(5R)-5-Phenyl[1,3,4]oxadiazinan-2-one | 216569-16-3

• 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: (5R)-5-Phenyl[1,3,4]oxadiazinan-2-one
• 英文别名: (5R)-5-phenyl-1,3,4-oxadiazinan-2-one
• CAS: 216569-16-3
• 化学式: C₉H₁₀N₂O₂
• 分子量: 178.191
• InChiKey: QAGJKMIPZUAJKL-QMMMGPOBSA-N

物化性质

• 密度：
  1.185±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  50.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5R)-5-Phenyl[1,3,4]oxadiazinan-2-one 在 钯 硫酸 、 氢气 作用下， 以 甲醇 、 氯仿 、 甲苯 为溶剂， 反应 96.0h， 生成 (4R,6S,7S,8R)-6-cyclohexylethyl-1-oxo-4-phenyltetrahydropyrazolo[1,2-c][1,3,4]oxadiazine-7,8-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  Asymmetric Synthesis of Densely Functionalized Pyrazolidines and 1,3-Diamines

  摘要：

  本文介绍了一种多功能、直接获得多取代 1,3-二胺的方法，该方法能很好地控制相对构型和绝对构型。 其关键步骤包括手性非外消旋偶氮亚胺酰亚胺的非对映选择性 1,3-二极环加成，以及致密官能化吡唑烷中间体的化学选择性电还原。

  DOI：

  10.1055/s-2002-33914
• 作为产物：
  描述：

  (R)-(-)-N-苄基-2-苯甘氨醇 在 palladium dihydroxide 盐酸 、 lithium aluminium tetrahydride 、 氢气 、 sodium nitrite 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 水 为溶剂， -78.0~70.0 ℃ 、1000.0 kPa 条件下， 反应 92.0h， 生成 (5R)-5-Phenyl[1,3,4]oxadiazinan-2-one
  参考文献：
  名称：

  Preparation and diastereoselective functionalization of a new chiral non racemic bicyclic hydrazinolactam

  摘要：

  Starting with R-(-)-phenylglycinol, the synthesis of a new bicyclic hydrazinolactam 3 was realized on a multigram scale. The reaction scope of the corresponding enolate with various electrophiles has been studied. Good to excellent diastereoselectivities were obtained. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01813-9

文献信息

• Diastereoselective Cycloadditions of Chiral Non-racemic Azomethine Imines
  作者：Fanny Roussi、Ariane Chauveau、Martine Bonin、Laurent Micouin、Henri-Philippe Husson

  DOI：10.1055/s-2000-6311

  日期：——

  (5R)-5-Phenyl[1,3,4]oxadiazinan-2-one (6) is an easily available building block and acts as a chiral non-racemic precursor for azomethine imines. The ylid can be formed regioselectively with various aldehydes and reacts in an efficient manner with a wide range of dipolarophiles. The regio- and diastereoselectivity of the cycloadditions have been fully investigated and can lead, in the best cases, to the creation of three contiguous asymmetric centers in a single step, with complete control of relative and absolute configurations.

  (5R)-5-苯基[1,3,4]恶二嗪-2-酮（6）是一种易于获得的结构单元，可作为偶氮亚胺的手性非外显前体。该酰基可与各种醛发生区域选择性反应，并能与多种双极性化合物发生高效反应。我们已经对环化反应的区域和非对映选择性进行了充分研究，在最佳情况下，可以在一个步骤中生成三个连续的不对称中心，并完全控制相对和绝对构型。
• Asymmetric 1,3-dipolar cycloadditions of a chiral non-racemic azomethine imine
  作者：Fanny Roussi、Martine Bonin、Angèle Chiaroni、Laurent Micouin、Claude Riche、Henri-Philippe Husson

  DOI：10.1016/s0040-4039(99)00610-3

  日期：1999.5

  Chiral non racemic carbazate 1, derived from (R)-(−)-phenylglycinol, reacts regioselectively with benzaldehyde or its dimethylacetal to give an azomethine imine. The facial, and regio selectivities of 1,3-dipolar cycloadditions of this reactive species with various dipolarophiles have been studied and are described in this paper. In the best cases, up to three contiguous asymmetric centers could be

  衍生自（R）-（-）-苯基甘氨醇的手性非外消旋氨基甲酸酯1与苯甲醛或其二甲基缩醛区域选择性反应，生成偶氮甲亚胺。已经研究并描述了该反应性物种与各种偶极亲和性的1,3-偶极环加成反应的面部和区域选择性。在最佳情况下，最多可以同时以完整的对映和非对映选择性方式生成三个连续的不对称中心。
• Asymmetric 1,3-dipolar cycloadditions of a chiral nonracemic glyoxylic azomethine imine
  作者：Florence Chung、Ariane Chauveau、Mohamed Seltki、Martine Bonin、Laurent Micouin

  DOI：10.1016/j.tetlet.2004.02.088

  日期：2004.4

  The reactivity of a chiral nonracemic glyoxylic azomethine imine has been investigated. This species reacts with a wide range of dipolarophiles, with a complete regio- and facial stereoselectivity. The introduction of an electron-withdrawing substituent on the ylide leads to a lower endo selectivity with electron-withdrawing dipolarophiles, but to an improved exo selectivity with styrene derivatives when compared to the reactivity of aliphatic- or aromatic-substituted ylides. (C) 2004 Elsevier Ltd. All rights reserved.
• Preparation and diastereoselective functionalization of a new chiral non racemic bicyclic hydrazinolactam
  作者：Fanny Roussi、Martine Bonin、Angèle Chiaroni、Laurent Micouin、Claude Riche、Henri-Philippe Husson

  DOI：10.1016/s0040-4039(98)01813-9

  日期：1998.10

  Starting with R-(-)-phenylglycinol, the synthesis of a new bicyclic hydrazinolactam 3 was realized on a multigram scale. The reaction scope of the corresponding enolate with various electrophiles has been studied. Good to excellent diastereoselectivities were obtained. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.
• Asymmetric Synthesis of Densely Functionalized Pyrazolidines and 1,3-Diamines
  作者：M. Bonin、L. Micouin、A. Chauveau、T. Martens、H.-P. Husson

  DOI：10.1055/s-2002-33914

  日期：——

  A versatile and straightforward access to polysubstituted 1,3-diamines with good control of relative and absolute configurations is described. The key steps involve a diastereoselective 1,3-dipolar cycloaddition of a chiral non-racemic azomethine imine ylide and a chemoselective electroreduction of densely functionalized pyrazolidines intermediates.

  本文介绍了一种多功能、直接获得多取代 1,3-二胺的方法，该方法能很好地控制相对构型和绝对构型。 其关键步骤包括手性非外消旋偶氮亚胺酰亚胺的非对映选择性 1,3-二极环加成，以及致密官能化吡唑烷中间体的化学选择性电还原。