5-cyano-2,3-diphenylisoxazolidine | 19380-25-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 5-cyano-2,3-diphenylisoxazolidine
• 英文别名: cis-2,3-Diphenyl-5-cyan-isoxazolidin；2,3c-diphenyl-isoxazolidine-5r-carbonitrile
• CAS: 19380-25-7；74555-37-6
• 化学式: C₁₆H₁₄N₂O
• 分子量: 250.3
• InChiKey: RHSGRUBZLVGBIZ-JKSUJKDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.46
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  36.26
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  丙烯腈 、 C,N-diphenylnitrone 反应 48.0h， 生成 5-cyano-2,3-diphenylisoxazolidine
  参考文献：
  名称：

  Huisgen,R. et al., Chemische Berichte, 1968, vol. 101, # 7, p. 2568 - 2584

  摘要：

  DOI：

文献信息

• Chemistry of unsaturated arenetricarbonylchromium compounds
  作者：N. Yu. Zarovkina、E. V. Sazonova、A. N. Artemov、G. K. Fukin

  DOI：10.1007/s11172-015-0956-9

  日期：2015.4

  1,3-Dipolar cycloaddition reactions of nitrones of a general formula RCH=N+(O–)R´, where R = Ph, Ph[Cr(CO)3], R´ = Me, Ph, But, with acrylonitrile were studied. The isoxazolidines obtained by these reactions were isolated and identified. The introduction in the nitrone molecule of a tricarbonylchromium group led to the increase in the regioand stereoselectivity of cycloaddition. The influence of deuterated solvents on chemical shifts of protons in the isoxazolidine ring was studied.

  研究了通式 RCH=N+(O–)R´ 的硝酮与丙烯腈的 1,3-偶极环加成反应，其中 R = Ph, Ph[Cr(CO)3], R´ = Me, Ph, But， 。分离并鉴定了通过这些反应获得的异恶唑烷。在硝酮分子中引入三羰基铬基团导致环加成的区域选择性和立体选择性增加。研究了氘代溶剂对异恶唑烷环中质子化学位移的影响。
• Asymmetric 1,3-dipolar cycloaddition reaction of α,β-unsaturated nitriles with nitrones catalyzed by chiral-at-metal rhodium or iridium complexes
  作者：Daniel Carmona、M. Pilar Lamata、Fernando Viguri、Ricardo Rodríguez、Fernando J. Lahoz、M. José Fabra、Luis A. Oro

  DOI：10.1016/j.tetasy.2009.04.002

  日期：2009.6

  The aqua complexes (S-M,R-C)-[(eta(5)-C5Me5)M(R)-Prophos}(H2O)](SbF6)(2) (M = Rh, Ir; (R)-Prophos = 1,2-bisdiphenylphosphino propane) catalyze the 1,3-dipolar cycloaddition reaction (DCR) of nitrones with alpha,beta-unsaturated nitriles with low-to-moderate enantioselectivity. The involved catalysts [(eta(5)-C5Me5)M(R)-Prophos}(alpha,beta-unsaturated nitrile)](SbF6)(2), isolated as mixtures of the (S-M,R-C)- and (R-M,R-C)-diastereomers, have been fully characterized, and the molecular structure of the complexes (S-Rh,R-C)-[eta(5)-C5Me5)Rh(R)-Prophos}(cis-2-pentenenitrile)](SbF6)(2) and (S-Ir,R-C)-[eta(5)-C5Me5)Ir(R)-Prophos}(acrylonitrile)](SbF6)(2) has been determined by X-ray diffraction. The (R)-at-metal epimers isomerize to the (S)-at-metal counterparts. Diastereopure (S-M,R-C)-[(eta(5)-C5Me5)M(R)-Prophos)(alpha,beta-unsaturated nitrile)](SbF6)(2) complexes catalyze the above-mentioned DCR in a stoichiometric manner with Lip to 97% ee. The results make clear the influence of the metal configuration on the catalytic stereochemical Outcome. The catalysts can be recycled without significant loss of either activity or selectivity. (C) 2009 Elsevier Ltd. All rights reserved.