  日期：2008.4.1

  The rhodium-catalyzed reductive intramolecular ring expansion of N-(ethoxycarboxymethyl)oxazolidines was carried out under an atmosphere of carbon monoxide and hydrogen to afford N-methylmorpholin-2-ones in good to excellent yields.