6-phenyl-2-(3-phenylaziridin-2-yl)-3-oxa-1-azabicyclo[3.1.0]hexan-4-ol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 6-phenyl-2-(3-phenylaziridin-2-yl)-3-oxa-1-azabicyclo[3.1.0]hexan-4-ol
• 英文别名: Rel-(2R,4R,5S,6R)-6-Phenyl-2-[(2R,3S)-3-phenyl-2-aziridinyl]-3-oxa-1-azabicyclo[3.1.0]hexan-4-ol；(2R,4R,5S,6R)-6-phenyl-2-[(2S,3R)-3-phenylaziridin-2-yl]-3-oxa-1-azabicyclo[3.1.0]hexan-4-ol
• 化学式: C₁₈H₁₈N₂O₂
• 分子量: 294.353
• InChiKey: GLGAFLIVZSLLEI-WCBNWKOVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  54.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-phenyl-2-(3-phenylaziridin-2-yl)-3-oxa-1-azabicyclo[3.1.0]hexan-4-ol 在 potassium carbonate 、 9-硼双环[3.3.1]壬烷 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 8.0h， 生成 phenyl-1 amino-1 butadiene-2,3
  参考文献：
  名称：

  基于应变的炔丙基胺的多功能合成平台

  摘要：

  不同的反应性：各种乙炔基氮丙啶表现为应变的炔丙基胺，可通过高度非对映选择性的S N 2'氢化物传输直接转化为未保护的α-氨基丙二烯（参见方案）。其他反应途径包括化学和区域选择性转化为双环氮丙啶/烯醇醚或高度紧张的叠氮炔。

  DOI：

  10.1002/anie.200906066
• 作为产物：
  描述：

  3-苯基环氧乙烷甲酸乙酯 在 sodium azide 、 ammonium chloride 、 二异丁基氢化铝 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 11.0h， 生成 6-phenyl-2-(3-phenylaziridin-2-yl)-3-oxa-1-azabicyclo[3.1.0]hexan-4-ol
  参考文献：
  名称：

  Readily Available Unprotected Amino Aldehydes

  摘要：

  We report a new class of bench-stable compounds that contain seemingly incompatible functional groups: an aldehyde and an unprotected secondary amine. The thermodynamic driving force to undergo condensation between these two functionalities is offset by a high barrier imposed on this process by the aziridine ring strain. The resulting amino aldehydes exist as dimers and in the solid state. They are stable to epimerization and contain two orthogonal reaction centers, namely, an amine/aziridine and an aldehyde. Their ability to act as linchpins has been evaluated in complex heterocycle synthesis. For instance, pentacyclic frameworks can be made in one simple operation using N-benzyltryptamine as the reaction partner. Construction of other molecular skeletons with minimal use of protecting group manipulations should be feasible.

  DOI：

  10.1021/ja065898s

文献信息

• Unprotected Vinyl Aziridines: Facile Synthesis and Cascade Transformations
  作者：Sivaraj Baktharaman、Nicholas Afagh、Adelle Vandersteen、Andrei K. Yudin

  DOI：10.1021/ol902550q

  日期：2010.1.15

  have led to the construction of a variety of stereochemically rich heterobicycles. A cascade ring-opening/ring-contraction mechanism operates in the course of the process. These results underscore the notion that interesting and useful nitrogen-mediated relay processes can arise when elements of strain are merged with the manifolds of enamine/iminium ion reactivity.

  易于从水稳定的氮丙啶醛获得的官能化乙烯基氮丙啶导致了多种立体化学丰富的杂环的构建。在该过程中，级联的开环/缩环机构起作用。这些结果强调了这样的观点，即当应变元素与烯胺/亚胺离子反应性的流形合并时，可能会出现有趣且有用的氮介导的中继过程。
• Skeletal Fusion of Small Heterocycles with Amphoteric Molecules
  作者：Lawrence L. W. Cheung、Zhi He、Shannon M. Decker、Andrei K. Yudin

  DOI：10.1002/anie.201106024

  日期：2011.12.2

  three contiguous stereocenters was prepared from a [3+2] annulation involving amphoteric aziridine aldehydes and isocyanates and further converted to a series of densely functionalized hetercycles, which are difficult to synthesize using established methods. The results highlight the potential of (1,3) amphoteric molecules to construct heterocyclic scaffolds using trivial starting materials.

  闩上：从涉及两性氮丙啶醛和异氰酸酯的[3 + 2]环合反应制得具有3个连续立体中心的新型乙内酰脲衍生物，并进一步转化为一系列致密官能化的杂环，这些杂环很难用既定方法合成。结果强调了（1,3）两性分子使用琐碎的起始原料构建杂环支架的潜力。
• WO2008/46232
  申请人：——

  公开号：——

  公开（公告）日：——
• Amphoteric Amino Aldehydes Enable Rapid Assembly of Unprotected Amino Alcohols
  作者：Ryan Hili、Andrei K. Yudin

  DOI：10.1002/anie.200705776

  日期：2008.5.19
• Readily Available Unprotected Amino Aldehydes
  作者：Ryan Hili、Andrei K. Yudin

  DOI：10.1021/ja065898s

  日期：2006.11.1

  We report a new class of bench-stable compounds that contain seemingly incompatible functional groups: an aldehyde and an unprotected secondary amine. The thermodynamic driving force to undergo condensation between these two functionalities is offset by a high barrier imposed on this process by the aziridine ring strain. The resulting amino aldehydes exist as dimers and in the solid state. They are stable to epimerization and contain two orthogonal reaction centers, namely, an amine/aziridine and an aldehyde. Their ability to act as linchpins has been evaluated in complex heterocycle synthesis. For instance, pentacyclic frameworks can be made in one simple operation using N-benzyltryptamine as the reaction partner. Construction of other molecular skeletons with minimal use of protecting group manipulations should be feasible.