3-(3-phenylpentanoyl)oxazolidin-2-one | 123492-68-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(3-phenylpentanoyl)oxazolidin-2-one
• 英文别名: 1-(3-phenylpentanoyl)-2-oxazolidone；3-(3-Phenylpentanoyl)-1,3-oxazolidin-2-one；3-(3-phenylpentanoyl)-1,3-oxazolidin-2-one
• CAS: 123492-68-2
• 化学式: C₁₄H₁₇NO₃
• 分子量: 247.294
• InChiKey: IULAELNMBQPJTF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-苯基戊酸 在 正丁基锂 、 氯化亚砜 作用下， 以 四氢呋喃 为溶剂， 反应 38.0h， 生成 3-(3-phenylpentanoyl)oxazolidin-2-one
  参考文献：
  名称：

  Enantioselective conjugate radical addition reactions mediated by chiral Lewis acid complexes of (R,R)-4,6-dibenzofurandiyl-2,2′-bis(4-phenyloxazoline) (DBFOX/Ph)

  摘要：

  A high-yielding synthesis (50% overall yield) of tridentate bisoxazoline ligand (R,R)-4,6-dibenzofurandiyl-2,2'-bis(4-phenyloxazoline) (DBFOX/Ph) was developed. DBFOX/Ph was subsequently tested in enantioselective conjugate radical additions onto 3-(3-phenyl-2-propenoyl)-2-oxazolidinone Two dozen Lewis acids were evaluated, and Mg(ClO4)(2) emerged as the best Lewis acid in terms of yield and enantioselectivity (100% yield, 75.4% ee (S)). (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00238-4

文献信息

• Acyclic Diastereoselection in Prochiral Radical Addition to Prochiral Olefins
  作者：Mukund P. Sibi、Tara R. Rheault、Sithamalli V. Chandramouli、Craig P. Jasperse

  DOI：10.1021/ja017510t

  日期：2002.3.1

  reactive halogenated radicals (6f,g) (>15:1 anti). Steric influence in alkyl radical additions was difficult to evaluate due to decreased reactivity when using bulky reaction partners; however, more reactive alpha-alkoxy radicals, it was found that increasing steric bulk leads to moderate increases in selectivity. In addition, higher selectivity was observed when employing lanthanide Lewis acids whose environment

  当前手性自由基添加到前手性受体时，立体化学偏好（syn 或 anti）具有重要意义。这项研究的主要重点是确定哪些因素会影响同时形成的 β 和 γ 手性中心之间的相对立体化学。虽然发现将烷基 (6a-d) 和 α-烷氧基自由基 (16a-c)（< 或 = 6:1 syn）添加到受体 4、7、8、10 和 14 具有中等的非对映选择性，但始终具有高选择性观察到活性较低的卤化自由基 (6f,g) (>15:1 anti)。由于使用庞大的反应伙伴时反应性降低，因此难以评估烷基自由基加成中的空间影响；然而，对于更具反应性的 α-烷氧基自由基，发现增加空间体积会导致选择性适度增加。此外，当使用镧系路易斯酸时观察到更高的选择性，其环境（反应性）使用非手性添加剂进行了改变，这表明在自由基反应中提高选择性是一种潜在的简单方法。总的来说，这些结果表明显着的立体电子效应对于在前手性受体上实现前手性自由基加成的高水平选择性是必要的。
• Kunz, Horst; Pees, Klaus Juergen, Journal of the Chemical Society. Perkin transactions I, 1989, p. 1168 - 1169
  作者：Kunz, Horst、Pees, Klaus Juergen

  DOI：——

  日期：——
• Enantioselective conjugate radical addition reactions mediated by chiral Lewis acid complexes of (R,R)-4,6-dibenzofurandiyl-2,2′-bis(4-phenyloxazoline) (DBFOX/Ph)
  作者：Ulrich Iserloh、Dennis P Curran、Shuji Kanemasa

  DOI：10.1016/s0957-4166(99)00238-4

  日期：1999.6

  A high-yielding synthesis (50% overall yield) of tridentate bisoxazoline ligand (R,R)-4,6-dibenzofurandiyl-2,2'-bis(4-phenyloxazoline) (DBFOX/Ph) was developed. DBFOX/Ph was subsequently tested in enantioselective conjugate radical additions onto 3-(3-phenyl-2-propenoyl)-2-oxazolidinone Two dozen Lewis acids were evaluated, and Mg(ClO4)(2) emerged as the best Lewis acid in terms of yield and enantioselectivity (100% yield, 75.4% ee (S)). (C) 1999 Elsevier Science Ltd. All rights reserved.