(4R,6S)-4,6-diphenyl-1,3-oxazinan-2-one | 87060-83-1

• 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: (4R,6S)-4,6-diphenyl-1,3-oxazinan-2-one
• 英文别名: (4R,6S)-4,6-Diphenyl-1,3-oxazinan-2-one
• CAS: 87060-83-1
• 化学式: C₁₆H₁₅NO₂
• 分子量: 253.301
• InChiKey: ICLIVROEGIIXAJ-CABCVRRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (R_S,1R,3S)-2-methylpropane-2-sulfinic acid (3-hydroxy-1,3-diphenylpropyl)amide 在 盐酸 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 2.0h， 以32%的产率得到(4R,6S)-4,6-diphenyl-1,3-oxazinan-2-one
  参考文献：
  名称：

  Asymmetric Synthesis of syn- and anti-1,3-Amino Alcohols

  摘要：

  The first application of metalloenamines derived from N-sulfinyl imines is reported for the highly diastereoselective addition to aldehydes. Reduction of the beta-hydroxy-N-sulfinyl imine products with catecholborane and LiBHEt3 provides syn- and anti-1,3-amino alcohol derivatives, respectively, with very high diastereomeric ratios.

  DOI：

  10.1021/ja026292g

文献信息

• Enantioselective Cycloaddition of Styrenes with Aldimines Catalyzed by a Chiral Magnesium Potassium Binaphthyldisulfonate Cluster as a Chiral Brønsted Acid Catalyst
  作者：Manabu Hatano、Keisuke Nishikawa、Kazuaki Ishihara

  DOI：10.1021/jacs.7b04795

  日期：2017.6.28

  A chiral magnesium potassium binaphthyldisulfonate cluster, as a chiral Brønsted acid catalyst, was shown to catalyze an enantioselective cycloaddition of styrenes with aldimines for the first time. The strong Brønsted acidity of the catalyst precursors, which might dissolve drying agents and take up the leached Mg2+ and K+, serendipitously led to good enantioselectivity. Mechanistic aspects were supported

  手性双萘基二磺酸镁钾盐簇，作为手性布朗斯台德酸催化剂，首次显示出与醛亚胺催化苯乙烯的对映选择性环加成反应。催化剂前体的强布朗斯台德酸度可能会溶解干燥剂并吸收浸出的Mg 2+和K +，从而偶然产生了良好的对映选择性。催化剂的X射线和ESI-MS分析以及反应动力学研究为力学方面提供了支持。还证实了以克为单位的向光学活性的1，3-氨基醇的有用转化。
• Asymmetric Synthesis of <i>s</i><i>yn</i>- and <i>a</i><i>nti</i>-1,3-Amino Alcohols
  作者：Takuya Kochi、Tony P. Tang、Jonathan A. Ellman

  DOI：10.1021/ja026292g

  日期：2002.6.1

  The first application of metalloenamines derived from N-sulfinyl imines is reported for the highly diastereoselective addition to aldehydes. Reduction of the beta-hydroxy-N-sulfinyl imine products with catecholborane and LiBHEt3 provides syn- and anti-1,3-amino alcohol derivatives, respectively, with very high diastereomeric ratios.