cis-1-(4-nitrobenzoyl)-2,3-diphenylaziridine | 7042-08-2

• 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: cis-1-(4-nitrobenzoyl)-2,3-diphenylaziridine
• 英文别名: p-nitrobenzoyl-cis-2,3-diphenylaziridine；1-(4-nitro-benzoyl)-2r,3c-diphenyl-aziridine；[(2S,3R)-2,3-diphenylaziridin-1-yl]-(4-nitrophenyl)methanone
• CAS: 7042-08-2
• 化学式: C₂₁H₁₆N₂O₃
• 分子量: 344.37
• InChiKey: SFVSPDCUCWCHAQ-RLAPIPATSA-N

物化性质

• 熔点：
  153-156 °C
• 沸点：
  546.2±50.0 °C(Predicted)
• 密度：
  1.316±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  26
• 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：
  65.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  cis-1-(4-nitrobenzoyl)-2,3-diphenylaziridine 以 xylene 为溶剂， 反应 48.0h， 生成 2-(4-nitro-phenyl)-4r,5c-diphenyl-4,5-dihydro-oxazole
  参考文献：
  名称：

  Aziridines. XVI. Isomerization of some 1-aroyl-aziridines

  摘要：

  DOI：

  10.1021/jo01285a030
• 作为产物：
  描述：

  4-硝基苯甲酰氯 、 cis-2,3-diphenylaziridine 在 三乙胺 作用下， 以 乙醚 为溶剂， 反应 15.0h， 以55%的产率得到cis-1-(4-nitrobenzoyl)-2,3-diphenylaziridine
  参考文献：
  名称：

  酒石酸二烷基酯-二乙基锌配合物催化对称的N-酰基氮丙啶与硫醇的不对称开环反应

  摘要：

  在由二乙基锌和L-（+）-酒石酸二烷基酯制备的手性锌络合物的存在下，进行1,2-（N-酰基亚氨基）环己烷（N-酰基环丙啶）与一些硫醇的不对称开环反应，得到反式2-（N-酰基氨基）-1-芳基硫代环己烷的ee最高可达93％。对映选择性很大程度上受反应物的摩尔比和手性酒石酸二烷基酯的性质的影响。L-（+）-酒石酸锌-二烷基络合物的化学结构通过1 H NMR光谱和分子量进行了讨论。

  DOI：

  10.1016/0040-4020(96)00370-5

文献信息

• Ru ^V ‐Acylimido Intermediate in [Ru ^IV (Por)Cl ₂ ]‐Catalyzed C–N Bond Formation: Spectroscopic Characterization, Reactivity, and Catalytic Reactions
  作者：Dan‐Yan Hong、Yungen Liu、Liangliang Wu、Vanessa Kar‐Yan Lo、Patrick H. Toy、Siu‐Man Law、Jie‐Sheng Huang、Chi‐Ming Che

  DOI：10.1002/anie.202100668

  日期：2021.8.16

  bond formation reactions via acylnitrene transfer have recently attracted much attention, but direct detection of the proposed acylnitrenoid/acylimido M(NCOR) (R=aryl or alkyl) species in these reactions poses a formidable challenge. Herein, we report on Ru(NCOR) intermediates in C−N bond formation catalyzed by [RuIV(Por)Cl2]/N3COR, a catalytic method applicable to aziridine/oxazoline formation from

  通过酰基硝烯转移的金属催化的 CN 键形成反应最近引起了很多关注，但在这些反应中直接检测所提出的酰基硝烯/酰基酰亚胺 M(NCOR)（R = 芳基或烷基）物质是一项艰巨的挑战。在此，我们报告了由 [Ru IV (Por)Cl 2 ]/N 3 COR 催化形成 CN 键的 Ru(NCOR) 中间体，这是一种适用于从烯烃形成氮丙啶/恶唑啉、取代吲哚胺化、α -由甲硅烷基烯醇醚形成氨基酮，C(sp 3)−H 键，以及天然产物和碳水化合物衍生物的功能化（产率高达 99%）。实验研究，包括 HR-ESI-MS 和 EPR 测量，加上 DFT 计算，为 Ru(NCOR) 酰基硝烯类化合物作为 Ru V -imido 物种的配方提供了证据。
• Toward a rational design of the assembly structure of polymetallic asymmetric catalysts: design, synthesis, and evaluation of new chiral ligands for catalytic asymmetric cyanation reactions
  作者：Ikuo Fujimori、Tsuyoshi Mita、Keisuke Maki、Motoo Shiro、Akihiro Sato、Sanae Furusho、Motomu Kanai、Masakatsu Shibasaki

  DOI：10.1016/j.tet.2007.02.081

  日期：2007.6

  New chiral ligands (4 and 5) for polymetallic asymmetric catalysts were designed based on the hypothesis that the assembled structure should be stable when made from a stable module 8. A metal-ligand 5:6+mu-oxo+OH complex was generated from Gd((OPr)-Pr-i)(3) and 4 or 5, and this complex was an improved asymmetric catalyst for the desymmetrization of meso-aziridines with TMSCN and conjugate addition of TMSCN to alpha,beta-unsaturated N-acylpyrroles, compared to the previously reported catalysts derived from 1-3. These two groups of catalysts produced opposing enantioselectivity even though the ligands had the same chirality. The functional difference in the asymmetric catalysts is derived from differences in the higher-order structure of the polymetallic catalysts. (C) 2007 Elsevier Ltd. All rights reserved.
• Catalytic Enantioselective Desymmetrization of <i>meso</i>-<i>N</i>-Acylaziridines with TMSCN
  作者：Tsuyoshi Mita、Ikuo Fujimori、Reiko Wada、Jianfeng Wen、Motomu Kanai、Masakatsu Shibasaki

  DOI：10.1021/ja053486y

  日期：2005.8.1

  A catalytic enantioselective desymmetrization of meso-N-p-nitrobenzoylaziridines with TMSCN was developed using a chiral gadolinium catalyst generated from Gd(OiPr)3 and d-glucose-derived ligand 1. In this reaction, the addition of a catalytic amount of trifluoroacetic acid (TFA) improved enantioselectivity. High enantioselectivity was obtained from a range of meso-aziridines at 0-60 degrees C. The product could be easily transformed into beta-amino acids. Thus, the developed catalytic enantioselective desymmetrization reaction allowed for efficient catalytic synthesis of chiral cyclic beta-amino acids. The incorporation of TFA into the catalyst complex was observed using ESI-MS. Generation of this new complex might be the origin of the improved enantioselectivity.