methyl (4R,5S,2Z)-4,5-epimino-N-<(4-methylphenyl)sulfonyl>hex-2-enoate | 158195-22-3

• 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: methyl (4R,5S,2Z)-4,5-epimino-N-<(4-methylphenyl)sulfonyl>hex-2-enoate
• 英文别名: (2R,3S)-N-Tosyl-2-<(Z)-2-(methoxycarbonyl)ethenyl>-3-methylaziridine；methyl (Z)-3-[(2R,3S)-3-methyl-1-(4-methylphenyl)sulfonylaziridin-2-yl]prop-2-enoate
• CAS: 158195-22-3
• 化学式: C₁₄H₁₇NO₄S
• 分子量: 295.359
• InChiKey: CCBZBLUNHZKKAA-MBGNOEIWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  71.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (4R,5S,2Z)-4,5-epimino-N-<(4-methylphenyl)sulfonyl>hex-2-enoate 在 二异丁基氢化铝 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 18.75h， 生成 (2S,5S)-(E)-5-[N-(p-toluenesulfonyl)amino]-2-methylhex-3-enol
  参考文献：
  名称：

  Fujii, Nobutaka; Nakai, Kazuo; Tamamura, Hirokazu, Journal of the Chemical Society. Perkin transactions I, 1995, # 11, p. 1359 - 1372

  摘要：

  DOI：
• 作为产物：
  描述：

  (2S,3S)-2-hydroxymethyl-3-methyl-1-<(4-methylphenyl)sulfonyl>aziridine 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 methyl (4R,5S,2Z)-4,5-epimino-N-<(4-methylphenyl)sulfonyl>hex-2-enoate
  参考文献：
  名称：

  SN2'-Reactions of Peptide Aziridines. A Cuprate-Based Approach to (E)-Alkene Isosteres

  摘要：

  Alkenylaziridines were prepared from allylic alcohols via Sharpless epoxidation; oxirane to aziridine conversion under modified Staudinger conditions, and Wittig chain extension. Alternatively, beta-hydroxy alpha-amino acids such as threonine can serve as readily available precursors. The corresponding N-acyl, -peptidyl-, -carbamoyl-, and -sulfonylaziridines underwent a high-yielding anti-S(N)2' alkylation with organocopper/BF3 complex to give (E)-alkene peptide isosteres in 62 to >98% de. The stereoselectivity of the addition process was studied by H-1 and F-19 NMR as well as chemical degradation. Alkene isosteres are important nonhydrolyzable and rigidified analogs of peptide bonds in biologically active peptides. This new methodology considerably facilitates the synthesis and the study of these peptide mimetics, since alkenylaziridines are readily prepared and side-chain modification is simplified by the wide range of functionalized organocopper reagents that are available.

  DOI：

  10.1021/jo00096a033

文献信息

• A thermodynamic preference of chiral cis-γ,δ-epimino-(E)-α,β-unsaturated esters over other stereoisomers: Synthetically useful Pd(0)-catalyzed equilibrated reactions of aziridines bearing an α,β-unsaturated ester group
  作者：Toshiro Ibuka、Masako Akaji、Norio Mimura、Hiromu Habashita、Kazuo Nakai、Hirokazu Tamamura、Nobutaka Fujii、Yoshinori Yamamoto

  DOI：10.1016/0040-4039(96)00403-0

  日期：1996.4

  A practical synthesis of chiral N-arylsulfonyl-cis-γ,δ-epimino-(E)-α,β-enoates, key intermediates for the synthesis of (E)-alkene dipeptide isosteres via Pd(0)-catalyzed equilibrated reactions, has been successfully achieved by exposing N-arylsulfonyl-γ,δ-epimino-α,β-unsaturated esters to a catalytic amount of Pd(PPh3)4 in THF at 0 ∼ 20 °C.

  手性的实用合成Ñ -arylsulfonyl-顺- γ，δ -epimino-（ë） - α，β -enoates，对（合成关键中间体ë） -烯烃电子等排体的二肽通过钯（0）催化的平衡反应，通过将N-芳基磺酰基-γ，δ-表-氨基-α，β-不饱和酯暴露于催化量的Pd（PPh 3）4在THF中的温度为0到20°C，可以成功地实现这一目的。
• Ibuka, Toshiro; Nakai, Kazuo; Habashita, Hiromu, Angewandte Chemie, 1994, vol. 106, # 6, p. 693 - 695
  作者：Ibuka, Toshiro、Nakai, Kazuo、Habashita, Hiromu、Hotta, Yuka、Fujii, Nobutaka、et al.

  DOI：——

  日期：——