(2R,4R,5S,6R)-6-isobutyl-2-((2S,3R)-3-isobutylaziridin-2-yl)-3-oxa-1-azabicyclo[3.1.0]hexan-4-ol | 1195982-83-2

• 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: (2R,4R,5S,6R)-6-isobutyl-2-((2S,3R)-3-isobutylaziridin-2-yl)-3-oxa-1-azabicyclo[3.1.0]hexan-4-ol
• CAS: 1195982-83-2
• 化学式: C₁₄H₂₆N₂O₂
• 分子量: 254.373
• InChiKey: NNJKXCWYLAHQIX-VFTUYNSUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.15
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  54.41
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  L-天门冬氨酸 、 异氰酸叔丁酯 、 (2R,4R,5S,6R)-6-isobutyl-2-((2S,3R)-3-isobutylaziridin-2-yl)-3-oxa-1-azabicyclo[3.1.0]hexan-4-ol 以 六氟异丙醇 为溶剂， 反应 3.0h， 以76%的产率得到2-((3S,5R,6R,7R)-5-(tert-butylcarbamoyl)-7-isobutyl-2-oxo-1,4-diazabicyclo[4.1.0]heptan-3-yl)acetic acid
  参考文献：
  名称：

  Hili, Ryan; Rai, Vishal; Yudin, Andrei K., Journal of the American Chemical Society, 2010, vol. 132, p. 2889 - 2891

  摘要：

  DOI：
• 作为产物：
  描述：

  在 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 反应 2.0h， 生成 (2R,4R,5S,6R)-6-isobutyl-2-((2S,3R)-3-isobutylaziridin-2-yl)-3-oxa-1-azabicyclo[3.1.0]hexan-4-ol
  参考文献：
  名称：

  半胺驱动催化微环境对炔基锌试剂的活化

  摘要：

  1,2-氮丙啶炔丙胺是通过锌催化的多组分反应获得的。该过程依赖于二聚氨基醛组装，协调分子内 1,2-炔与亚胺离子的加成。所得产物可以通过区域选择性氮丙啶开环轻松加工。提出了高度抗选择性炔烃加成的催化循环和立体化学原理。

  DOI：

  10.1002/ejoc.201601554

文献信息

• Synthesis of Chiral Piperazinones Using Amphoteric Aziridine Aldehyde Dimers and Functionalized Isocyanides
  作者：Niklas B. Heine、Sherif J. Kaldas、Lee Belding、Olga Shmatova、Travis Dudding、Valentine G. Nenajdenko、Armido Studer、Andrei K. Yudin

  DOI：10.1021/acs.joc.6b00471

  日期：2016.6.17

  functionalized isocyanides in the aziridine aldehyde-driven multicomponent synthesis of piperazinones. High diasteroselectivity for each isocyanide was observed. A theoretical evaluation of the reaction course corroborates the experimental data. Moreover, the reactivity of cis- and trans-configured aziridine aldehyde dimers has been compared. This study further probes the dimer-driven mechanism of

  我们在哌嗪酮的氮丙啶醛驱动的多组分合成中评估了一系列官能化的异氰化物。观察到每种异氰酸酯的高非对映选择性。反应过程的理论评估证实了实验数据。此外，已经比较了顺式和反式氮丙啶醛二聚体的反应性。这项研究进一步探讨了二聚体驱动环化的机制，并能够有效地获得各种带有功能化侧链的手性哌嗪酮。
• Amphoteric Amino Aldehydes Reroute the Aza-Michael Reaction
  作者：Ryan Hili、Andrei K. Yudin

  DOI：10.1021/ja9072194

  日期：2009.11.18

  Amphoteric amino aldehydes, which exist as stable dimers, participate in an aza-Michael/aldol domino reaction with alpha,beta-unsaturated aldehydes to afford stable 1,5-aminohydroxyaldehydes in high yields and diastereoselectivies. The reaction outcome hinges upon the dimeric nature of amphoteric amino aldehydes and the orthogonality between the NH aziridine and the two aldehyde functionalities during the reaction. Through the use of reaction conditions that disfavor dimer dissociation, the aza-Michael process has been directed toward a novel 8-(enolendo)-exo-trig cyclization. The results described herein further demonstrate the potential of amphoteric molecules in reaction discovery.
• Stereocontrolled Disruption of the Ugi Reaction toward the Production of Chiral Piperazinones: Substrate Scope and Process Development
  作者：Serge Zaretsky、Shinya Adachi、Benjamin H. Rotstein、Jennifer L. Hickey、Conor C. G. Scully、Jeffrey D. St. Denis、Rebecca Courtemanche、Joy C. Y. Yu、Benjamin K. W. Chung、Andrei K. Yudin

  DOI：10.1021/jo5018316

  日期：2014.11.7

  The factors determining diastereoselectivity observed in the multicomponent conversion of amino acids, aziridine aldehyde dimers, and isocyanides into chiral piperazinones have been investigated. Amino acid-dependent selectivity for either trans- or cis-substituted piperazinone products has been achieved. An experimentally determined diastereoselectivity model for the three-component reaction driven by aziridine aldehyde dimers has predictive value for different substrate classes. Moreover, this model is useful in reconciling the previously reported observations in multicomponent reactions between isocyanides, alpha-amino acids, and monofunctional aldehydes.