(4S)-3-[(E)-4,4,4-trifluorobut-2-enoyl]-4-isopropyl-2-oxazolidinone | 288577-12-8

• 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: (4S)-3-[(E)-4,4,4-trifluorobut-2-enoyl]-4-isopropyl-2-oxazolidinone
• 英文别名: N-trifluorocrotonoyl-oxazolidin-2-one；(4S)-3-(4,4,4-Trifluoro-2-butenoyl)-4beta-isopropyloxazolidine-2-one；(4S)-4-propan-2-yl-3-[(E)-4,4,4-trifluorobut-2-enoyl]-1,3-oxazolidin-2-one
• CAS: 288577-12-8
• 化学式: C₁₀H₁₂F₃NO₃
• 分子量: 251.205
• InChiKey: YRBQOKYILMYTCP-KGGZQZJCSA-N

物化性质

• 沸点：
  275.8±50.0 °C(Predicted)
• 密度：
  1.296±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  L-缬氨醇 、 (4S)-3-[(E)-4,4,4-trifluorobut-2-enoyl]-4-isopropyl-2-oxazolidinone 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以72%的产率得到
  参考文献：
  名称：

  Conjugated additions of amines and β-amino alcohols to trifluorocrotonic acid derivatives: synthesis of ψ[NHCH(CF3)]-retro-thiorphan

  摘要：

  The aza-Michael addition of amines and beta-amino-alcohols to trifluorocrotonic acid derivatives is described. The reactions occurred in good to excellent yields, but low stereocontrol. The title reaction has been used as a key step for the synthesis of trifluoroethylamine mimics of retro-thiorphan, which showed low inhibitory activity of NEP (constant inhibition at the molar level). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.11.124

文献信息

• Synthesis, Structure and Conformation of Partially-Modified Retro- and Retro-Inversoψ[NHCH(CF3)]Gly Peptides
  作者：Alessandro Volonterio、Stefano Bellosta、Fabio Bravin、Maria Cristina Bellucci、Luca Bruché、Giorgio Colombo、Luciana Malpezzi、Stefania Mazzini、Stefano V. Meille、Massimiliano Meli、Carmen Ramírez de Arellano、Matteo Zanda

  DOI：10.1002/chem.200304881

  日期：2003.9.22

  sp(3) bonds in the [CO-CH(2)-CH(CF(3))-NH-CH(R)-CO] module, which is biased by the stereoelectronically demanding CF(3) group and the R side chain; 2) formation of nine-membered intramolecularly hydrogen-bonded rings, which have been clearly detected both in CHCl(3) solution and in some crystal structures. The former factor seems to be more important, as turn-like conformations were found in the solid-state

  psi [NHCH（CF（3））] Gly肽，部分概念修饰的逆肽（PMR）和逆反（PMRI）肽，是一类概念上新型的拟肽，已通过Aza-Michael反应合成了宽结构多样性和可变长度的肽对映体纯的α-氨基酯和对映体和几何纯的N-4,4,4-三氟巴豆酰基-恶唑烷-2-酮。已经研究了观察到的中等到良好非对映控制的基础因素。已通过溶液的MD计算支持（1）H NMR光谱研究了溶液中模型PMR-psi [NHCH（CF（3））] Gly三肽的构象，并通过X射线衍射研究了其固态。可以证明，与亲本基于丙二酰基的逆向肽相比，turn-like构象具有显着的稳定性，这可能是由于以下两个主要因素造成的：1）对[CO-CH（2）-CH（CF（3））-NH-CH（R）-CO]模块中sp（3）键的严格扭转限制，这受立体电子要求的CF（3）的偏见）基团和R侧链；2）形成的九元分子内氢键环，已经清楚地在CHCl（3）溶液
• Synthesis of Partially Modified Retro and Retroinverso ψ[NHCH(CF₃)]-Peptides
  作者：Alessandro Volonterio、Pierfrancesco Bravo、Matteo Zanda

  DOI：10.1021/ol005876p

  日期：2000.6.1

  Asymmetric conjugate additions of chiral alpha-amino esters to chiral 4-CF3 Michael-acceptors were exploited to prepare a small library of enantiomerically pure partially modified retropeptides having a psi[NHCH(CF3)] unit as a possible mimic of the classical psi(NHCO) retropeptide unit. Yields were nearly quantitative, and the stereoselectivity, which is controlled mainly by the nitrogen nucleophile, was progressively higher with increasing the steric bulk of the alpha-amino ester side-chain R-1.
• Synthesis of fluoromethylated materials in ionic liquids
  作者：Tomoya Kitazume、Kenji Tamura、Zaiju Jiang、Noriak Miyake、Isamu Kawasaki

  DOI：10.1016/s0022-1139(02)00006-4

  日期：2002.5

  Syntheses of fluoromethylated materials via Michael additions with the Baylis-Hillman type reaction and the reaction of fluoromethylated imines with enamines in ionic liquid are described. (C) 2002 Elsevier Science B.V. All rights reserved.
• US7390826B2
  申请人：——

  公开号：US7390826B2

  公开（公告）日：2008-06-24