(2R,3S)-N-(4-Methylphenylsulfonyl)-3-(2-methylpropyl)-2-vinylaziridine

• 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: (2R,3S)-N-(4-Methylphenylsulfonyl)-3-(2-methylpropyl)-2-vinylaziridine
• 英文别名: (2R,3S)-2-ethenyl-1-(4-methylphenyl)sulfonyl-3-(2-methylpropyl)aziridine
• 化学式: C₁₅H₂₁NO₂S
• 分子量: 279.403
• InChiKey: UNYSBAHRXUDMKM-YSPPHNQVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  45.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-叔丁氧羰基-L-亮氨醇 在 氢氧化钾 、 四(三苯基膦)钯 、 草酰氯 、 sodium hydride 、 二甲基亚砜 、 N,N-二异丙基乙胺 、 三苯基膦 、 zinc(II) chloride 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 61.0h， 生成 (2R,3S)-N-(4-Methylphenylsulfonyl)-3-(2-methylpropyl)-2-vinylaziridine
  参考文献：
  名称：

  A Thermodynamic Preference of Chiral N-Methanesulfonyl and N-Arenesulfonyl 2,3-cis-3-Alkyl-2-Vinylaziridines over Their 2,3-Trans-Isomers:  Useful Palladium(0)-Catalyzed Equilibration Reactions for the Synthesis of (E)-Alkene Dipeptide Isosteres

  摘要：

  Palladium(0)-catalyzed reactions of N-methanesulfonyl- or N-(arenesulfonyl)-3-alkyl-2-vinylaziridines reveal that 2,3-cis-isomers are more stable than the corresponding 2,3-trans-isomers in accord with ab initio calculations. A highly stereoselective synthetic route to (E)-alkene dipeptide isosteres having desired stereochemistries from 2,3-cis-3-isobutyl-2-vinylaziridine by the use of organocopper chemistry is also presented.

  DOI：

  10.1021/jo961760o

文献信息

• An unusual thermodynamic preference of chiral N-arylsulfonyl cis-3-alkyl-2-vinylaziridines over their trans-isomers: palladium(0)-catalysed equilibration reactions
  作者：Norio Mimura、Toshiro Ibuka、Masako Akaji、Yoshihisa Miwa、Tooru Taga、Kazuo Nakai、Hirokazu Tamamura、Nobutaka Fujii、Yoshinori Yamamoto

  DOI：10.1039/cc9960000351

  日期：——

  Palladium (0)-catalysed reactions of N-alkylsulfonyl- or N-arylsulfonyl-3-alkyl-2-vinyfaziridines reveal that 2,3-cis-isomers are more stable than the corresponding 2,3-trans-isomers in accord with ab initio calculations.

  钯(0)催化的N-烷基磺酰或N-芳基磺酰-3-烷基-2-乙烯基唑烷反应表明，2,3-顺式异构体比相应的2,3-反式异构体更稳定，这与从头计算的结果一致。
• A 2,3-cis-selective synthesis of aziridines bearing a vinyl group from allyl methyl carbonates and allyl mesylates
  作者：Hiroaki Ohno、Kiyonori Ishii、Asami Honda、Hirokazu Tamamura、Nobutaka Fujii、Yoshiji Takemoto、Toshiro Ibuka

  DOI：10.1039/a806882h

  日期：——

  A convenient method for the synthesis of synthetically useful chiral 2-vinylaziridines from natural α-amino acids is described. Satisfactory 2,3-cis-selectivities are obtained by exposure of methyl carbonates of various allylic alcohols bearing an N-protected amino group to a catalytic amount of tetrakis(triphenylphosphine)palladium(>0>), Pd(PPh3)4, in aprotic solvents such as THF. Base-promoted aziridination of mesylates of various N-protected amino allylic alcohols followed by Pd(PPh3)4 catalyzed isomerization for the 2,3-cis-selective synthesis of vinylaziridines is also presented.

  描述了一种从天然 α-氨基酸合成有用的手性 2-乙烯基氮丙啶的简便方法。通过将带有 N-保护氨基的各种烯丙醇的碳酸甲酯暴露于催化量的四(三苯基膦)钯(>0>)、Pd(PPh3)4，在非质子传递中获得令人满意的 2,3-顺式选择性。溶剂，例如THF。还介绍了各种 N-保护的氨基烯丙醇的甲磺酸酯的碱促进氮丙啶化，然后通过 Pd(PPh3)4 催化异构化，用于乙烯基氮丙啶的 2,3-顺式选择性合成。
• Ishii, Kiyonori; Ohno, Hiroaki; Takemoto, Yoshiji, Journal of the Chemical Society. Perkin transactions I, 1999, # 15, p. 2155 - 2163
  作者：Ishii, Kiyonori、Ohno, Hiroaki、Takemoto, Yoshiji、Osawa, Eriko、Yamaoka, Yumiko、Fujii, Nobutaka、Ibuka, Toshiro

  DOI：——

  日期：——
• Ishii, Kiyonori; Ohno, Hiroaki, Synlett, 1999, # 2, p. 228 - 230
  作者：Ishii, Kiyonori、Ohno, Hiroaki

  DOI：——

  日期：——
• A Thermodynamic Preference of Chiral <i>N</i>-Methanesulfonyl and <i>N</i>-Arenesulfonyl 2,3-<i>cis</i>-3-Alkyl-2-Vinylaziridines over Their 2,3-<i>Trans</i>-Isomers:  Useful Palladium(0)-Catalyzed Equilibration Reactions for the Synthesis of (<i>E</i>)-Alkene Dipeptide Isosteres
  作者：Toshiro Ibuka、Norio Mimura、Hiroshi Aoyama、Masako Akaji、Hiroaki Ohno、Yoshihisa Miwa、Tooru Taga、Kazuo Nakai、Hirokazu Tamamura、Nobutaka Fujii、Yoshinori Yamamoto

  DOI：10.1021/jo961760o

  日期：1997.2.1

  Palladium(0)-catalyzed reactions of N-methanesulfonyl- or N-(arenesulfonyl)-3-alkyl-2-vinylaziridines reveal that 2,3-cis-isomers are more stable than the corresponding 2,3-trans-isomers in accord with ab initio calculations. A highly stereoselective synthetic route to (E)-alkene dipeptide isosteres having desired stereochemistries from 2,3-cis-3-isobutyl-2-vinylaziridine by the use of organocopper chemistry is also presented.