2-[2-(4-fluoro-phenyl)-aziridin-1-yl]-isoindole-1,3-dione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-[2-(4-fluoro-phenyl)-aziridin-1-yl]-isoindole-1,3-dione
• 英文别名: N-(aminophthalimide)-2-p-fluoro-phenylaziridine；2-[2-(4-Fluorophenyl)aziridin-1-yl]isoindole-1,3-dione
• 化学式: C₁₆H₁₁FN₂O₂
• 分子量: 282.274
• InChiKey: ISKGJIBEAIDVAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  40.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  溶剂黄146 、 2-[2-(4-fluoro-phenyl)-aziridin-1-yl]-isoindole-1,3-dione 以 二氯甲烷 为溶剂， 生成 2-((1,3-dioxoisoindolin-2-yl)amino)-1-(4-fluorophenyl)ethyl acetate
  参考文献：
  名称：

  一锅烯烃叠氮和酸环开环可无金属合成1,2-氨基醇

  摘要：

  已经开发了一种一锅两步反应，该反应包括烯烃叠氮化和氮丙啶中间体的开环以合成1,2-氨基醇。该反应适用于几种类型的烯烃。该方法学允许对各种1,2-氨基醇进行高效且高度立体选择性的方法，轻松为常规邻位氨基醇提供替代途径。

  DOI：

  10.1016/j.tetlet.2018.06.002
• 作为产物：
  描述：

  4-氟苯乙烯 、 氨基邻苯二甲胺 在 碘苯二乙酸 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以87%的产率得到2-[2-(4-fluoro-phenyl)-aziridin-1-yl]-isoindole-1,3-dione
  参考文献：
  名称：

  一锅烯烃叠氮和酸环开环可无金属合成1,2-氨基醇

  摘要：

  已经开发了一种一锅两步反应，该反应包括烯烃叠氮化和氮丙啶中间体的开环以合成1,2-氨基醇。该反应适用于几种类型的烯烃。该方法学允许对各种1,2-氨基醇进行高效且高度立体选择性的方法，轻松为常规邻位氨基醇提供替代途径。

  DOI：

  10.1016/j.tetlet.2018.06.002

文献信息

• Electrocatalytic Aziridination of Alkenes Mediated by <i>n</i>-Bu₄NI: A Radical Pathway
  作者：Jie Chen、Wei-Qing Yan、Chiu Marco Lam、Cheng-Chu Zeng、Li-Ming Hu、R. Daniel Little

  DOI：10.1021/acs.orglett.5b00083

  日期：2015.2.20

  Efficient electrocatalytic aziridination of alkenes has been achieved for the first time. A structurally broad range of aziridines was easily accessed using an undivided cell operated at constant current and mediated by a catalytic quantity of n-Bu4NI. The electrocatalytic reaction also proceeded in the absence of additional conducting salt. The aziridination is proposed to follow a radical mechanism.
• Aryl Iodide Mediated Aziridination of Alkenes
  作者：Jiayin Li、Philip Wai Hong Chan、Chi-Ming Che

  DOI：10.1021/ol052293c

  日期：2005.12.1

  Aryl iodide mediated aziridination of a variety of alkenes with N-aminophthalimide under mild conditions (m-CPBA, K(2)CO(3), CH(2)Cl(2), 25 degrees C) was achieved in moderate to good yields (up to 94%). By recovering the aryl iodide, a recyclable system is developed with product yield over 79% attained for the aziridination of trans-1,2-diphenylethylene.
• Aziridination of alkenes with N-substituted hydrazines mediated by iodobenzene diacetate
  作者：Jiayin Li、Jiang-Lin Liang、Philip Wai Hong Chan、Chi-Ming Che

  DOI：10.1016/j.tetlet.2004.01.127

  日期：2004.3

  Aziridination of a variety of alkenes with N-substituted hydrazines mediated by iodobenzene diacetate under mild conditions (K2CO3, CH2Cl2) and ambient temperature were achieved in good to excellent yields (up to 99%), and conversions. The practicality and simplicity of this C-N bond formation protocol was exemplified by its application to the aziridination of cholesteryl acetate in a stereoselective manner. (C) 2004 Elsevier Ltd. All rights reserved.
• Metal-free synthesis of 1,2-amino alcohols by one-pot olefin aziridination and acid ring-opening
  作者：Yong-Gang Hua、Qian-Qian Yang、Yi Yang、Mei-Jing Wang、Wen-Chao Chu、Peng-Yan Bai、De-Yun Cui、En Zhang、Hong-Min Liu

  DOI：10.1016/j.tetlet.2018.06.002

  日期：2018.7

  1,2-amino alcohols has been developed. This reaction is suitable for several types of olefin. This methodology allows an efficient and highly stereoselective approach to various 1,2-amino alcohols, readily providing an alternative route to conventional vicinal amino alcohols.

  已经开发了一种一锅两步反应，该反应包括烯烃叠氮化和氮丙啶中间体的开环以合成1,2-氨基醇。该反应适用于几种类型的烯烃。该方法学允许对各种1,2-氨基醇进行高效且高度立体选择性的方法，轻松为常规邻位氨基醇提供替代途径。