cis-1-(3,5-dinitrobenzoyl)-2,3-dipropylaziridine

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: cis-1-(3,5-dinitrobenzoyl)-2,3-dipropylaziridine
• 英文别名: (3,5-dinitrophenyl)-[(2S,3R)-2,3-dipropylaziridin-1-yl]methanone
• 化学式: C₁₅H₁₉N₃O₅
• 分子量: 321.333
• InChiKey: QQWXNWKLGHMDDO-MZBDJJRSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  112
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  cis-1-(3,5-dinitrobenzoyl)-2,3-dipropylaziridine 、 苯基硫三甲基硅烷 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 1.0h， 以94%的产率得到4-phenylthio-5-[N-(3,5-dinitrobenzoyl)amino]octane
  参考文献：
  名称：

  Highly Enantioselective Synthesis of β-Amidophenylthioethers by Organocatalytic Desymmetrization of meso-Aziridines

  摘要：

  The desymmetrization of N-acylaziridines with Me3SiSPh, catalyzed by commercially available (R) and (S)-VAPOL hydrogen phosphate, produced beta-(N-acylamino)phenylthioethers in a highly enantioselective and efficient manner (78-99% ee). The selection of the suitable aziridine/nucleophile/catalyst molar ratio is crucial to obtain high ee's.

  DOI：

  10.1021/ol901209n

文献信息

• A general phosphoric acid-catalyzed desymmetrization of meso-aziridines with silylated selenium nucleophiles
  作者：Matilde Senatore、Alessandra Lattanzi、Stefano Santoro、Claudio Santi、Giorgio Della Sala

  DOI：10.1039/c1ob05837a

  日期：——

  The first example of meso-aziridine desymmetrization with selenium nucleophiles is reported. The reaction, promoted by VAPOL-hydrogen phosphate using (phenylseleno)trimethylsilane as the nucleophile, proves to be very general and highly enantioselective (84–99% ee).

  首次报道了硒亲核试剂参与的中位氮杂环丙烷去对称化反应。该反应以VAPOL磷酸氢二钠为促进剂，采用（苯硒基）三甲基硅烷作为亲核试剂，其适用范围非常广泛，且具有高度的对映选择性（84-99% 对映体过量）。
• Chiral Phosphoric Acid-Catalyzed Desymmetrization of <i>meso</i>-Aziridines with Functionalized Mercaptans
  作者：Shawn E. Larson、Juan C. Baso、Guilong Li、Jon C. Antilla

  DOI：10.1021/ol902123h

  日期：2009.11.19

  Conditions for the phosphoric acid-catalyzed highly enantioselective ring-opening of meso-aziridines with a series of functionalized aromatic thiol nucleophiles are described. The procedure utilizes commercially available aromatic thiols, a series of meso-aziridines, and a catalytic amount of VAPOL phosphoric acid to explore the substrate scope of this highly enantioselective reaction.
• De Novo Synthesis of Tamiflu via a Catalytic Asymmetric Ring-Opening of <i>meso</i>-Aziridines with TMSN₃
  作者：Yuhei Fukuta、Tsuyoshi Mita、Nobuhisa Fukuda、Motomu Kanai、Masakatsu Shibasaki

  DOI：10.1021/ja061696k

  日期：2006.5.1

  An asymmetric ring-opening reaction of meso-aziridines with TMSN3 was developed using a catalyst prepared from Y(OiPr)3 and chiral ligand 2 in a 1:2 ratio. Excellent enantioselectivity was realized from a wide range of substrates with a practical catalyst loading. The products were efficiently converted to enantiomerically enriched 1,2-diamines, which are versatile chiral building blocks for pharmaceuticals and chiral ligands. This reaction was applied to a catalytic asymmetric synthesis of Tamiflu, a very important anti-influenza drug containing a chiral 1,2-diamino functionality.
• Catalytic Asymmetric Ring-Opening of<i>meso-</i>Aziridines with Malonates under Heterodinuclear Rare Earth Metal Schiff Base Catalysis
  作者：Yingjie Xu、Luqing Lin、Motomu Kanai、Shigeki Matsunaga、Masakatsu Shibasaki

  DOI：10.1021/ja201492x

  日期：2011.4.20

  Catalytic asymmetric ring-opening of meso-aziridines with malonates is described. The combined use of two rare earth metal sources with different properties promoted the desired ring-opening reaction. A 1:1:1 mixture of a heterobimetallic La(O-iPr)(3)/Yb(OTf)(3)/Schiff base la (0.25-10 mol %) efficiently promoted the reaction of five-, six-, and seven-membered ring cyclic meso-aziridines as well as acyclic meso-aziridines with dimethyl, diethyl, and dibenzyl malonates, giving chiral cyclic and acyclic gamma-amino esters in 99-63% yield and > 99.5-97% ee.
• Catalytic Enantioselective Desymmetrization of meso-Aziridines with Fluoromalonates
  作者：Shigeki Matsunaga、Seiya Fukagawa、Yingjie Xu、Masahiro Anada、Tatsuhiko Yoshino

  DOI：10.3987/com-17-13725

  日期：——

  Catalytic enantioselective desymmetrization of meso-aziridines with fluoromalonates is described. Optimization studies revealed that the appropriate combination of Bronsted basic metal and Lewis acidic metal is important for promoting the reaction using fluoromalonates. A heterodinuclear Gd(OiPr)(3)/Y(OTf)(3)/Schiff base = 1:1:1 was the best catalyst, and ring-opening adducts, synthetic precursors for alpha-fluoro-gamma-amino acids, were obtained in 98%similar to 17% yield and >99.5%similar to 99% ee. Transformation of the ring-opening adduct into alpha-fluoro-gamma-lactam was also demonstrated.