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

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: cis-1-(3,5-dinitrobenzoyl)-2,3-diphenylaziridine
• 英文别名: (3,5-dinitrophenyl)-[(2R,3S)-2,3-diphenylaziridin-1-yl]methanone
• 化学式: C₂₁H₁₅N₃O₅
• 分子量: 389.367
• InChiKey: WTLYURQADLLNFO-RLAPIPATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 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-diphenylaziridine 、 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 1.5h， 以98%的产率得到1-phenylthio-2-[N-(3,5-dinitrobenzoyl)amino]-1,2-diphenylethane
  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）。
• Guanidine-catalyzed enantioselective desymmetrization of meso-aziridines
  作者：Yan Zhang、Choon Wee Kee、Richmond Lee、Xiao Fu、Julian Ying-Teck Soh、Esther Mun Foong Loh、Kuo-Wei Huang、Choon-Hong Tan

  DOI：10.1039/c0cc05840h

  日期：——

  An amino-indanol derived chiral guanidine was developed as an efficient Brønsted base catalyst for the desymmetrization of meso-aziridines with both thiols and carbamodithioic acids as nucleophiles, which provided 1,2-difunctionalized ring-opened products in high yields and enantioselectivities.

  一种氨基-吲哚衍生的手性胍被开发作为高效的Brønsted碱催化剂，用于与硫醇和氨基二硫酸作为核苷酸的meso-亚胺环的去对称化，提供高产率和对映选择性的1,2-双功能化开环产物。
• Catalytic Enantioselective Ring-Opening Reaction of<i>meso</i>-Aziridines with α-Isothiocyanato Imides
  作者：Yi-Ming Cao、Fu-Ting Zhang、Fang-Fang Shen、Rui Wang

  DOI：10.1002/chem.201300297

  日期：2013.7.15

  Open up your chemistry! By using cinchonine‐based trimeric quaternary ammonium salts as catalysts, meso‐aziridines can be ring‐opened, in an enantioselective manner, through nucleophilic addition of the sulfur atom of α‐isothiocyanato imides (see scheme; PG=protecting group). This synthetic method provides an efficient way to access useful chiral β‐aminothiooxazole compounds.

  打开你的化学！通过使用基于辛可宁的三聚体季铵盐作为催化剂，可以通过亲核加成α-异硫氰酸根酰亚胺的硫原子，以对映选择性的方式将内消旋氮丙啶开环（参见方案; PG =保护基）。这种合成方法提供了一种有效的途径来获得有用的手性β-氨基硫恶唑化合物。
• 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.
• Highly Enantioselective Synthesis of β-Amidophenylthioethers by Organocatalytic Desymmetrization of <i>meso</i>-Aziridines
  作者：Giorgio Della Sala、Alessandra Lattanzi

  DOI：10.1021/ol901209n

  日期：2009.8.6

  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.