Trans-2-methyl-3-phenylisoxazolidine-5-carbonitrile

• 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: Trans-2-methyl-3-phenylisoxazolidine-5-carbonitrile
• 英文别名: (3S,5S)-2-methyl-3-phenyl-1,2-oxazolidine-5-carbonitrile
• 化学式: C₁₁H₁₂N₂O
• 分子量: 188.229
• InChiKey: OHYKONFYCOMUDI-QWRGUYRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  三甲基氰硅烷 、 5-(tert-butyldimethylsiloxy)-2-methyl-3-phenylisoxazolidine 在 三氟甲磺酸三甲基硅酯 作用下， 以 氯仿 为溶剂， 反应 8.0h， 生成 (3R*,5S*)-5-cyano-2-methyl-3-phenylisoxazolidine 、 Trans-2-methyl-3-phenylisoxazolidine-5-carbonitrile
  参考文献：
  名称：

  三甲基甲硅烷基三氟甲磺酸酯与硅烷基烯醇醚促进的硝基环加成反应：5-甲硅烷氧基异恶唑烷的合成与反应性

  摘要：

  在三甲基甲硅烷基三氟甲磺酸酯（TMSOTf）的存在下，硝酮与甲硅烷基烯醇醚的反应在温和条件下以良好或优异的收率提供了5-甲硅烷氧基异恶唑烷。5-Siloxyisoxazolidines可以进行化学选择性还原成Manoich碱或N-羟基-1,3-氨基醇，并且在TMSOTf存在下，与甲硅烷基化碳亲核试剂在乙缩醛C-5碳上反应，生成例如5-烯丙基和5-氰基异恶唑烷。

  DOI：

  10.1039/p19930003157

文献信息

• 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.
• Mukai, Chisato; Kim, In Jong; Cho, Won Jea, Journal of the Chemical Society. Perkin transactions I, 1993, p. 2495 - 2504
  作者：Mukai, Chisato、Kim, In Jong、Cho, Won Jea、Kido, Masaru、Hanaoka, Miyoji

  DOI：——

  日期：——
• Regioselectivity associated with the 1,3-dipolar cycloaddition of nitrones with electron-deficient dipolarophiles
  作者：Albert Padwa、Lubor Fisera、Konrad F. Koehler、Augusto Rodriguez、George S. K. Wong

  DOI：10.1021/jo00176a012

  日期：1984.1