5-phenyl-2-(2-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: 5-phenyl-2-(2-phenylaziridin-2-yl)-3-oxa-1-azabicyclo[3.1.0]hexan-4-ol
• 英文别名: (2R,4R,5S)-5-phenyl-2-[(2S)-2-phenylaziridin-2-yl]-3-oxa-1-azabicyclo[3.1.0]hexan-4-ol
• 化学式: C₁₈H₁₈N₂O₂
• 分子量: 294.353
• InChiKey: FRMNOKKAYGDSPO-PCMBYBMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 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：

  5-phenyl-2-(2-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 2-phenylbuta-2,3-dien-1-amine
  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：

  苯乙酸甲酯 在 sodium azide 、 二异丁基氢化铝 、 氯化铵 、 间氯过氧苯甲酸 、 三苯基膦 作用下， 以 二氯甲烷 、 甲苯 、 乙腈 、 苯 为溶剂， 反应 9.0h， 生成 5-phenyl-2-(2-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

• 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.
• A Versatile Synthetic Platform Based on Strained Propargyl Amines
  作者：Zhi He、Andrei K. Yudin

  DOI：10.1002/anie.200906066

  日期：2010.2.22

  Divergent reactivity: Various ethynylaziridines behave as strained propargyl amines and can be directly converted into unprotected α‐amino allenes by a highly diastereoselective SN2′ hydride delivery (see scheme). Additional reaction routes involve chemo‐ and regioselective transformation into either bicyclic aziridine/enol ethers or highly strained azirine alkynes.

  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。