(cis-2,3-diphenylaziridin-1-yl)(pyridin-2-yl)methanone | 1443674-19-8

• 分子结构分类: 有机化合物
• 英文名称: (cis-2,3-diphenylaziridin-1-yl)(pyridin-2-yl)methanone
• CAS: 1443674-19-8
• 化学式: C₂₀H₁₆N₂O
• 分子量: 300.36
• InChiKey: UCKRPORJJFBGLS-QIDMFYOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.02
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  32.97
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (cis-2,3-diphenylaziridin-1-yl)(pyridin-2-yl)methanone 在 tetrakis(dimethylamido)titanium(IV) 、 六氟异丙醇 、 苯甲酰氟 、 (R,R)-(salen)Co(III)OCH(CF₃)₂·HFIP 作用下， 以 甲基叔丁基醚 为溶剂， 反应 48.0h， 以48%的产率得到
  参考文献：
  名称：

  Enantioselective fluoride ring opening of aziridines enabled by cooperative Lewis acid catalysis

  摘要：

  The enantioselective ring opening of aziridines using a latent source of HF is described. A combination of two Lewis acids, (salen)Co and an achiral Ti(IV) cocatalyst, provided optimal reactivity and enantioselectivity for the trans beta-fluoroamine product. The use of a chelating aziridine protecting group was crucial. Acyclic and cyclic meso N-picolinamide aziridines underwent fluoride ring opening in up to 84% ee, and the kinetic resolution of a piperidine-derived aziridine was performed with k(rel)=6.6. The picolinamide group may be readily removed without epimerization of the fluoroamine. Preliminary studies revealed a bimetallic mechanism wherein the chiral (salen)Co catalyst delivers the nucleophile and the Ti(IV) cocatalyst activates the aziridine. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.01.062
• 作为产物：
  描述：

  2-吡啶甲酸 、 cis-2,3-diphenylaziridine 在 4-二甲氨基吡啶 、 N,N'-二异丙基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 (cis-2,3-diphenylaziridin-1-yl)(pyridin-2-yl)methanone
  参考文献：
  名称：

  Enantioselective fluoride ring opening of aziridines enabled by cooperative Lewis acid catalysis

  摘要：

  The enantioselective ring opening of aziridines using a latent source of HF is described. A combination of two Lewis acids, (salen)Co and an achiral Ti(IV) cocatalyst, provided optimal reactivity and enantioselectivity for the trans beta-fluoroamine product. The use of a chelating aziridine protecting group was crucial. Acyclic and cyclic meso N-picolinamide aziridines underwent fluoride ring opening in up to 84% ee, and the kinetic resolution of a piperidine-derived aziridine was performed with k(rel)=6.6. The picolinamide group may be readily removed without epimerization of the fluoroamine. Preliminary studies revealed a bimetallic mechanism wherein the chiral (salen)Co catalyst delivers the nucleophile and the Ti(IV) cocatalyst activates the aziridine. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.01.062

文献信息

• Intermolecular Enantioselective Dearomatization Reaction of β-Naphthol Using<i>meso</i>-Aziridine: A Bifunctional In Situ Generated Magnesium Catalyst
  作者：Dongxu Yang、Linqing Wang、Fengxia Han、Dan Li、Depeng Zhao、Rui Wang

  DOI：10.1002/anie.201410257

  日期：2015.2.9

  A direct, facile, and highly diastereo‐ and enantioselective dearomatization reaction of β‐naphthol derivatives with aziridines has been developed for the first time. A newly designed Box–OH ligand was employed for an in situ generated magnesium catalyst and proved to be efficient. The corresponding dearomatization product was transformed into a polycyclic scaffold and polyhydroxylated compound. 1H NMR

  β-萘酚衍生物与氮丙啶的直接，简便，高度非对映和对映选择性脱芳香化反应已得到首次开发。一种新设计的Box-OH配体用于原位生成的镁催化剂，并被证明是有效的。将相应的脱芳香化产物转化成多环支架和多羟基化的化合物。1 H NMR研究揭示了β-萘酚脱芳香化过程的活化模式，并且在反应中观察到明显的正非线性效应，并提供了对Mg II中心周围的配位环境和可能的活性物质的见解。
• Diversiform Reactivity of Naphthols in Asymmetric Dearomatization or O-Alkylation Reactions with Aziridines
  作者：Linqing Wang、Dongxu Yang、Dan Li、Haiyong Zhu、Pengxin Wang、Xihong Liu、Lutao Bai、Rui Wang

  DOI：10.1002/adsc.201801041

  日期：2018.12.3

  Here, we present a catalytic asymmetric and site‐selective reaction of naphthols, realizing diversiform reactions in asymmetric dearomatization or O‐alkylation with aziridines, and the reason for the switchable reactivity is formally analyzed with different type of substrates under different conditions.

  在这里，我们提出了萘酚的催化不对称和位点选择性反应，实现了在不对称脱芳烃化或O-烷基化反应中氮丙啶的多样化反应，并在不同条件下用不同类型的底物正式分析了可切换反应性的原因。
• Catalytic Desymmetrization of <i>meso</i>-Aziridines with Benzofuran-2(3<i>H</i>)-Ones Employing a Simple In Situ-Generated Magnesium Catalyst
  作者：Dan Li、Linqing Wang、Dongxu Yang、Bangzhi Zhang、Rui Wang

  DOI：10.1021/acscatal.5b02177

  日期：2015.12.4

  The first example of catalytic desymmetrization of meso-aziridines with benzofuran-2(3H) -ones is realized by employing a magnesium catalyst utilizing BINOL as a simple and commercially available chiral ligand. Both of the enantiomers of the ring-opening product could be easily accessed by employing (R)- or (S)-BINOL as chiral ligand, respectively. A variety of enantioenriched 3,3disubstituted benzofuran-2(3H)-ones containing multiple linear continuous stereocenters were obtained with moderate to good yields, diastereo- and enantioselectivities.