(2SR,6SR)-2,6-diphenyl-[1,3]oxazinan-4-one | 1384180-18-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: (2SR,6SR)-2,6-diphenyl-[1,3]oxazinan-4-one
• 英文别名: cis-2,6-diphenyl[1,3]oxazinan-4-one；(2R,6R)-2,6-diphenyl-1,3-oxazinan-4-one
• CAS: 1384180-18-0
• 化学式: C₁₆H₁₅NO₂
• 分子量: 253.301
• InChiKey: GYFMHRXQPIPBMT-GDBMZVCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.96
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  38.33
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (2SR,6SR)-2,6-diphenyl-[1,3]oxazinan-4-one 在 lithium aluminium tetrahydride 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 4.0h， 生成 2-(菲-2-基)乙酰氯
  参考文献：
  名称：

  5-Phenylthio-1,3-oxazinan-4-ones via hetero Diels–Alder reactions: synthesis of (R)- and (S)-Duloxetines and Fluoxetines

  摘要：

  The synthesis of 5-phenylthio-1,3-oxazinan-4-ones, through a hetero Diels-Alder strategy, is described. The cycloadducts thus prepared have been shown to be useful intermediates for the synthesis of 1,3-aminoalcohols, valuable intermediates in the preparation of biologically significant molecules, e.g., optically active Duloxetines and Fluoxetines. In the course of this elaboration a novel microwave assisted desulfurization reaction is reported. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.10.006
• 作为产物：
  描述：

  (2SR,5SR,6RS)-2,6-diphenyl-5-phenylthio-[1,3]oxazinan-4-one 在 镍 作用下， 以 乙醇 为溶剂， 反应 0.03h， 以80%的产率得到(2SR,6SR)-2,6-diphenyl-[1,3]oxazinan-4-one
  参考文献：
  名称：

  5-Phenylthio-1,3-oxazinan-4-ones via hetero Diels–Alder reactions: synthesis of (R)- and (S)-Duloxetines and Fluoxetines

  摘要：

  The synthesis of 5-phenylthio-1,3-oxazinan-4-ones, through a hetero Diels-Alder strategy, is described. The cycloadducts thus prepared have been shown to be useful intermediates for the synthesis of 1,3-aminoalcohols, valuable intermediates in the preparation of biologically significant molecules, e.g., optically active Duloxetines and Fluoxetines. In the course of this elaboration a novel microwave assisted desulfurization reaction is reported. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.10.006

文献信息

• Enantio- and diastereoselective hetero-Diels–Alder reactions between 2-aza-3-silyloxy-1,3-butadienes and aldehydes catalyzed by chiral dirhodium(ii) carboxamidates
  作者：Yudai Watanabe、Takuya Washio、Janagiraman Krishnamurthi、Masahiro Anada、Shunichi Hashimoto

  DOI：10.1039/c2cc32876c

  日期：——

  The first catalytic asymmetric hetero-Diels–Alder reaction between 2-aza-3-silyloxy-1,3-butadienes and aldehydes is described. With dirhodium(II) tetrakis[N-benzene-fused-phthaloyl-(S)-piperidinonate], Rh2(S-BPTPI)4, the cycloaddition reaction proceeded exclusively in an endo mode to give all-cis-substituted 1,3-oxazinan-4-ones in high yields with up to 98% ee.

  描述了一种首次催化不对称异核Diels–Alder反应，该反应涉及2-氮-3-硅氧基-1,3-丁二烯和醛。在二铑(II)四羧酸盐[N-苯基-融合邻苯二甲酰胺-(S)-哌啶酮]催化下，Rh2(S-BPTPI)4，环加成反应仅以内消旋的方式进行，获得了全顺-取代的1,3-氧杂哌嗪-4-酮，产率高达98%光学纯度。
• EuFOD-Catalyzed Hetero-Diels-Alder (HDA) Reaction under Microwave Heating
  作者：Mauro Panunzio、Elisa Bandini、Antonio D’Aurizio、Alessia Millemaggi、Zhining Xia

  DOI：10.1055/s-2007-965985

  日期：2007.7

  An efficient EuFOD-catalyzed hetero-Diels-Alder reaction between azadienes and aldehydes under microwave irradiation is reported. The reaction proceeds under microwave heating with 5 mol% of EuFOD in 45-83% yields.

  报道了一种在微波辐照下，使用EuFOD催化的高效杂源Diels-Alder反应，反应物为氮烯和醛。该反应在微波加热下进行，使用5 mol%的EuFOD，产率在45%至83%之间。